Co-reporter:Xi Luo, Fen Wu, Haibin Xiao, Huan Guo, Yijiang Liu, Songting Tan
Synthetic Metals 2017 Volume 223() pp:205-211
Publication Date(Web):January 2017
DOI:10.1016/j.synthmet.2016.11.026
•Zinc-porphyrin was introduced into copolymers as pendant group.•Four copolymers with DPP and zinc-porphyrin (ZP) derivatives were synthesized.•Copolymer P(ZP-BT-DPP4) gave a power conversion efficiency of 2.44%.A series of copolymers containing zinc porphyrin (ZP) derivatives as pendant groups and diketopyrrolopyrrole (DPP) as electron-withdrawing units were designed and synthesized by Stille-coupling polymerization. The introduction of zinc porphyrin derivatives enhances the light-harvesting capability and leads to a complementary absorption at short wavelength band. The absorption of the copolymers can be well-tuned by varying the ratio of zinc porphyrin derivatives and DPP units. The results indicated that copolymer P(ZP-BT-DPP4) with ZP/DPP ratio of 1:4 showed an strong absorption in the range of 400–900 nm. The power conversion efficiency (PCE) of 2.44% with an increased Jsc of 6.14 mA/cm2 was achieved due to the better light-harvesting ability and suitable active film morphology.
Co-reporter:Zhaoxia Liu, Keke Duan, Huan Guo, Yanghua Deng, Hongli Huang, Xuanying Yi, Huajie Chen, Songting Tan
Dyes and Pigments 2017 Volume 140(Volume 140) pp:
Publication Date(Web):1 May 2017
DOI:10.1016/j.dyepig.2017.01.026
•The three dyes were synthesized and applied in dye-sensitized solar cells.•By adding the auxiliary acceptor into dyes, the Jsc increased 50% (from 8.16 to 12.22 mA cm−2).•The dye based on DPP as the auxiliary acceptor obtained a PCE of 5.19%.Three novel D–A–π–A organic dyes (D1, D2, and D3) based on triarylamine donor (IDTTPA) as the electron donor and benzoic acid as the anchoring group have been successfully synthesized for dye-sensitized solar cells (DSSCs). To fine-tune absorption spectra, energy level structures, and photovoltaic properties of the target dyes, auxiliary acceptors including benzothiadiazole or diketopyrrolopyrrole units are also introduced into the dye backbones. It is found that the DPP-containing dye D3 exhibits a higher molar extinction coefficient, stronger light-capturing ability, and better photovoltaic performance than those of D1 and D2 dyes. Investigation of the photovoltaic performances shows that the D3-based DSSCs afford the highest power conversion efficiency (PCE) values of up to 5.19%, higher than those of the D1-based DSSCs (4.23%) and D2-based DSSCs (4.99%). This work has demonstrated that the incorporation of auxiliary acceptors into the IDTTPA-based organic dyes can effectively manipulate absorption band, charge recombination, and photovoltaic peformance of DSSCs.Download high-res image (225KB)Download full-size image
Co-reporter:Guo Wang, Zhaoxia Liu, Yanghua Deng, Lingchao Xie, Songting Tan
Dyes and Pigments 2017 Volume 145(Volume 145) pp:
Publication Date(Web):1 October 2017
DOI:10.1016/j.dyepig.2017.06.027
•Two new dyes were synthesized and applied in dye-sensitized solar cells.•The dye XD1 containing DFBT as auxiliary acceptor achieved high relatively Voc.•The dye XD2 containing DPP achieve higher Jsc result from its wider absorption.•The dye XD2 with 1 mM CDCA as co-adsorbent obtained a PCE of 6.14%.We report the synthesis and DSSCs performance of two dye sensitizers XD1 and XD2 with D-π-A1-π-A2 structure bearing difluorobenzo[c][1,2,5]thiadiazole (DFBT) and diketopyrrolopyrrole (DPP)-based as auxiliary acceptor moieties. The effect of DFBT or DPP on the photophysical, electrochemical, and photovoltaic properties of the target dyes were investigated. It is found that DPP-containing XD2 achieve higher Jsc result from its wider absorption spectrum ranging from visible to near-infrared region, higher molar absorption coefficient in the low-energy region and stronger photocurrent generation as compared to the DFBT-containing XD1. Additionally, the longer electron lifetime and increased charge recombination resistance of XD1 make it achieves higher Voc. The photovoltaic properties of the DSSCs are synthetically influenced by Jsc and Voc. Eventually, the investigation of photovoltaic performance of DSSCs indicates that XD1 obtains slightly higher power conversion efficiency (PCE) of 5.04%, but the PCE of the DSSCs based on the dye XD2 with 1 mM CDCA as co-adsorbent is increased to 6.14%.Download high-res image (160KB)Download full-size image
Co-reporter:Zhaokui Zeng;Zhiquan Zhang;Bin Zhao;Hailu Liu;Xiai Sun;Guo Wang;Jian Zhang
Journal of Materials Chemistry A 2017 vol. 5(Issue 16) pp:7300-7304
Publication Date(Web):2017/04/18
DOI:10.1039/C7TA00495H
A copolymer with A–A structure is rationally designed and synthesized by using difluorobenzo[c]-cinnoline (DFBC) as weak electron-withdrawing (A) moieties and 1,4-diketo-pyrrolo[3,4-c]pyrrole (DPP) as strong A moieties. Polymer solar cells based on PDFBC-DPP and PC71BM showed a promising power conversion efficiency of 7.92%, which is one of the highest values in polymer solar cells based on A–A structure.
Co-reporter:Chao Weng, Huan Guo, Zhiquan Zhang, Jian Zhang, Bin Zhao, Songting Tan
Dyes and Pigments 2017 Volume 143(Volume 143) pp:
Publication Date(Web):1 August 2017
DOI:10.1016/j.dyepig.2017.04.052
•Three terpolymers were synthesized and applied in polymer solar cells.•By changing DPP/DTffBT ratio, the photovoltaic performances of terpolymers were improved.•The device based on regular terpolymer re-P3 exhibited a PCE of 4.08%.Three new random or regular terpolymers (ra-P1, re-P2, and re-P3) based on diketopyrrolopyrrole (DPP) and 5,6-difluorobenzo-[c][1,2,5]thiadiazole (ffBT) as electron-deficient unit (A), alkylthienyl-substituted benzodithiophene (BDTT) as electron-rich units (D) have been designed and synthesized for donor materials in polymer solar cells. The differences on photophysical, electrochemical, and photovoltaic properties of these terpolymers have been investigated. Compared with random terpolymer ra-P1, regular terpolymer re-P2 has stronger absorption band range from 300 to 800 nm, higher hole mobility and more appropriate surface morphology. With increasing the quantity of DTffBT, regular terpolymer re-P3 showed more stronger absorption band in 300–600 nm compared to re-P2. The polymer solar cells have been fabricated by using these terpolymers as donor materials and [6,6]-phenyl-C71-butyric acid methyl ester (PC71BM) as the acceptor material. Among them, the device based on re-P3 demonstrated preferable power conversion efficiency of 4.08% with a short-circuit current of 8.23 mA cm−2, an open-circuit voltage of 0.76 V and a fill factor of 65.0%.
Co-reporter:Hongli Huang, Huajie Chen, Jun Long, Guo Wang, Songting Tan
Journal of Power Sources 2016 Volume 326() pp:438-446
Publication Date(Web):15 September 2016
DOI:10.1016/j.jpowsour.2016.06.099
•A novel electron rich group (IDTTPA) with a 3D structure was synthesized.•Two organic dyes with D-A-π -A structure were synthesized and applied in DSSCs.•The organic dye CD2 based on IDTTPA showed a high PCE of 7.90%.Organic dyes with a 3-dimensional (3D) structure is helpful for retarding dyes aggregation and charge recombination as well as improving the power conversion efficiency (PCE) of dye-sensitized solar cells (DSSCs). In this contribution, a novel 3D triarylamine derivative (IDTTPA) featuring an indenothiophenene unit has been designed, synthesized, and applied to develop a 3D organic dyes. Two novel D–A–π–A organic dyes (CD1 and CD2) based on IDTTPA as the electron donors, 2,1,3-benzothiadiazole derivatives as the auxiliary acceptors, and formic acid as the anchoring groups have been successfully synthesized and applied in DSSCs. The effects of the fluoro substitute groups on the photophysical, electrochemical, and photovoltaic properties are investigated. The results indicate that the fluoro-containing dye CD2 exhibits higher molar extinction coefficient, stronger light-capturing ability, and better photovoltaic performance than those of CD1 dye without fluoro substitute. Investigation of the DSSCs performance shows that CD2-based DSSCs exhibit a high PCE value of 7.91%, higher than that of CD1-based DSSCs (6.29%), even higher than that of the reference DSSCs based on N719 (7.49%). This works has demonstrated that this kind of 3D unit (IDTTPA) is a strong and promising electron donor unit to develop high efficiency metal-free organic dyes.
Co-reporter:Huan Guo, Chao Weng, Guo Wang, Bin Zhao, Songting Tan
Dyes and Pigments 2016 Volume 133() pp:16-24
Publication Date(Web):October 2016
DOI:10.1016/j.dyepig.2016.05.045
•The five copolymers were synthesized and applied in polymer solar cells.•The terpolymer PBDTT-DPP-TTDPP obtained a PCE of 4.46%.•The binary copolymer PBDTT-TTDPP obtained a PCE of 4.74% after THF vapor annealing.A series of donor–acceptor conjugated polymers based on the alkylthienyl-benzodithiophene (BDTT) as an electron-rich unit, and diketopyrrolopyrrole (DPP) incorporated in backbone or side chain as electron-deficient units have been synthesized and applied in polymer solar cells. Compared with the binary copolymers, random terpolymers exhibit a broader absorption range. By controlling the ratio of the electron-deficient units, both photophysical, electrochemical properties, lamellar distance, π−π* stacking distance and the photovoltaic properties of the random terpolymers were changed dramatically. Bulk heterojunction polymer solar cells based on the copolymers as the electron donors and (6,6)-phenyl-C61-butyric acid methyl ester as the acceptor were fabricated. The power conversion efficiency of 4.46% was obtained from the terpolymer (PBDTT-DPP-TTDPP). Optimization via solution vapor annealing, the binary copolymer (PBDTT-TTDPP) showed the best power conversion efficiency of 4.74% with a short-circuit current of 10.63 mA cm−2, a high open-circuit voltage of 0.88 V and a fill factor of 51.0%.Figure optionsDownload full-size imageDownload as PowerPoint slide
Co-reporter:Jun Long, Xunshan Liu, Huan Guo, Bin Zhao, Songting Tan
Dyes and Pigments 2016 Volume 124() pp:222-231
Publication Date(Web):January 2016
DOI:10.1016/j.dyepig.2015.09.025
•The three dyes with conjugated side groups on thiophene π-bridge were designed and synthesized.•The photovoltaic properties can be regulated by introducing different conjugated side groups.•The LD2-based dye showed a relatively high PCE of 7.41%.Three novel organic dyes (LD1, LD2 and LD3) with conjugated side groups on the thiophene π-bridge are designed and synthesized for dye sensitized solar cells (DSSCs). The photophysical, electrochemical, and photovoltaic properties of the dyes have been successfully tuned by incorporating different conjugated side groups into the thiophene π-bridges moieties of dyes. Compared with the analogous dyes with non-conjugated side groups, the side group-conjugated dyes exhibited wider absorption spectra, higher molar extinction coefficients, and better photovoltaic performances. For the LD2-based DSSCs, the maximum power conversion efficiency (PCE) of 7.71% is obtained under AM 1.5 G irradiation (100 mW cm−2). The result demonstrates that high-performance DSSCs can be acquired by choosing suitable conjugated side groups into the π-bridges moieties of organic dyes.
Co-reporter:Huan Guo, Tianpei Shen, Fen Wu, Guo Wang, Linglong Ye, Zhaoxia Liu, Bin Zhao and Songting Tan
RSC Advances 2016 vol. 6(Issue 16) pp:13177-13184
Publication Date(Web):19 Jan 2016
DOI:10.1039/C5RA23863C
A series of D1–A–D2–A terpolymers based on diketopyrrolopyrrole (DPP) as electron-deficient unit (A), alkylthienyl-substituted benzodithiophene (BDTT) and thiophene-2,5-bis(2-alkyloxy)benzene-thiophene (TBT) as electron-rich units (D) have been designed and synthesized by Stille-coupling reaction. The effects of the TBT/BDTT ratios on the thermal, photophysical, electrochemical properties and crystallinity of the copolymers were investigated using thermogravimetric analysis, UV-vis-NIR absorption spectra, cyclic voltammetry and wide-angle X-ray diffraction, respectively. Compared with the binary copolymers (PDPPHT-TBT and PDPPHT-BDTT), the random terpolymers (PDPPHT-3TBT-BDTT, PDPPHT-TBT-BDTT and PDPPHT-TBT-3BDTT) exhibited significant improvement in thermal stability and hole mobility, and the optical, electrochemical properties, lamellar distance and π–π* stacking distance of the random terpolymers were successfully tuned with different TBT/BDTT ratios. Bulk heterojunction polymer solar cells based on the as-synthesized terpolymers as electron donors and (6,6)-phenyl-C61-butyric acid methyl ester (PC61BM) as the acceptor were fabricated. The best power conversion efficiency (PCE) of 4.18% was obtained from the terpolymer PDPPHT-TBT-BDTT.
Co-reporter:He Qiao, Yanghua Deng, Ruipeng Peng, Guo Wang, Jing Yuan and Songting Tan
RSC Advances 2016 vol. 6(Issue 74) pp:70046-70055
Publication Date(Web):19 Jul 2016
DOI:10.1039/C6RA11918B
Three ullazine-based organic sensitizers (QD1, QD2 and QD3) have been designed, synthesized, and characterized for dye-sensitized solar cells (DSSCs). Ullazine possesses some attractive properties, such as a planar π-system to promote intensely the intramolecular charge transfer (ICT) between ullazine donor units and cyanoacrylic acid or carboxylic acid acceptor units. The tuning of π-spacers and anchoring groups led to variation of the photovoltaic performances. The DSSC based on QD1 with a cyanoacrylic acid and ethylene, obtained a PCE of 5.28%, which was higher than that of QD2 with a carboxylic acid and phenylethylene, and QD3 with a carboxylic acid and thiophene ethylene. The absorption spectra of QD2 and QD3 with the increasing of the length of the π-spacers are blue-shifted compared to that of QD1. The absorbed amount of QD1 was the highest of all, contributing to the highest Jsc of 12.28 mA cm−2. The different Voc values, in the order of QD1 (0.65 V) > QD2 (0.60 V) > QD3 (0.53 V), are caused by the charge recombination rates at the TiO2/dye/electrolyte interface and the electron lifetimes.
Co-reporter:Huan Guo;Tianpei Shen;Fen Wu;Rongyan Hou;Xuxu Liu;Bin Zhao
Journal of Applied Polymer Science 2016 Volume 133( Issue 6) pp:
Publication Date(Web):
DOI:10.1002/app.42982
ABSTRACT
Three new random conjugated terpolymers based on thiophene-2,5-bis((2- ethylhexyl)oxy)benzene-thiophene or thiophene-2,5-bis((2-octyl)oxy)benzene- thiophene as electron-donating units, diketopyrrolopyrrole (DPP) and 4,7-dithien-5-yl-2,1,3-benzothiadiazole (DTBT) side group as electron-withdrawing units have been designed and synthesized by Stille-coupling reaction. All the terpolymers exhibit good thermal stability, broad absorption in the range of 300 to 800 nm. By tuning the alkyl side chains of the terpolymers, the absorption spectra, HOMO energy levels and photovoltaic properties of the terpolymers changed dramatically. A bulk heterojunction polymer solar cell fabricated from terpolymer GP2 and PC61BM exhibited a promising power conversion efficiency of 3.31% without any processing additives. © 2015 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2016, 133, 42982.
Co-reporter:Huajie Chen, Zhaoxia Liu, Zhiyuan Zhao, Liping Zheng, Songting Tan, Zhihong Yin, Chunguang Zhu, and Yunqi Liu
ACS Applied Materials & Interfaces 2016 Volume 8(Issue 48) pp:
Publication Date(Web):November 15, 2016
DOI:10.1021/acsami.6b12540
Five-membered 1,3,4-oxadiazole (OZ) and 1,3,4-thiadiazole (TZ) heterocycle-based copolymers as active layer have long been ignored in solution-processable n-channel polymer field-effect transistors (PFETs) despite the long history of using OZ or TZ derivatives as the electron-injecting materials in organic light-emitting devices and their favorable electron affinities. Herein, we first report the synthesis and PFETs performance of two n-channel conjugated polymers bearing OZ- or TZ-based acceptor moieties, i.e., PNOZ and PNTZ, where simple thiophene units are utilized as the weak donors and additional alkylated-naphthalenediimides units are used as the second acceptors. A comparative study has been performed to reveal the effect of different heterocyclic acceptors on thermal properties, electronic properties, ordering structures, and carrier transport performance of the target polymers. It is found that both polymers possess low-lying LUMO values below −4.0 eV, indicating high electron affinity for both heterocycle-based polymers. Because of strong polarizable ability of sulfur atom in TZ heterocycle, PNTZ exhibits a red shift in maximal absorption and stronger molecular aggregation even in the diluted chlorobenzene solution as compared to the OZ-containing PNOZ. Surface morphological study reveals that a nodule-like surface with a rough surface morphology is observed clearly for PNOZ films, whereas PNTZ films display highly uniform surface morphology with well interconnected fiber-like polycrystalline grains. Investigation of PFETs performance indicates that both polymers afford air-stable n-channel transport characteristics. The uniform morphological structure and compact π–π stacking endow PNTZ with a high electron mobility of 0.36 cm2 V–1 s–1, much higher than that of PNOZ (0.026 cm2 V–1 s–1). These results manifest the feasibility in improving electron-transporting property simply by tuning heteroatom substitutes in n-channel polymers; further demostrate that TZ derivatives possess much superior potential for developing high-performance n-channel polymers compared to OZ derivatives.Keywords: 1,3,4-oxadiazole; 1,3,4-thiadiazole; air-stable; high performance; n-channel field-effect transistors;
Co-reporter:Yuanshuai Huang;Linglong Ye;Fen Wu;Suli Mei;Huajie Chen
Journal of Polymer Science Part A: Polymer Chemistry 2016 Volume 54( Issue 5) pp:668-677
Publication Date(Web):
DOI:10.1002/pola.27888
ABSTRACT
Two novel acceptors of benzo[c][1,2,5]thiadiazole and quinoxaline with conjugated dithienylbenzothiadiazole pendants were first designed and synthesized for building efficient photovoltaic copolymers. Based on benzo[1,2-b;3,4-b′]dithiophene donors and the two acceptors, two new copolymers have been prepared by Stille coupling polymerization. The resulting copolymers were characterized by 1H NMR, gel permeation chromatography, and thermogravimetric analysis. UV–Visible absorption and cyclic voltammetry measurements indicated that the two copolymers possessed strong and broad absorption in the range of 300–700 nm, and deep-lying energy levels of highest occupied molecular orbitals. The polymer photovoltaic devices based on benzo[c][1,2,5]thiadiazole-based copolymer/phenyl-C71-butyric acid methyl ester exhibited a power conversion efficiency of 2.42%, attributed to its relatively better light-harvesting ability and active film morphology. © 2015 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2016, 54, 668–677
Co-reporter:Huifang Zhao, Jun Long, Xi Luo, Bin Zhao, Songting Tan
Dyes and Pigments 2015 Volume 122() pp:168-176
Publication Date(Web):November 2015
DOI:10.1016/j.dyepig.2015.06.024
•Three new D-π-A type unsymmetrical porphyrin dyes were synthesized.•2-Ethynyl-6-methylthieno[3,2-b]thiophene as π spacer broadened the absorption.•Dye BSF exhibited higher conversion efficiency than that of SF and NSF.In this study, three donor-π-acceptor (D-π-A) type unsymmetrical porphyrin-based dyes have been designed and synthesized for dye-sensitized solar cells (DSSCs). The photophysical, electrochemical and photovoltaic properties of the dyes were successfully adjusted by using functionalized arylamines (triphenylamine or N, N-dimethyl-4-(acetylene)-aniline) as donor, porphyrin derivatives as conjugated π bridge, ethynyl-thiophene or ethynyl-thiophthene as π spacer and carboxylic acid as anchor group. Compared with the dye containing ethynyl-thiophene as π spacer, the dyes containing 2-ethynyl-6-methylthieno[3,2-b]thiophene as π spacer between the porphyrin macrocycle and the carboxylic acid anchoring group show broadened absorption spectra on TiO2 films and red-shifted absorption spectra in solution. The dye based on triphenylamine and 2-ethynyl-6-methylthieno[3,2-b]thiophene exhibited a power conversion efficiency (PCE) of 4.53% under simulated air mass 1.5 global sunlight. These results indicate that the introduction of 2-ethynyl-6-methylthieno[3,2-b]thiophene in the meso-positions of porphyrin dyes is an effective approach to improve the photovoltaic performance.
Co-reporter:Xuxu Liu, Jun Long, Guo Wang, Yong Pei, Bin Zhao, Songting Tan
Dyes and Pigments 2015 Volume 121() pp:118-127
Publication Date(Web):October 2015
DOI:10.1016/j.dyepig.2015.05.012
•Three novel phenothiazine-based dyes were synthesized for DSSCs.•The DSSC device based on the dye DX1 obtained the highest PCE of 5.69%.•The dyes DX2 and DX3 displayed broad spectra responses.Three novel dyes DX1, DX2 and DX3 containing phenothiazine are designed and synthesized for dye-sensitized solar cells (DSSCs). Photophysical, electrochemical and photovoltaic properties of the three dyes have been systematically investigated. The results show that the DX1-based DSSC with 0.5 mM chenodeoxycholic acid (CDCA) obtains the power conversion efficiency (PCE) of 5.69%. When an additional electron-deficient benzothiadiazole (BT) unit is introduced into the molecular structures of the dyes DX2 and DX3, the absorption spectra are broadened. But the short-circuit photocurrent density (Jsc) of the devices are decreased due to the blocked electron transfer, so the DSSC device based on DX2 only obtains the PCE of 3.43%. Furthermore, a triphenylamine (TPA) unit with high electron-donating ability is joined onto the nitrogen atom of phenothiazine donor in DX3, which enhances the electron injection efficiency and reduces the dye aggregation. Thus, the Jsc is improved, resulting in a higher PCE of 4.41% in the DX3-based dye than the DX2-based one.
Co-reporter:Yuanshuai Huang, Fen Wu, Min Zhang, Suli Mei, Ping Shen, Songting Tan
Dyes and Pigments 2015 Volume 115() pp:58-66
Publication Date(Web):April 2015
DOI:10.1016/j.dyepig.2014.12.012
•A novel asymmetric SBDT unit was synthesized for the first time.•Two new copolymers, PSBDT–FBT and PSBDT–TID, were synthesized and applied in polymer solar cell.•PSCs based on the copolymer showed a high Voc of 0.92 V and a PCE of 5.0%.Two novel copolymers containing an asymmetric 4-(2-ethylhexyloxy)-8-(2-ethylhexylthio)benzo[1,2-b:4,5-b′]dithiophene and different conjugated side groups were designed and synthesized for polymer solar cell applications. The thermal, optical, and electrochemical properties were investigated by thermal gravimetric analysis, UV–Vis absorption, and cyclic voltammetry, respectively. The two copolymers showed a good thermal stability and solubility in common organic solvents, and relatively deep highest occupied molecular orbital (HOMO) energy levels with the values of −5.56 eV for 5,6-difluoro-benzodiathiazole-based copolymer and −5.48 eV for isoindigo-based copolymer. The polymer photovoltaic devices based on 5,6-difluoro-benzodiathiazole-based polymer/phenyl-C71-butyric acid methyl ester exhibited a high open circuit voltage (Voc) of 0.92 V and the power conversion efficiency of 5.0%.
Co-reporter:Suli Mei, Fen Wu, Yuanshuai Huang, Bin Zhao, Songting Tan
European Polymer Journal 2015 Volume 67() pp:31-39
Publication Date(Web):June 2015
DOI:10.1016/j.eurpolymj.2015.03.049
•Four copolymers with BDT and 3-ethylrhodanine side group were synthesized.•3-Ethylrhodanine was introduced into the copolymers as side group.•The PSC based on the copolymers showed a high Voc of 0.94 V.Four conjugated copolymers (PBDT-TRD, PBDT-3TRD, PBDT-TTRD, and PBDT-3TTRD) based on 3-ethylrhodanine in the side chains have been designed and synthesized. The effects of the conjugated π-bridge and 3-ethylrhodanine unit on absorption spectra, energy levels, and photovoltaic properties of the copolymers have been investigated. These copolymers exhibit good thermal stabilities, broad absorption spectra, and deep highest occupied molecular orbital (HOMO) energy levels. The polymer solar cells have been fabricated by using these copolymers as the donors and [6,6]-phenylC61-butyric acid methyl ester (PC61BM) as the acceptor. Among them, the devices based on PBDT-TRD and PBDT-TTRD demonstrated preferable power conversion efficiencies of 3.35% and 3.18% with high open-circuit voltages of 0.94 V and 0.85 V, respectively.
Co-reporter:Yuanshuai Huang, Min Zhang, Huajie Chen, Fen Wu, Zhencai Cao, Lingjun Zhang and Songting Tan
Journal of Materials Chemistry A 2014 vol. 2(Issue 15) pp:5218-5223
Publication Date(Web):21 Jan 2014
DOI:10.1039/C4TA00020J
Three novel random conjugated terpolymers were designed and synthesized by copolymerizing a benzo[1,2-b:4,5-b′]dithiophene (BDT) donor with an electron-deficient diketopyrrolo[3,4-c]pyrrole (DPP) unit and a thiophene-vinylene-dithienyl-benzothiadiazole (TVDTBT) side group into a polymer backbone. By tuning the ratio of DPP and TVDTBT in the terpolymers, the optical properties and energy levels of these random terpolymers could be rationally controlled. As a result, the terpolymers exhibited a very broad absorption range of 300–900 nm with a high absorption coefficient and deep HOMO energy levels. Bulk heterojunction polymer solar cells fabricated from P3 and PC61BM exhibited a promising power conversion efficiency of 5.29% without any processing additives.
Co-reporter:Min Zhang, Fen Wu, Zhencai Cao, Tianpei Shen, Huajie Chen, Xiangling Li and Songting Tan
Polymer Chemistry 2014 vol. 5(Issue 13) pp:4054-4060
Publication Date(Web):27 Feb 2014
DOI:10.1039/C3PY01664A
A series of donor–acceptor (D–A) conjugated random terpolymers were synthesized by copolymerizing electron-rich alkylthienyl-substituted benzodithiophene (BDTT) and two electron-deficient units, a diketopyrrolopyrrole (DPP) moiety and isoindigo (TID) based side chain. The effects of the DPP and TID units on the thermal, photophysical and electrochemical properties of the polymers were investigated using thermogravimetric analysis, UV-vis-NIR absorption spectra, and cyclic voltammetry. Compared with the parent polymers (P1 and P2), the optical properties of the random terpolymers (P3–P6) were controlled successfully by tuning the ratio of DPP and TID. The increase in TID content induced an increased absorption between 450 and 600 nm and a lower highest occupied molecular orbital (HOMO) energy level, while higher DPP content resulted in stronger absorption between 600 and 900 nm. Bulk heterojunction solar cells based on the as-synthesized polymers as electron donors and (6,6)-phenyl-C-butyric acid methyl ester (PCBM) as the acceptor were fabricated. The best power conversion efficiency (PCE) of 5.62% was obtained from P5 (DPP:TID = 1:1) due to its high short-circuit current density (Jsc higher than 15 mA cm−2), mainly arising from the broadened light absorption. The results have demonstrated that the random terpolymers, with complementary light-absorption, have a great potential for increasing the photocurrent and PCE in polymer solar cells.
Co-reporter:Min Zhang, Zhencai Cao, Fen Wu, Huajie Chen, Meiqi Zhang, He Qiao, Songting Tan
European Polymer Journal 2014 Volume 57() pp:83-90
Publication Date(Web):August 2014
DOI:10.1016/j.eurpolymj.2014.05.011
•A novel terpolymer with DPP and TDTBT side chain was synthesized.•The absorption spectrum of the terpolymer was significantly broadened.•The HOMO energy level was down-shifted by introducing TDTBT side chain.•PSCs based on the terpolymer showed improved PCE as high as 4.85%.A new random terpolymer (PBDTT–DPP–TDTBT) based on alkylthienyl substituted benzodithiophene (BDTT), diketopyrrolopyrrole (DPP), and dialkylthienylbenzothiadiazole-thienyl vinylene (TDTBT) was designed and synthesized via the Stille coupling polymerization. The effects of DPP and TDTBT units on the thermal properties, photophysical and electrochemical properties of the polymer were investigated by thermogravimetric, UV–Vis–IR absorption spectra and cyclic voltammetry. By incorporating the TDTBT side-group into the random polymer main-chain, the absorption spectrum of PBDTT–DPP–TDTBT was broadened significantly. Moreover, the highest occupied molecular orbital (HOMO) energy level had been obviously lowered, consistent with the suitable backbone twists in main-chains. Therefore, the deep-lying HOMO energy level (ca. −5.5 eV) was achieved, which was beneficial for high open-circuit voltage (Voc). Bulk heterojunction solar cells based on as-synthesized polymer as electron donor and (6,6)-phenyl-C61-butyric acid methyl ester (PC61BM) as acceptor were fabricated. The results demonstrate that the terpolymer PBDTT–DPP–TDTBT exhibits an improved power conversion efficiency of 4.85%.
Co-reporter:Changwei Wang, Bin Zhao, Zhencai Cao, Ping Shen, Zhuo Tan, Xiangling Li and Songting Tan
Chemical Communications 2013 vol. 49(Issue 37) pp:3857-3859
Publication Date(Web):19 Mar 2013
DOI:10.1039/C3CC40620B
A novel conjugated side-chain polymer (PBDT-TID), based on benzo[1,2-b:4,5-b′]dithiophene (BDT) and isoindigo (ID) moieties, was designed and synthesized. The new polymer exhibited excellent microphase separation in active layers. Bulk heterojunction polymer solar cells fabricated from PBDT-TID and PC61BM showed promising power conversion efficiencies of 5.25% and 6.51% using conventional and inverted device structures, respectively.
Co-reporter:Xunshan Liu, Yuanshuai Huang, Zhencai Cao, Chao Weng, Huajie Chen and Songting Tan
Polymer Chemistry 2013 vol. 4(Issue 17) pp:4737-4745
Publication Date(Web):20 Jun 2013
DOI:10.1039/C3PY00614J
Two new copolymers (PT-Tz-DTBT and PT-Tz-DTffBT) of benzo[1,2-b:4,5-b′]dithiophene and thiazole (Tz) with different conjugated side groups 4,7-dithien-5-yl-2,1,3-benzodiathiazole (DTBT) and 5,6-difluoro-4,7-bis(4-hexylthiophen-2-yl)benzo[c][1,2,5]thiadiazole (DTffBT) were synthesized via the Stille coupling polymerization and developed for polymer solar cell applications. The thermal, photophysical, electrochemical and photovoltaic properties of the copolymers were investigated. The two copolymers exhibited relatively low HOMO energy levels of −5.58 eV for PT-Tz-DTBT and −5.59 eV for PT-Tz-DTffBT, respectively. Bulk heterojunction (BHJ) solar cells with two as-synthesized copolymers as electron donors and (6,6)-phenyl-C61-butyric acid methyl ester (PC61BM) as an electron acceptor exhibit power conversion efficiencies (PCEs) of 2.63% and 3.75% for PT-Tz-DTBT and PT-Tz-DTffBT, respectively. When PC71BM was used as an electron acceptor, a promising PCE of 3.65% and 4.42% for PT-Tz-DTffBT was achieved by using a conventional and inverted device structure, respectively.
Co-reporter:Changwei Wang, Zhencai Cao, Bin Zhao, Ping Shen, Xunshan Liu, Haohao Li, Tianpei Shen, Songting Tan
Dyes and Pigments 2013 Volume 98(Issue 3) pp:464-470
Publication Date(Web):September 2013
DOI:10.1016/j.dyepig.2013.03.011
•Three organic small molecules were synthesized and applied in BHJ solar cells.•The introduction of different terminal groups can tune the absorption spectra.•The organic molecule (TPA-DTBT) showed a power conversion efficiency of 1.85%.Three new organic small molecules (TPA-DTBT, TPA-DTBT-TH and TPA-DTBT-CAO) containing triphenylamine (TPA) and 4,7-bis(thiophen-2-yl)benzo[1,2,5]thiadiazole (DTBT) moieties with different terminal groups were designed and synthesized. Their thermal, photophysical, electrochemical and photovoltaic properties were investigated. The introduction of 2-ethylhexyl cyanoacetate and 2-tetradecyl thiophene as terminal groups extended molecular π-conjugation length and broadened the absorption spectra. Three small molecules exhibit good solubility in common organic solvents, good film-forming ability, and thermal stability. Bulk heterojunction (BHJ) solar cells based on the blend of small molecule TPA-DTBT and PC61BM showed a power conversion efficiency (η) of 1.85%.
Co-reporter:Changwei Wang, Yan Fang, Zhencai Cao, Hui Huang, Bin Zhao, Haohao Li, Ying Liu, Songting Tan
Dyes and Pigments 2013 Volume 97(Issue 3) pp:405-411
Publication Date(Web):June 2013
DOI:10.1016/j.dyepig.2013.01.009
Two novel branchlike organic dyes (WD1 and FD1) based on 4,7-bis-(4-hexylthiophen-2-yl)benzo[1,2,5]thiadiazole (DTBT) and triphenylamine, containing vinylenes and consecutive vinylenes as π-conjugated unit, respectively, were designed and synthesized for dye-sensitized solar cells (DSSCs). The photophysical, electrochemical and photovoltaic properties of the dyes were investigated. The introduction of consecutive vinylenes into two branches of the FD1 molecule leads to a remarkably red-shifted absorption and higher molar extinction coefficient compared with the reference dye D2. The DSSCs based on FD1 and WD1 dyes exhibited the power conversion efficiency of 7.04% and 2.18% under AM1.5G irradiation (100 mW/cm2).Highlights► Two branchlike organic dyes have been designed and synthesized. ► The introduction of consecutive vinylenes leads to high molar extinction coefficient. ► The DSSCs based on FD1 dye exhibited the maximum power conversion efficiency of 7.04%.
Co-reporter:Weiping Zhou, Zhencai Cao, Shenghui Jiang, Hongyan Huang, Lijun Deng, Yijiang Liu, Ping Shen, Bin Zhao, Songting Tan, Xianxi Zhang
Organic Electronics 2012 Volume 13(Issue 4) pp:560-569
Publication Date(Web):April 2012
DOI:10.1016/j.orgel.2011.12.014
Two novel porphyrin dyes (PMBTZ and PHBTZ) modified with alkyl-thiophene and 2,1,3-benzothiadiazole (BTZ) moieties were designed and synthesized. The optical and electrochemical properties were characterized by UV–visible, fluorescence spectroscopy and cyclic voltammetry. With the introduction of the low-band-gap chromophore onto the porphyrins, the absorption spectra of the two porphyrin dyes in the range of 450–600 nm were broadened and the maximum wavelength was red-shifted compared with PZn as expected. The first oxidation potentials (Eox1) were altered to the negative, which lowered from 1.27 to 1.11 and 1.15 eV, respectively. For a typical solar cell device based on dye PMBTZ, the maximal monochromatic incident photon-to-current conversion efficiency (IPCE) can reach to 65%, with a broad respondent region of 350–800 nm. Under standard global AM 1.5 solar condition, the dye-sensitized solar cell (DSSC) based on the dye PMBTZ showed the best photovoltaic performance: a short-circuit photocurrent density (Jsc) of 14.11 mA/cm2, an open-circuit photo voltage (Voc) of 0.59 V, and a fill factor (ff) of 0.66, corresponding to solar-to-electric power conversion efficiency (η) of 5.46%.Graphical abstractTwo novel porphyrin dyes linked the low-band-gap chromophore were designed and synthesized. The optical, electrochemical properties and photovoltaic performances were investigated in detail.Highlights► Two novel porphyrin dyes were designed and synthesized. ► The absorption spectra were broadened and the red-shifted due to introduce the low-band-gap chromophore. ► The dye-sensitized solar cell based on the dye PMBTZ obtained a solar-to-electric power conversion efficiency of 5.46%.
Co-reporter:Hongyan Huang, Zhencai Cao, Zhaojie Gu, Xinwei Li, Bin Zhao, Ping Shen, Songting Tan
European Polymer Journal 2012 Volume 48(Issue 10) pp:1805-1813
Publication Date(Web):October 2012
DOI:10.1016/j.eurpolymj.2012.06.016
Two phthalocyanine end-capped copolymers with conjugated dithienylbenzothiadiazole–vinylene side chains, PHY1 and PHY2, have been synthesized according to the Stille–Coupling polymerization method. The structures, thermostability, optical and electrochemical properties of the copolymers were characterized via NMR, GPC, TGA, DSC, UV–vis, photoluminescence (PL) spectroscopy, and cyclic voltammetry (CV), respectively. The two copolymers exhibit excellent film-forming ability and good thermostability in a wide temperature range. PHY1 and PHY2 end-capped with different phthalocyanines showed broad absorption bands ranging from the ultraviolet to the red/near-infrared (IR) region of the solar spectrum and deep HOMO energy levels. Bulk heterojunction polymer solar cells were fabricated based on PHY1 and PHY2 with [6,6]-phenyl-C61-butyric acid methyl ester (PC61BM) as the electron acceptor and showed power conversion efficiencies (PCE) of 1.56% and 1.26%, respectively, under the illumination of AM 1.5, 100 mW/100 cm2.Graphical abstractHighlights► Two novel phthalocyanine end-capped copolymers were synthesized and applied in PSCs. ► The soluble phthalocyanine derivatives were synthesized by employing the cheap materials. ► The copolymers show a broad absorption bands and a deep HOMO energy levels.
Co-reporter:Ying Liu, Xiaoyan Du, Zuo Xiao, Jiamin Cao, Songting Tan, Qiqun Zuo, Liming Ding
Synthetic Metals 2012 Volume 162(17–18) pp:1665-1671
Publication Date(Web):October 2012
DOI:10.1016/j.synthmet.2012.06.027
Three new low bandgap donor–acceptor–donor (D–A–D) type small molecules (M1–M3) containing naphthalene, thiophene, and diketopyrrolopyrrole were synthesized by Suzuki and Stille coupling reactions. The thermal, optical, electrochemical and photovoltaic properties of these molecules were investigated. These materials possess strong absorption at 475–750 nm and low-lying HOMO levels (−5.28 to −5.35 eV). Solution-processed bulk heterojunction solar cells based on M1–M3/PC71BM blends (1:1, w/w) demonstrate power conversion efficiencies (PCEs) as high as 2.59%, with a short-circuit current density (Jsc) of 6.83 mA/cm2, and an open-circuit voltage (Voc) of 0.88 V under AM1.5G irradiation (100 mW/cm2). Naphthalene-ended M1 and M3 show higher photovoltaic performance than M2 due to broad absorption and better morphology of the devices.Graphical abstractHighlights► Three new low bandgap donor–acceptor–donor type small molecules were developed. ► These molecules possess low-lying HOMO energy levels (−5.28 to −5.35 eV). ► Power conversion efficiencies of solar cells based on these molecules reaches 2.59%. ► Naphthalene-ended molecules show higher photovoltaic performance.
Co-reporter:Xia Guo;Haijun Fan;Maojie Zhang;Yu Huang;Yongfang Li
Journal of Applied Polymer Science 2012 Volume 124( Issue 1) pp:847-854
Publication Date(Web):
DOI:10.1002/app.35106
Abstract
Two poly(thiazole vinylene) derivatives, poly(4-hexylthiazole vinylene) (P4HTzV) and poly(4-nonylthiazole vinylene) (P4NTzV), were synthesized by Pd-catalyzed Stille coupling method. The polymers are soluble in common organic solvents such as o-dichlorobenzene and chloroform, and possess good thermal stability. P4HTzV and P4NTzV films exhibit broad absorption bands at 400–720 nm with an optical bandgap of 1.77 eV and 1.74 eV, respectively. The HOMO (the highest occupied molecular orbital) energy levels of P4HTzV and P4NTzV are −5.11 and −5.12 eV, respectively, measured by cyclic voltammetry. Preliminary results of the polymer solar cells based on P4HTzV : PC61BM ([6,6]-phenyl-C-61-butyric acid methyl ester) (1 : 1, w/w) show a power conversion efficiency of 0.21% with an open-circuit voltage of 0.55 V and a short circuit current density of 1.11 mA cm−2, under the illumination of AM1.5G, 100 mW cm−2. © 2011 Wiley Periodicals, Inc. J Appl Polym Sci, 2012
Co-reporter:Hongyan Huang, Zhencai Cao, Xiangling Li, Lingjun Zhang, Xunshan Liu, Huifang Zhao, Songting Tan
Synthetic Metals 2012 Volume 162(Issue 24) pp:2316-2321
Publication Date(Web):31 December 2012
DOI:10.1016/j.synthmet.2012.11.007
Two new soluble unsymmetrical zinc-phthalocyanine derivatives (PC-HY1, PC-HY2) with D-π-A structure bearing three tert-butylphenyl or tert-butylthienyl groups and cyanoacrylic acid groups were synthesized through a low-cost “anhydride” method. The photophysical, electrochemical and photovoltaic properties of the phthalocyanine derivatives were studied. The two phthalocyanine derivatives showed strong and broad absorption in the UV and red/near-infrared (IR) region, especially for PC-HY2. The electrochemical properties indicated that the two phthalocyanine derivatives are latent materials for dye-sensitized solar cells. Under the illumination of AM 1.5, 100 mW cm−2, dye-sensitized solar cells based on PC-HY1 and PC-HY2 showed power conversion efficiency (PCE) of 0.79% and 1.09%, respectively.Graphical abstractHighlights► Two new zinc-phthalocyanine dyes were synthesized through a low-cost “anhydrid” method. ► The chemical structures of two dyes were characterized. ► The zinc-phthalocyanine dyes were applied in PSCs.
Co-reporter:Zhaojie Gu;Lijun Deng;Hao Luo;Xia Guo;Haohao Li;Zhencai Cao;Xunshan Liu;Xinwei Li;Hongyan Huang;Yingzi Tan;Yong Pei
Journal of Polymer Science Part A: Polymer Chemistry 2012 Volume 50( Issue 18) pp:3848-3858
Publication Date(Web):
DOI:10.1002/pola.26180
Abstract
A series of novel low band gap polymers containing conjugated side chains with 4,7-dithien-5-yl-2,1,3-benzodiathiazole and different electron-withdrawing end groups of aldehyde (PT-DTBTCHO), 2-ethylhexyl cyanoacetate (PT-DTBTCN), 1,3-diethyl-2-thiobarbituric acid (PT-DTBTDT), and electron-donating end group of 2-methylthiophene (PT-DTBTMT) have been designed and synthesized. All polymers exhibit good solubility in common organic solvents, film-forming ability, and thermal stability. These conjugated polymers show the broad ultraviolet-visible absorption and the narrow optical band gaps in the range of 1.65–1.90 eV. Through changing the end group of conjugated side chains, the photophysical properties and energy levels of the polymers were tuned effectively. Bulk heterojunction solar cells based on the blend of these polymers and (6,6)-phenyl-C61-butyric acid methyl ester (PC61BM) reached the best power conversion efficiency (PCE) of 2.72%. © 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2012
Co-reporter:Lijun Deng, Zhaojie Gu, Zhencai Cao, Ping Shen, Xiangling Li, Lingjun Zhang, Songting Tan
Materials Science and Engineering: B 2012 Volume 177(Issue 18) pp:1641-1648
Publication Date(Web):1 November 2012
DOI:10.1016/j.mseb.2012.08.020
A novel asymmetrical D–A zinc porphyrin derivative with dimehtyl triphenylamine (donor unit) and methyl benzoate (acceptor unit) as para-arms was first synthesized. Then, two new copolymers (P1 and P2) containing D–A zinc porphyrin derivatives were synthesized by the Stille coupling method and applied in PSCs. Their structures, photophysical and electrochemical properties were characterized by 1H NMR, 13C NMR, gel permeation chromatography, thermogravimetric analysis, UV–vis absorption spectroscopy, photoluminescence spectroscopy, and cyclic voltammetry. The two copolymers exhibited good thermal stability and film-forming ability. The results showed that P1 containing D–A zinc porphyrin exhibits a strong absorption in the range of 400–500 nm. By the introduction of thiophene derivative with 4,7-di(4-hexylthiophen-2-yl)benzothiadiazole (T-DTBT) conjugated side-chain unit, P2 showed broader absorption in the region of 300–650 nm than P1. The photoluminescence spectra made clear that charge transfer between the whole main chain and side chain can be effective. Cyclic voltammograms revealed that the LUMO energy levels of P2 was reduced in comparison with P1 due to the introduction of electron-deficient T-DTBT conjugated side-chain unit, indicating that electron-injection and transporting properties have been improved. Polymer solar cells were fabricated based on the blend of the copolymers and methanofullerene[6,6]-phenyl C61-butyric acid methyl ester (PC61BM). The PSC based on P2:PC61BM (1:2, w/w) exhibited a power conversion efficiency of 1.26% under AM 1.5, 100 mW cm−2.Graphical abstractHighlights► A novel asymmetrical D–A zinc porphyrin derivative was first synthesized. ► Two copolymers containing D–A zinc porphyrin derivatives were synthesized. ► Polymer solar cells were fabricated and exhibited a maximal PCE of 1.26%.
Co-reporter:Yan Fang;Hui Huang;Peng Jiang;Haohao Li;Ping Shen
Journal of Materials Science 2012 Volume 47( Issue 15) pp:5706-5714
Publication Date(Web):2012 August
DOI:10.1007/s10853-012-6458-3
Three novel low-band gap phenylenevinylene copolymers (P1, P2, and P3), containing dihexylthienylbenzothiadiazole (DTBT) and triphenylamine (TPA) or tetraphenylbenzidine (TPD) were synthesized via the Wittig–Horner reaction. The effects of TPA and TPD on the thermal, optical, electrochemical and photovoltaic properties were investigated. The UV–Vis spectrum of P3, which contains TPD in the polymer backbone, exhibits a broader and stronger absorption in the film than those of P1 and P2. The bulk heterojunction solar cells were fabricated with the as-synthesized polymers as the donors and [6,6]-phenyl-C61-butyric acid methyl ester as the acceptor in a 1:4 weight ratio. The device based on P3 exhibits the maximum power conversion efficiency of 1.11 % under simulated AM 1.5 G solar irradiation (100 mW/cm2).
Co-reporter:Zhaojie Gu, Peng Tang, Bin Zhao, Hao Luo, Xia Guo, Huajie Chen, Gui Yu, Xinping Liu, Ping Shen, and Songting Tan
Macromolecules 2012 Volume 45(Issue 5) pp:2359-2366
Publication Date(Web):March 1, 2012
DOI:10.1021/ma202399n
Three novel copolymers (PT-ID, PT-DTBT, and PT-DTBTID) of benzo[1,2-b:4,5-b′]dithiophene and thiophene with different conjugated side groups (1,3-indanedione (ID), 4,7-dithien-5-yl-2,1,3-benzodiathiazole (DTBT), and DTBT-ID) were synthesized and developed for polymer solar cell applications. The effects of the different conjugated side groups on the thermal, photophysical, electrochemical and photovoltaic properties of these copolymers were investigated. As the length of the conjugated side groups increased, the absorption of the UV–vis region in solution was red-shifted. By changing the different side groups, the energy levels and band gaps of the resulted copolymers were effectively tuned. The three copolymers exhibit deep HOMO energy level and relatively high open-circuit voltage (Voc). Bulk heterojunction solar cells with these copolymers as electron donors and (6,6)-phenyl-C61-butyric acid methyl ester (PC61BM) as an electron acceptor exhibit power conversion efficiencies of 2.48%, 4.18% and 1.16% for PT-ID, PT-DTBT, and PT-DTBTID, respectively.
Co-reporter:Zhaojie Gu, Ping Shen, Sai-Wing Tsang, Ye Tao, Bin Zhao, Peng Tang, Yujuan Nie, Yan Fang and Songting Tan
Chemical Communications 2011 vol. 47(Issue 33) pp:9381-9383
Publication Date(Web):22 Jul 2011
DOI:10.1039/C1CC12851E
A new benzodithiophene-based copolymer PTG1 with dithienylbenzothiadiazole–vinylene side chains exhibits excellent film-forming ability, a deep HOMO energy level, and a good miscibility with PC71BM. Bulk heterojunction polymer solar cells fabricated from PTG1 and PC71BM showed a promising power conversion efficiency over 4.0%.
Co-reporter:Weiping Zhou, Bin Zhao, Ping Shen, Shenghui Jiang, Hongduan Huang, Lijun Deng, Songting Tan
Dyes and Pigments 2011 Volume 91(Issue 3) pp:404-412
Publication Date(Web):December 2011
DOI:10.1016/j.dyepig.2011.05.017
Four porphyrin dyes, incorporating multi-alkylthienyl appended porphyrins as the electron donor, the 2-cyanoacrylic acid as the electron acceptor, and different π-conjugated spacer, have been synthesized for dye-sensitized solar cells (DSSCs). All the porphyrin dyes studied in this work exhibit red-shifted and broadened electronic spectra respect to the reference PZn as expected. By the introduction of thienyl groups at the meso-positions, the energy level of Eox (excited-state oxidation potentials) is significantly shifted to the positive compared with the reference PZn, indicating a decreased HOMO–LUMO gap. The highest power conversion efficiency of the four dyes based on DSSCs reached 5.71% under AM 1.5 G irradiation.Highlights► The multi-alkylthienyl appended porphyrin dyes were synthesized and applied in DSSCs. ► All the porphyrin dyes exhibit red-shifted and broadened electronic spectra. ► The HOMO–LUMO energy gaps were decreased by the introduction of thienyl groups. ► The highest power conversion efficiency of the porphyrin dye reached 5.71%.
Co-reporter:Na Xiang, Xianwei Huang, Xiaoming Feng, Yijiang Liu, Bin Zhao, Lijun Deng, Ping Shen, Junjie Fei, Songting Tan
Dyes and Pigments 2011 Volume 88(Issue 1) pp:75-83
Publication Date(Web):January 2011
DOI:10.1016/j.dyepig.2010.05.003
Three donor–(π-spacer)–acceptor porphyrin dyes were synthesized for use in dye-sensitized solar cells. The dyes comprised the same donor (porphyrin derivative) and acceptor/anchoring group (2-cyanoacrylic acid) but varying π-spacer consisting of a combination of 4-methylthiophene, 4-hexylthiophene or 3,4-ethylenedioxythiophene groups. The dyes displayed different adsorption behavior and coverage of the TiO2 surface.
Co-reporter:Ping Shen, Yuhua Tang, Shenghui Jiang, Huajie Chen, Xiaoyan Zheng, Xueye Wang, Bin Zhao, Songting Tan
Organic Electronics 2011 Volume 12(Issue 1) pp:125-135
Publication Date(Web):January 2011
DOI:10.1016/j.orgel.2010.10.016
Three triphenylamine-based organic dyes SD6, SD7, and SD8 containing the bulky dual-role moieties (fluorene, carbazole, and spirobifluorene) in the molecular frameworks were synthesized, characterized and applied in dye-sensitized solar cells (DSSCs). The effects of dual-role moieties of organic dyes on their photophysical, electrochemical, and photovoltaic properties have been investigated in detail. These dyes exhibit strong charge transfer absorption bands in the visible region. Their redox potential levels were estimated by cyclic voltammetry and found to suit well to the charge flow in DSSCs. Inserting the dual-role moieties as the secondary donor between the triphenylamine and thiophene units increased the electron density of the donor groups, therefore reduced the HOMO–LUMO band gaps. The combination of ultraviolet–visible (UV–vis) region broad absorption bands with fairly high extinction coefficients and appropriate redox properties observed in these triphenylamine-based dyes make them promising dyes for DSSCs. For a typical solar cell device based on dye SD6, the maximal monochromatic incident photon-to-current conversion efficiency (IPCE) can reach to ∼73%, with a short-circuit photocurrent density (Jsc) of 14.25 mA/cm2, an open-circuit photovoltage (Voc) of 0.70 V, and a fill factor (FF) of 0.705, which corresponds to a power conversion efficiency (PCE) of 7.03%.Graphical abstractResearch highlightsThere are several advantages preformed by these D–D–π–A structural dyes: ► Enhanced light-harvesting ability and as a result of high short-circuit photocurrent density (Jsc). ► Lower-lying HOMO levels of the dyes, which are favorable for achieving high open-circuit voltage (Voc). ► Reduced dyes aggregates and effective retardation of charge recombination due to the extra hydrophobic alkyl chains of dual-role moieties incorporated with the long alkyl of thiophenyl unit.
Co-reporter:Shenghui Jiang, Ping Shen, Peng Jiang, Weiping Zhou, Bin Zhao, Yijiang Liu, Songting Tan
European Polymer Journal 2011 Volume 47(Issue 12) pp:2424-2431
Publication Date(Web):December 2011
DOI:10.1016/j.eurpolymj.2011.09.028
A novel phenylenevinylene copolymer (JP) with 4,7-dithien-5-yl-2,1,3-benzodiathiazole (DTBT) moiety along the backbone and di(p-tolyl)phenylamine (p-TPA) unit as side groups was synthesized and applied in polymer solar cells (PSCs). Introduction of DTBT and p-TPA moieties is beneficial to lowering the band gap, broadening the absorption spectrum and improving the photovoltaic properties of the copolymer. The effects of DTBT and p-TPA moieties on the thermal, photophysical, electrochemical and photovoltaic properties of the copolymer are investigated. The bulk heterojunction polymer solar cells based on JP and PC61BM (1:3, w/w) showed a maximum power conversion efficiency of 1.09% with an open-circuit voltage of 0.75 V, a short-circuit current of 3.69 mA cm−2, and a fill factor of 0.50.
Co-reporter:Tianpeng Ding;Bin Zhao;Ping Shen;Junjian Lu;Hui Li
Journal of Applied Polymer Science 2011 Volume 120( Issue 6) pp:3387-3394
Publication Date(Web):
DOI:10.1002/app.33294
Abstract
Two novel poly(p-phenylene vinylene) (PPV) derivatives with conjugated thiophene side chains, P1 and P2, were synthesized by Wittig-Horner reaction. The resulting polymers were characterized by 1H-NMR, FTIR, GPC, DSC, TGA, UV–Vis absorption spectroscopy and cyclic voltammetry (CV). The polymers exhibited good thermal stability and film-forming ability. The absorption spectra of P1 and P2 showed broader absorption band from 300 to 580 nm compared with poly[(p-phenylene vinylene)-alt-(2-methoxy-5-octyloxy-p-phenylene vinylene)] (P3) without conjugated thiophene side chains. Cyclic voltammograms displayed that the bandgap was reduced effectively by attaching conjugated thiophene side chains. This kind of polymer appears to be interesting candidates for solar-cell applications. © 2011 Wiley Periodicals, Inc. J Appl Polym Sci, 2011
Co-reporter:Weiping Zhou;Ping Shen;Bin Zhao;Peng Jiang;Lijun Deng
Journal of Polymer Science Part A: Polymer Chemistry 2011 Volume 49( Issue 12) pp:2685-2692
Publication Date(Web):
DOI:10.1002/pola.24700
Abstract
Two novel low band gap conjugated copolymers containing porphyrins, thiophenes, and 2,1,3-benzothiadiazole (BTZ) moieties were synthesized and applied in bulk heterojunction solar cells. The thermal, optical, electrochemical, and photovoltaic properties of the two copolymers were examined to investigate the effect of the introduction of BTZ moiety in the backbone of the porphyrin polymers. The copolymers exhibited good thermal stability and film-forming ability. The absorption spectra indicated that the BTZ moiety has significant influence on the UV–visible region spectra of the copolymers: with increasing the molar amount of BTZ moieties in conjugated main chain, the absorption in the range of 450–700 nm is largely broadened and red-shifted compared to the similar polymers without BTZ moiety, and the optical band gaps of copolymers were narrowed to ∼1.50 eV. The photoluminescence spectra showed that there is effective charge transfer in the whole conjugated main chain. Cyclic voltammetry displayed that the band gaps were reduced effectively by the introduction of the BTZ moieties. The bulk heterojunction solar cells were fabricated based on the blend of the copolymers and [6,6]-phenyl-C61-butyric acid methyl ester (PC61BM) in a 1:2 weight ratio. The maximum power conversion efficiency of 0.91% was obtained by using P2 as the electron donor under the illumination of AM 1.5, 100 mW/cm2. © 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2011
Co-reporter:Na Xiang, Weiping Zhou, Shenghui Jiang, Lijun Deng, Yijiang Liu, Zhuo Tan, Bin Zhao, Ping Shen, Songting Tan
Solar Energy Materials and Solar Cells 2011 95(4) pp: 1174-1181
Publication Date(Web):
DOI:10.1016/j.solmat.2010.12.051
Co-reporter:Yijiang Liu, Xia Guo, Na Xiang, Bin Zhao, Hui Huang, Hui Li, Ping Shen and Songting Tan
Journal of Materials Chemistry A 2010 vol. 20(Issue 6) pp:1140-1146
Publication Date(Web):15 Dec 2009
DOI:10.1039/B916935K
Two novel porphyrin-polythiophene star-shaped polymer (P-bs1 and P-bs2) containing triphenylamine terminated poly(3′-hexyl-2,2′-bithiophene) and poly(3′-hexyl-2,2′-bithiophene) as four arms in the peripheral of porphyrin core were synthesized by Stille reaction. The thermal, photophysical, electrochemical and photovoltaic properties of the porphyrin-polythiophene derivatives were investigated. The porphyrin-polythiophene derivatives showed broad absorption in the region of 350 ∼ 650 nm. In particular, the absorption intensity at 450 ∼ 650 nm was greatly enhanced for the meso-substituted polythiophene derivatives, P-bs2. The photoluminescence spectra indicated that the emission peaks of porphyrin units were suppressed by the intensive emission of thiophene units. The electrochemical properties indicated that the porphyrin-polythiophene derivatives are potential electron-donor materials for bulk heterojunction solar cells and dye-sensitized solar cells (DSSCs). Polymer bulk heterojunction solar cells based on P-bs2:PCBM (1:1, w/w) showed power conversion efficiencies (PCE) up to 0.61% under the illumination of AM 1.5, 100 mW cm−2, which increased by 69% compared to that of P-bs1 (0.36%). Meanwhile, higher PCE of 2.17% and 3.91% based on P-bs1 and P-bs2 polymer-sensitized solar cells were attained. The better photovoltaic properties benefited from longer arms of polythiophene derivatives.
Co-reporter:Huajie Chen, Hui Huang, Zongfang Tian, Ping Shen, Bin Zhao, Songting Tan
European Polymer Journal 2010 Volume 46(Issue 4) pp:673-680
Publication Date(Web):April 2010
DOI:10.1016/j.eurpolymj.2010.01.008
Three novel conjugated polymers (P1, P2, and P3), comprised of 2,5-dioctyloxy-1,4-phenylenevinylene and terthiophene derivatives with/without di(p-tolyl)phenylamine (TPAV) and oxadiazole (OXD) side groups, have been synthesized via the Witting–Horner reaction. The effect of TPAV and OXD side groups on the optical, electrochemical and photovoltaic properties has been investigated. It is found that the introduction of TPAV and OXD side groups to the backbone of P2 and P3 exhibits broader and stronger absorption than that of P1 without TPAV and OXD side groups. Photovoltaic cells have been fabricated with the as-synthesized polymers as the donors and [6,6]-phenyl-C61-butyric acid methyl ester (PCBM) as the acceptor in a 1:4 weight ratio. The device based on P2 shows a maximum power conversion efficiency of 1.75% under simulated AM 1.5 G solar irradiation (100 mW/cm2).
Co-reporter:Na Xiang, Yijiang Liu, Weiping Zhou, Hui Huang, Xia Guo, Zhuo Tan, Bin Zhao, Ping Shen, Songting Tan
European Polymer Journal 2010 Volume 46(Issue 5) pp:1084-1092
Publication Date(Web):May 2010
DOI:10.1016/j.eurpolymj.2010.01.015
Two novel conjugated polymers with alternating main chain structures of zinc porphyrin-terthiophene (P-PTT) and zinc porphyrin-oligothiophene (P-POT) were synthesized by Stille reaction. The effect of different lengths of thiophene chains on the thermal, optical, electrochemical, and photovoltaic properties of the two copolymers were investigated in detail. P-PTT exhibited higher onset decomposition temperature (392 °C) and glass-transition temperature (152 °C) than those of P-POT. The introduction of thiophene units in the meso-aryl positions of porphyrin resulted in the red shift and broader absorption spectrum compared with zinc porphyrin (PZn) monomer both in chloroform solutions and on thin solid films. The electrochemical properties indicated that the energy levels of the polymers were suitable for efficient charge transfer and separation at the interface between the polymer donor and PCBM acceptor. The bulk heterojunction solar cells based on P-PTT and P-POT showed power conversion efficiencies up to 0.32% and 0.18%, respectively.
Co-reporter:Yuhua Tang, Ping Shen, Tianpeng Ding, Hui Huang, Bin Zhao, Songting Tan
European Polymer Journal 2010 Volume 46(Issue 10) pp:2033-2041
Publication Date(Web):October 2010
DOI:10.1016/j.eurpolymj.2010.07.013
Three novel hyperbranched conjugated polymers (H-tpa, H-cya, and H-pca) with the same conjugated core structure and different functional terminal units were synthesized and applied in dye-sensitized solar cells (DSSCs) as photosensitizers. The photophysical, electrochemical and photovoltaic properties of the three hyperbranched conjugated polymers (HBPs) were investigated in detail. The results showed that donor-π-acceptor architecture in hyperbranched molecule benefited intramolecular charge transfer and consequently increased the generation of photocurrent. The three-dimensional (3D) steric configuration of HBPs could effectively suppress the aggregation of dyes on TiO2 film, which is beneficial for achieving good photovoltaic performances. Among the three hyperbranched dyes, the highest power conversion efficiency (η) of 3.93% (Jsc = 8.78 mA/cm2, Voc = 0.65 V, FF = 0.688) was obtained with a DSSC based on H-pca dye upon the addition of the same mass ratio chenodeoxycholic acid (CDCA) as coadsorbent under AM 1.5 irradiation with 100 mW/cm2 simulated sunlight.
Co-reporter:Meixiu Wan;Yingping Zou;Yongfang Li
Polymers for Advanced Technologies 2010 Volume 21( Issue 4) pp:256-262
Publication Date(Web):
DOI:10.1002/pat.1423
Abstract
Two alternative copolymers of thieno[3,4b]pyrazine (TPZ) and triphenylamine (TPA) or phenylene (Ph), P(TPA-TPZ) and P(Ph-TPZ), were synthesized by Wittig–Horner polycondensation and characterized by 1H NMR, elemental analysis, GPC, TGA, cyclic voltammetry, UV–Vis absorption, and photoluminescence (PL) spectroscopy. The polymers are soluble in common organic solvents and possess good thermal stability. Both of them shows strong solvatochromism phenomenon when dissolved in different solvents. The fluorescence of the copolymer solutions is efficiently quenched upon the addition of Hg2+, indicating that the two copolymers could be good Hg2+ detectors. More interestingly, the copolymers show high selectivity for the Hg2+ detection and P(TPA-TPZ) shows higher sensitivity and selectivity toward the Hg2+ detection than P(Ph-TPZ) does in the presence of other competing metal ions. The results imply that the conjugated polymers (CPs) containing the thieno[3,4b]pyrazine moiety are promising materials for chemosensors. Copyright © 2009 John Wiley & Sons, Ltd.
Co-reporter:Xianwei Huang, Ping Shen, Bin Zhao, Xiaoming Feng, Shenghui Jiang, Huajie Chen, Hui Li, Songting Tan
Solar Energy Materials and Solar Cells 2010 94(6) pp: 1005-1010
Publication Date(Web):
DOI:10.1016/j.solmat.2010.02.005
Co-reporter:Hui Li, Peng Jiang, Chenyi Yi, Chen Li, Shi-Xia Liu, Songting Tan, Bin Zhao, Jörg Braun, Wolfgang Meier, Thomas Wandlowski, and Silvio Decurtins
Macromolecules 2010 Volume 43(Issue 19) pp:8058-8062
Publication Date(Web):September 20, 2010
DOI:10.1021/ma101693d
Novel π-conjugated copolymers based on a soluble electroactive benzo[1,2-b:4,5-b′]difuran (BDF) chromophore have been synthesized by the introduction of thiophene/benzo[c][1,2,5]thiadiazole/9-phenylcarbazole comonomer units. These copolymers cover broad absorption ranges from 250 to 700 nm with narrow optical band gaps of 1.71−2.01 eV. Moreover, their band gaps as well as their molecular electronic energy levels are readily tuned by copolymerizing the BDF core with different π-conjugated electron-donating or withdrawing units in different ratios. Bulk heterojunction solar cell devices are fabricated using the copolymers as the electron donor and PCBM ([6,6]-phenyl-C61-butyric acid methyl ester) as the electron acceptor. Preliminary research has revealed power conversion efficiencies of 0.17−0.59% under AM 1.5 illumination (100 mW/cm2).
Co-reporter:Huajie Chen, Hui Huang, Xianwei Huang, John N. Clifford, Amparo Forneli, Emilio Palomares, Xiaoyan Zheng, Liping Zheng, Xianyou Wang, Ping Shen, Bin Zhao and Songting Tan
The Journal of Physical Chemistry C 2010 Volume 114(Issue 7) pp:3280-3286
Publication Date(Web):February 2, 2010
DOI:10.1021/jp911139x
Two novel branchlike organic dyes (D1 and D2) comprising two di(p-toyl)phenylamine moieties as the electron donor, cyanoacetic acid moieties as the electron acceptor, thiophene or 3-hexylthiophene moieties as the Π-spacer, were designed and synthesized for dye-sensitized solar cells (DSSCs). It was found that the introduction of two di(p-tolyl)phenylamine groups to form the branchlike configuration exhibited better photovoltaic performance due to the improvement of the electron donating and the light-harvesting properties. By the introduction of two di(p-tolyl)phenylamine groups into the framework of D2, it is interesting to note that the UV−vis absorption of D2 showed an obvious blue-shift but also improved molar extinction coefficient compared with that of D3. The transient absorption measurements showed that the dyes D1 and D2 with two di(p-tolyl)phenylamine-substitutes could effectively retard charge recombination between electrons at the TiO2 and the oxidized dyes. Among the three dyes studied, a maximum power conversion efficiency of 6.41% was obtained under simulated AM 1.5 G solar irradiation (100 mW/cm2) with a DSSC based on D2 dye (Jsc = 11.62 mA/cm2, Voc = 0.73 V, FF = 0.756) upon the addition of 1.0 × 10−3 M chenodeoxycholic acid (CDCA) as coadsorbent.
Co-reporter:Yijiang Liu, Na Xiang, Xiaoming Feng, Ping Shen, Weiping Zhou, Chao Weng, Bin Zhao and Songting Tan
Chemical Communications 2009 (Issue 18) pp:2499-2501
Publication Date(Web):30 Mar 2009
DOI:10.1039/B821985K
Three novel organic dyes based on porphyrin derivatives were designed and synthesized for dye-sensitized solar cells, resulting in a maximum power conversion efficiency (η) of 5.14% and a maximum IPCE value of 72% for a cell based on the PZnZn-hTdye.
Co-reporter:Ping Shen, Yijiang Liu, Xianwei Huang, Bin Zhao, Na Xiang, Junjie Fei, Liming Liu, Xueye Wang, Hui Huang, Songting Tan
Dyes and Pigments 2009 Volume 83(Issue 2) pp:187-197
Publication Date(Web):November 2009
DOI:10.1016/j.dyepig.2009.04.005
Several triphenylamine dyes, both with and without an n-hexyl-substituted oligothiophene as π-conjugated linker, were designed, synthesized and utilised in dye-sensitized, nanocrystalline, TiO2 solar cells. The effects of both the length of the π-conjugated unit and of the alkyl chain upon the photo-physical, electrochemical and photovoltaic properties of the dyes were studied. Between 1 and 3 thiophene units impart superior solar-to-electricity conversion efficiency and the hexyl chains also markedly improve both short-circuit photocurrent density and open-circuit photovoltage, which result in relatively high solar-to-electricity conversion efficiency. In EtOH solution, a dye-sensitized solar cell based on 2-cyano-3-(5-(4-(diphenylamino) phenyl)-4-hexylthiophenyl-2-yl) acrylic acid with one hexyl-substituted thiophene, π-conjugated unit, exhibited the largest observed maximum solar-to-electricity conversion efficiency of 7.26% under simulated AM 1.5 G solar irradiation (100 mW/cm2).
Co-reporter:Bin Zhao, Daxi Liu, Li Peng, Hui Li, Ping Shen, Na Xiang, Yijiang Liu, Songting Tan
European Polymer Journal 2009 Volume 45(Issue 7) pp:2079-2086
Publication Date(Web):July 2009
DOI:10.1016/j.eurpolymj.2009.03.018
Three soluble alternating conjugated copolymers, comprised of 9,9-dihexylfluorene and thiophene derivatives with/without oxadiazole side chains, were synthesized via the palladium-catalyzed Suzuki coupling reaction. The structures of the polymers were confirmed with 1H NMR and 13C NMR, and the effect of oxadiazole side chains on the thermal, optical, electrochemical and photovoltaic properties were investigated. The introduction of rigid oxadiazole side chains could benefit to improve thermal stabilities of the conjugated polymers. Cyclic voltammograms revealed that the LUMO energy levels of P2 and P3 were reduced in comparison with P1 due to the introduction of electron-deficient oxadiazole side chains, indicating that electron-injection and transporting properties have been improved. Photovoltaic cells (PVCs) were fabricated based on the blend of the as-synthesized copolymers and the fullerene acceptor [6,6]-phenyl-C61-butyric acid methyl ester (PCBM) in a 1:1 weight ratio. The maximum power conversion efficiency (PCE = 1.49%) was obtained for P3 as the electron donor under the illumination of AM 1.5, 100 mW/cm2.
Co-reporter:Ping Shen, Bin Zhao, Xianwei Huang, Hui Huang, Songting Tan
European Polymer Journal 2009 Volume 45(Issue 9) pp:2726-2731
Publication Date(Web):September 2009
DOI:10.1016/j.eurpolymj.2009.05.031
Two soluble poly(p-phenylenevinylene) derivatives (PPVs) with two bithiophenes as conjugated side chains, P1 and P2, were synthesized and characterized for application in polymer solar cells (PSCs). The thermal, photophysical, electrochemical and photovoltaic properties of the PPVs were investigated and compared with those of the PPVs without conjugated side chains. Bulk heterojunction solar cell devices are fabricated using the copolymers as the electron donor and PCBM ([6,6]-phenyl-C61-butyric acid methyl ester) as the electron acceptor. The power conversion efficiencies (η) based on the P1 and P2 are 1.1% and 1.41% under AM 1.5 illumination (100 mW/cm2), respectively.Two soluble poly(p-phenylenevinylene) derivatives (PPVs) with two bithiophenes as conjugated side chains, P1 and P2, were synthesized and characterized for application in polymer solar cells (PSCs). The power conversion efficiencies (η) based on the P1/P2 and PCBM are 1.1% and 1.41% under AM 1.5 illumination (100 mW/cm2), respectively.
Co-reporter:Meixiu Wan;Guangyi Sang;Yingping Zou;Yongfang Li
Journal of Applied Polymer Science 2009 Volume 113( Issue 3) pp:1415-1421
Publication Date(Web):
DOI:10.1002/app.29921
Abstract
A new polythiophene derivative with dioctyloxyl triphenylamine-vinylene (DOTPAV) conjugated side-chain, DOTPAV-PT, was synthesized by the Stille coupling method and characterized by 1H-NMR, 13C-NMR, elemental analysis, gel permeation chromatography, thermogravimetric analysis, UV–vis absorption spectroscopy, photoluminescence spectroscopy, and cyclic voltammetry. The polymer DOTPAV-PT is soluble in common organic solvents and possesses good thermal stability with 5% weight loss temperature of 310°C. The weight-average molecular weight of DOTPAV-PT is 8.0 K with a polydispersity index of 1.24. The hole mobility of the polymer determined from space-charge-limited current model was 1.25 × 10−4 cm2 V−1 s−1. The bulk heterojunction polymer solar cell with the configuration of ITO/PEDOT : PSS/polymer : PCBM (1 : 1)/Ca/Al was fabricated, and the power conversion efficiency of the device was 0.16% under the illumination of AM1.5, 100 mW cm−2. © 2009 Wiley Periodicals, Inc. J Appl Polym Sci, 2009
Co-reporter:Hui Li;Lei Wang;Bin Zhao;Ping Shen
Journal of Polymer Science Part A: Polymer Chemistry 2009 Volume 47( Issue 13) pp:3296-3308
Publication Date(Web):
DOI:10.1002/pola.23394
Abstract
A series of novel liquid-crystalline copolymers based on fluorene and triphenylamine-containing oligo(p-phenylenevinylene) derivatives have been synthesized according to the Suzuki polymerization method. The structures, optical and electrochemical properties of the copolymers were characterized by 1H NMR, 13C NMR, GPC, UV–vis, photoluminescence (PL) spectroscopy, and cyclic voltammetry (CV), respectively. The thermotropic phase behavior of the copolymers was investigated by using differential scanning calorimetry (DSC) and polarized optical microscope (POM). All of the copolymers exhibit thermally liquid crystalline properties and represent the characteristic Schlieren textures in a wide temperature range. The effects of the concentrations and chain length of the oligo(phenylenevinylene) units on the thermal properties, liquid crystalline, photo- and electroluminescent properties of the copolymers have been investigated in details. Among the copolymers-based devices with a configuration of ITO/PEDOT:PSS/polymers/Ca/Al, the device based on PF-LOPV05 exhibits the lowest turn-on voltage of 3 V and the maximum brightness of 210 cd/m2 at 8.3 V. A single layer device based on the blend of PF/PF-LOPV05 emits white electroluminescence with CIE coordinates of (0.30, 0.35) at 8 V. © 2009 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 47: 3296–3308, 2009
Co-reporter:Hui Li;Na Xiang;Lei Wang;Bin Zhao;Ping Shen;Junjian Lu
Journal of Polymer Science Part A: Polymer Chemistry 2009 Volume 47( Issue 20) pp:5291-5303
Publication Date(Web):
DOI:10.1002/pola.23578
Abstract
Two novel multicomponent copolymers (P1 and P2) containing polyfluorene (PF), oligo(phenylenevinylene) (OPV), and porphyrin (Por) derivatives were synthesized according to the Suzuki polymerization method. The structures, optical, and electrochemical properties of the two model compounds (OPV and Por) and multicomponent copolymers were characterized by 1H NMR, FTIR, elemental analysis, UV–vis spectroscopy, photoluminescence, and cyclic voltammetry, respectively. Both of the copolymers exhibit thermotropic liquid crystalline properties and represent the characteristic Schlieren textures in a wide temperature range. Electroluminescence spectra of these copolymers exhibit broadband emissions covering the entire visible region from 400 to 700 nm. The single layer polymer light emitting diodes device based on P2 with a configuration of indium tin oxide/poly(ethylenedioxythiophene):poly(styrenesulfonic acid)/polymers/Ca/Al emits white light with the Commission Internationale de l′Eclairage chromaticity coordinates of (0.29, 0.30), maximum brightness of 443 cd/m2. The white-light-emitting devices based on the novel multicomponent copolymers exhibit low turn-on voltage, and good color stability at different driving voltages as well. © 2009 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 47: 5291–5303, 2009
Co-reporter:Junjian Lu, Hui Li, Bing Yao, Bin Zhao, Chao Weng, Gangtie Lei, Ping Shen, Zhiyuan Xie and Songting Tan
The Journal of Physical Chemistry B 2009 Volume 113(Issue 13) pp:4203-4208
Publication Date(Web):March 4, 2009
DOI:10.1021/jp808740x
A series of block copolymers containing nonconjugated spacer and 3D π−π stacking structure with simultaneous blue-, green-, and yellow-emitting units has been synthesized and characterized. The dependence of the energy transfer and electroluminescence (EL) properties of these block copolymers on the contents of oligo(phenylenevinylene)s has been investigated. The block copolymer (GEO8-BEO-YEO4) with 98.8% blue-emitting oligomer (BEO), 0.8% green-emitting oligomer (GEO), and 0.4% yellow-emitting oligomer (YEO) showed the best electroluminescent performance, exhibiting a maximum luminance of 2309 cd/m2 and efficiency of 0.34 cd/A. The single-layer-polymer light-emitting diodes device based on GEO2-BEO-YEO4 emitted greenish white light with the CIE coordinates of (0.26, 0.37) at 10 V. The synergetic effect of the efficient energy transfer and 3D π−π stack of these block copolymers on the photoluminescent and electroluminescent properties are investigated.
Co-reporter:Junjian Lu, Ping Shen, Bin Zhao, Bing Yao, Zhiyuan Xie, Enhui Liu, Songting Tan
European Polymer Journal 2008 Volume 44(Issue 7) pp:2348-2355
Publication Date(Web):July 2008
DOI:10.1016/j.eurpolymj.2008.05.003
Two novel triphenylamine-substituted poly(p-phenylenevinylene) derivatives, P1 and P2, have been successfully synthesized through the Witting–Horner reaction. The structures and properties of the monomers and the resulting polymers were characterized by using 1H NMR, FT-IR, GPC, TGA, UV–vis absorption spectroscopy, cyclic voltammetry (CV) and electroluminescence (EL) spectroscopy. The obtained polymers exhibited good thermal stability and high photoluminescence quantum yield (0.42–0.90). The polymer light-emitting diodes (PLEDs) with the configuration of ITO/PEDOT/polymers/Ca/Al were fabricated. The single-layer device based on P1 and P2 emitted stable blue and yellow light with the turn-on voltage of 4 and 6 V, respectively. The maximum luminance of 3003 cd/m2 at 10 V was obtained for device P2.
Co-reporter:Songting Tan, Xiaoming Feng, Bin Zhao, Yingping Zou, Xianwei Huang
Materials Letters 2008 Volume 62(Issue 16) pp:2419-2421
Publication Date(Web):15 June 2008
DOI:10.1016/j.matlet.2007.12.036
This communication explores a facile approach for fabricating nanofibers containing luminescent conjugated polymer, poly(2-methoxy-5-octoxy)-1,4-phenylene vinylene)-alt-1,4-(phenylene vinylene) (PMO-PPV), and rare earth complex, Eu(ODBM)3phen (ODBM: 4-n-Octyloxydibenzoylmethanato; phen: 1,10-phenanthroline) via an electrospinning technique. The morphology and photoluminescent properties of the electrospun fibers were characterized by scanning electron microscopy, fluorescence spectrophotometer and UV optical microscopy. The electrospun fibers with diameters ranging from 70 nm to 200 nm as well as parallel orientation show strong green and red photoluminescence. This is the first but important approach towards novel applications of luminescent conjugated polymers and rare earth complex nanofibers. This kind of eletrospun nanofiber is a promising candidate for optical and electrical nanomaterials.
Co-reporter:Anying Xia, Zhuliang Yuan, Songting Tan, Yingping Zou, Zhanao Tan, Yi Yang, Yongfang Li
European Polymer Journal 2007 Volume 43(Issue 4) pp:1394-1401
Publication Date(Web):April 2007
DOI:10.1016/j.eurpolymj.2006.12.034
A series of alternating fluorene and p-phenylenevinylene copolymers containing non-conjugated spacer have been synthesized through the Wittig polycondensation reaction. These amorphous copolymers are highly soluble in common organic solvents and can be spin-cast to obtain transparent films. The effects of non-conjugated spacers in the main chain and the methoxyl groups on the side chain on the thermal behavior, photoluminescence (PL) and electroluminescence (EL) properties of these copolymers have been investigated in detail. Single-layered light-emitting diodes (LEDs) have been fabricated in the configuration of ITO/PEDOT/copolymer/Ca/Al and emitted blue light in the range of 456–492 nm. The measurements of current vs voltage show turn-on voltages at 6.2–12.4 V. Among the LEDs based on the six copolymers, the maximum EL brightness and efficiency of the LED based on P1 containing 4CH2 aliphatic segment length in the main chain and without methoxyl groups on side chain are reached 3936 cd/m2 and 0.70 cd/A, respectively.
Co-reporter:Songting Tan;Xianwei Huang;Bolin Wu
Polymer International 2007 Volume 56(Issue 11) pp:
Publication Date(Web):18 SEP 2007
DOI:10.1002/pi.2354
Electrospinning has the unique ability to produce ultrathin fibers from a rich variety of materials that include polymers, inorganic or organic compounds and blends. With the enormous increase of research interest in electrospun nanofibers, there is a strong need for a comprehensive review of electrospinning in a systematic fashion. This article presents some fascinating phenomena associated with the remarkable features of nanofibers in electrospinning processes and new progress in applications of electrospun nanofibers. Copyright © 2007 Society of Chemical Industry
Co-reporter:W. Zeng;S.T. Tan
Polymer Composites 2006 Volume 27(Issue 1) pp:24-29
Publication Date(Web):21 DEC 2005
DOI:10.1002/pc.20094
Electrically conductive composites were prepared using epoxy resin (EP) as matrix and nickel-coated polyethylene teraphthalate (PET) fibers as filler. The fibers were coated with nickel by plating and ultrasonic electroless deposition techniques. The coaxial transmission line method was used to measure the electromagnetic interference (EMI) shielding effectiveness of the nickel-coated PET fiber/EP composites. The contents of nickel and phosphorus in the coating were determined by X-ray photoelectron spectroscopy (XPS). As a result, the ultrasonic electroless nickel-coated PET fiber/EP composites showed excellent electrical conductive capability and better EMI shielding effectiveness due to higher content of nickel and lower content of phosphorus in the coating than conventional plated nickel-coated PET fiber/EP composites. POLYM. COMPOS., 27:24–29, 2006. © 2005 Society of Plastics Engineers
Co-reporter:Songting Tan, Yingping Zou, Weiguo Zhu, Changyun Jiang
Optical Materials 2006 Volume 28(8–9) pp:1108-1114
Publication Date(Web):June 2006
DOI:10.1016/j.optmat.2005.06.011
A series of asymmetrical alternating copoly(p-phenylenevinylene) derivatives (PPVs), poly(2-methoxy-5-alkoxy)-1,4-(phenylene vinylene)-alt-1,4-(phenylene vinylene), have been successfully synthesized via the Wittig polycondensation reaction as potential electroluminescent (EL) materials. These copolymers contain two components, one is phenylene vinylene with asymmetrical flexible side chain to improve the solubility of the copolymer in common solvents and to suppress its crystallization; the other is a rigid phenylene vinylene moiety to improve the luminescent quantum efficiency and the thermal stability. The photoluminescent (PL) properties and thermal behavior of these copolymers have been investigated in detail. The results showed that the PL intensity increased but the thermal stability decreased with increasing side chain length. A double-layer device of ITO/PEDOT–PSS/Polymer 3/Ba/Al showed a greenish yellow emission peaking at 548 nm with a turn-on voltage as low as 6.2 V. A maximum brightness of 534 cd/m2 was obtained at a driving voltage of 10 V.
Co-reporter:Song Ting Tan;Zeng Fang Huang;Min Na Liu;Xia Yu Wang
Journal of Applied Polymer Science 2006 Volume 99(Issue 3) pp:1269-1276
Publication Date(Web):18 NOV 2005
DOI:10.1002/app.22653
Curing kinetics of O-cresol formaldehyde epoxy resin and its blends with a liquid crystalline block copolymer (PDBH) cured with linear phenol–formaldehyde resin were studied by the nonisothermal differential scanning calorimetry (DSC) and isothermal DSC methods. The parameters of nonisothemal curing kinetics were obtained according to the Kissinger method, and those of isothermal curing kinetics were deduced on the basis of the n-order mechanism proposed by Kamal. The curing reaction is considered 1-order reaction as shown by the nonisothermal and isothermal results. The model gave a good description of curing kinetics up to the onset of vitrification. A diffusion factor has been introduced in the latter stage of reaction to describe the degree of conversion over the whole range. The obtained n-order model modified by diffusion-controlled factor is consistent with the experimental data almost over the whole range of conversion. © 2005 Wiley Periodicals, Inc. J Appl Polym Sci 99: 1269–1276, 2006
Co-reporter:Zeng Fang Huang;Song Ting Tan;Xia Yu Wang
Journal of Applied Polymer Science 2005 Volume 97(Issue 4) pp:1626-1631
Publication Date(Web):26 MAY 2005
DOI:10.1002/app.21885
Two novel liquid crystalline polymers, polydiethyleneglycol bis(4-hydroxybenzoate) terephthaloyl and block copolymer (PDBH), were synthesized by condensation reaction. The blends of the two liquid crystalline polymers and o-cresol formaldehyde epoxy resin were prepared by linear phenol-formaldehyde resin as curing reagent. Both mechanical and thermal properties of the blends containing liquid crystalline polymer were improved to a certain extent. By adding 5 wt % PDBH, the impact strength, bending strength, and the glass transition temperature were enhanced by 128%, 23.84%, and 28°C, respectively, compared with the unmodified version. The results of curing kinetics showed that the curing reaction active energy of the modified system by PDBH decreased from 79.70 to 70.26 kJ/mol. © 2005 Wiley Periodicals, Inc. J Appl Polym Sci 97: 1626–1631, 2005
Co-reporter:Song Ting Tan ;Joachim H. Wendorff ;Clemens Pietzonka;Zhi Hong Jia Dr.;Gui Qing Wang
ChemPhysChem 2005 Volume 6(Issue 8) pp:
Publication Date(Web):11 JUL 2005
DOI:10.1002/cphc.200500167
Superparamagnetic polymer nanofibers intended for drug delivery and therapy are considered here. Magnetite (Fe3O4) nanoparticles in the diameter range of 5–10 nm were synthesized in aqueous solution. Polymer nanofibers containing magnetite nanoparticles were prepared from commercially available poly(hydroxyethyl methacrylate), PHEMA, and poly-L-lactide (PLLA) by the electrospinning technique. Nanofibers with diameters ranging from 50 to 300 nm were obtained. Nanofibers containing up to 35 wt % magnetite nanoparticles displayed superparamagnetism at room temperature. The blocking temperature was about 50 K for an applied field of 500 Oe, and the saturation magnetization was 3.5 emu g−1and 1.1 emu g−1for Fe3O4/PHEMA and Fe3O4/PLLA nanofibers, respectively, and depended on the amount of Fe3O4 nanoparticles in the nanocomposites. To test such magnetic nano-objects for applications as drug carriers and drug-release systems we incorporated a fluorescent albumin with dog fluorescein isothiocyanate (ADFI).
Co-reporter:Changwei Wang, Bin Zhao, Zhencai Cao, Ping Shen, Zhuo Tan, Xiangling Li and Songting Tan
Chemical Communications 2013 - vol. 49(Issue 37) pp:NaN3859-3859
Publication Date(Web):2013/03/19
DOI:10.1039/C3CC40620B
A novel conjugated side-chain polymer (PBDT-TID), based on benzo[1,2-b:4,5-b′]dithiophene (BDT) and isoindigo (ID) moieties, was designed and synthesized. The new polymer exhibited excellent microphase separation in active layers. Bulk heterojunction polymer solar cells fabricated from PBDT-TID and PC61BM showed promising power conversion efficiencies of 5.25% and 6.51% using conventional and inverted device structures, respectively.
Co-reporter:Yijiang Liu, Na Xiang, Xiaoming Feng, Ping Shen, Weiping Zhou, Chao Weng, Bin Zhao and Songting Tan
Chemical Communications 2009(Issue 18) pp:NaN2501-2501
Publication Date(Web):2009/03/30
DOI:10.1039/B821985K
Three novel organic dyes based on porphyrin derivatives were designed and synthesized for dye-sensitized solar cells, resulting in a maximum power conversion efficiency (η) of 5.14% and a maximum IPCE value of 72% for a cell based on the PZnZn-hTdye.
Co-reporter:Zhaojie Gu, Ping Shen, Sai-Wing Tsang, Ye Tao, Bin Zhao, Peng Tang, Yujuan Nie, Yan Fang and Songting Tan
Chemical Communications 2011 - vol. 47(Issue 33) pp:NaN9383-9383
Publication Date(Web):2011/07/22
DOI:10.1039/C1CC12851E
A new benzodithiophene-based copolymer PTG1 with dithienylbenzothiadiazole–vinylene side chains exhibits excellent film-forming ability, a deep HOMO energy level, and a good miscibility with PC71BM. Bulk heterojunction polymer solar cells fabricated from PTG1 and PC71BM showed a promising power conversion efficiency over 4.0%.
Co-reporter:Yijiang Liu, Xia Guo, Na Xiang, Bin Zhao, Hui Huang, Hui Li, Ping Shen and Songting Tan
Journal of Materials Chemistry A 2010 - vol. 20(Issue 6) pp:NaN1146-1146
Publication Date(Web):2009/12/15
DOI:10.1039/B916935K
Two novel porphyrin-polythiophene star-shaped polymer (P-bs1 and P-bs2) containing triphenylamine terminated poly(3′-hexyl-2,2′-bithiophene) and poly(3′-hexyl-2,2′-bithiophene) as four arms in the peripheral of porphyrin core were synthesized by Stille reaction. The thermal, photophysical, electrochemical and photovoltaic properties of the porphyrin-polythiophene derivatives were investigated. The porphyrin-polythiophene derivatives showed broad absorption in the region of 350 ∼ 650 nm. In particular, the absorption intensity at 450 ∼ 650 nm was greatly enhanced for the meso-substituted polythiophene derivatives, P-bs2. The photoluminescence spectra indicated that the emission peaks of porphyrin units were suppressed by the intensive emission of thiophene units. The electrochemical properties indicated that the porphyrin-polythiophene derivatives are potential electron-donor materials for bulk heterojunction solar cells and dye-sensitized solar cells (DSSCs). Polymer bulk heterojunction solar cells based on P-bs2:PCBM (1:1, w/w) showed power conversion efficiencies (PCE) up to 0.61% under the illumination of AM 1.5, 100 mW cm−2, which increased by 69% compared to that of P-bs1 (0.36%). Meanwhile, higher PCE of 2.17% and 3.91% based on P-bs1 and P-bs2 polymer-sensitized solar cells were attained. The better photovoltaic properties benefited from longer arms of polythiophene derivatives.
Co-reporter:Yuanshuai Huang, Min Zhang, Huajie Chen, Fen Wu, Zhencai Cao, Lingjun Zhang and Songting Tan
Journal of Materials Chemistry A 2014 - vol. 2(Issue 15) pp:NaN5223-5223
Publication Date(Web):2014/01/21
DOI:10.1039/C4TA00020J
Three novel random conjugated terpolymers were designed and synthesized by copolymerizing a benzo[1,2-b:4,5-b′]dithiophene (BDT) donor with an electron-deficient diketopyrrolo[3,4-c]pyrrole (DPP) unit and a thiophene-vinylene-dithienyl-benzothiadiazole (TVDTBT) side group into a polymer backbone. By tuning the ratio of DPP and TVDTBT in the terpolymers, the optical properties and energy levels of these random terpolymers could be rationally controlled. As a result, the terpolymers exhibited a very broad absorption range of 300–900 nm with a high absorption coefficient and deep HOMO energy levels. Bulk heterojunction polymer solar cells fabricated from P3 and PC61BM exhibited a promising power conversion efficiency of 5.29% without any processing additives.
Co-reporter:Zhaokui Zeng, Zhiquan Zhang, Bin Zhao, Hailu Liu, Xiai Sun, Guo Wang, Jian Zhang and Songting Tan
Journal of Materials Chemistry A 2017 - vol. 5(Issue 16) pp:NaN7304-7304
Publication Date(Web):2017/03/21
DOI:10.1039/C7TA00495H
A copolymer with A–A structure is rationally designed and synthesized by using difluorobenzo[c]-cinnoline (DFBC) as weak electron-withdrawing (A) moieties and 1,4-diketo-pyrrolo[3,4-c]pyrrole (DPP) as strong A moieties. Polymer solar cells based on PDFBC-DPP and PC71BM showed a promising power conversion efficiency of 7.92%, which is one of the highest values in polymer solar cells based on A–A structure.
![Stannane, 1,1',1''-benzo[1,2-b:3,4-b':5,6-b'']trithiophene-2,5,8-triyltris[1,1,1-trimethyl-](/data/chemimg/2258800/1289556-30-4.png)
![Stannane, 1,1',1''-benzo[1,2-b:3,4-b':5,6-b'']trithiophene-2,5,8-triyltris[1,1,1-trimethyl-](/data/chemimg/2258800/1289556-30-4_b.png)
![Stannane, 1,1'-[[2,5-bis[(2-ethylhexyl)oxy]-1,4-phenylene]di-5,2-thiophenediyl]bis[1,1,1-trimethyl-](/data/chemimg/3782900/1820757-62-7.png)
![Stannane, 1,1'-[[2,5-bis[(2-ethylhexyl)oxy]-1,4-phenylene]di-5,2-thiophenediyl]bis[1,1,1-trimethyl-](/data/chemimg/3782900/1820757-62-7_b.png)
![8H-Indeno[2,1-b]thiophene, 8-(8H-indeno[2,1-b]thien-8-ylidene)-, (E)- (9CI)](/data/chemimg/3782900/38056-16-5.png)
![8H-Indeno[2,1-b]thiophene, 8-(8H-indeno[2,1-b]thien-8-ylidene)-, (E)- (9CI)](/data/chemimg/3782900/38056-16-5_b.png)
![Pyrrolo[3,4-c]pyrrole-1,4-dione, 2,5-bis(2-ethylhexyl)-3,6-bis(4-hexyl-2-thienyl)-2,5-dihydro-](/data/chemimg/3782900/1224430-41-4.png)
![Pyrrolo[3,4-c]pyrrole-1,4-dione, 2,5-bis(2-ethylhexyl)-3,6-bis(4-hexyl-2-thienyl)-2,5-dihydro-](/data/chemimg/3782900/1224430-41-4_b.png)
![Pyrrolo[3,4-c]pyrrole-1,4-dione, 3,6-bis(5-bromo-4-hexyl-2-thienyl)-2,5-bis(2-ethylhexyl)-2,5-dihydro-](/data/chemimg/3782900/1224430-42-5.png)
![Pyrrolo[3,4-c]pyrrole-1,4-dione, 3,6-bis(5-bromo-4-hexyl-2-thienyl)-2,5-bis(2-ethylhexyl)-2,5-dihydro-](/data/chemimg/3782900/1224430-42-5_b.png)
![Phosphonic acid, P-[(4,7-dibromo-2,1,3-benzothiadiazol-5-yl)methyl]-, diethyl ester](/data/chemimg/3782900/1426326-74-0.png)
![Phosphonic acid, P-[(4,7-dibromo-2,1,3-benzothiadiazol-5-yl)methyl]-, diethyl ester](/data/chemimg/3782900/1426326-74-0_b.png)
![8H-Indeno[2,1-b]thiophene, 2-bromo-8-(2-bromo-8H-indeno[2,1-b]thien-8-ylidene)-, (8E)-](/data/chemimg/3782900/1597464-91-9.png)
![8H-Indeno[2,1-b]thiophene, 2-bromo-8-(2-bromo-8H-indeno[2,1-b]thien-8-ylidene)-, (8E)-](/data/chemimg/3782900/1597464-91-9_b.png)
![Stannane, trimethyl[(8E)-8-[2-(trimethylstannyl)-8H-indeno[2,1-b]thien-8-ylidene]-8H-indeno[2,1-b]thien-2-yl]-](/data/chemimg/3782900/1597464-92-0.png)
![Stannane, trimethyl[(8E)-8-[2-(trimethylstannyl)-8H-indeno[2,1-b]thien-8-ylidene]-8H-indeno[2,1-b]thien-2-yl]-](/data/chemimg/3782900/1597464-92-0_b.png)
![2,1,3-Benzothiadiazole, 5,6-difluoro-4,7-bis[5-(trimethylstannyl)selenophene-2-yl]-](/data/chemimg/3782900/1772705-19-7.png)
![2,1,3-Benzothiadiazole, 5,6-difluoro-4,7-bis[5-(trimethylstannyl)selenophene-2-yl]-](/data/chemimg/3782900/1772705-19-7_b.png)
![4H-Indeno[1,2-b]thiophen-6-amine, N,N,4,4-tetrakis(4-methylphenyl)-](/data/chemimg/3782900/1859128-15-6.png)
![4H-Indeno[1,2-b]thiophen-6-amine, N,N,4,4-tetrakis(4-methylphenyl)-](/data/chemimg/3782900/1859128-15-6_b.png)
![Pyrrolo[3,4-c]pyrrole-1,4-dione, 3,6-bis(4-hexyl-2-thienyl)-2,5-dihydro-](/data/chemimg/3782900/1224430-40-3.png)
![Pyrrolo[3,4-c]pyrrole-1,4-dione, 3,6-bis(4-hexyl-2-thienyl)-2,5-dihydro-](/data/chemimg/3782900/1224430-40-3_b.png)
![Benzo[1,2-b:4,5-b']dithiophene, 4,8-bis[(2-ethylhexyl)thio]-](/data/chemimg/3782900/1350448-76-8.png)
![Benzo[1,2-b:4,5-b']dithiophene, 4,8-bis[(2-ethylhexyl)thio]-](/data/chemimg/3782900/1350448-76-8_b.png)
![Thieno[3,2-b]thiophene, 3-heptyl-](/data/chemimg/3782900/1714089-79-8.png)
![Thieno[3,2-b]thiophene, 3-heptyl-](/data/chemimg/3782900/1714089-79-8_b.png)
![Stannane, tributyl[5-(2-octyldodecyl)-2-thienyl]-](/data/chemimg/3782900/1808173-74-1.png)
![Stannane, tributyl[5-(2-octyldodecyl)-2-thienyl]-](/data/chemimg/3782900/1808173-74-1_b.png)
![Benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetrone, 4,9-dibromo-2,7-bis(2-octyldodecyl)-, polymer with 2,5-bis[5-(trimethylstannyl)-2-thienyl]-1,3,4-oxadiazole](/data/chemimg/3782900/2065217-88-9.png)
![Benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetrone, 4,9-dibromo-2,7-bis(2-octyldodecyl)-, polymer with 2,5-bis[5-(trimethylstannyl)-2-thienyl]-1,3,4-oxadiazole](/data/chemimg/3782900/2065217-88-9_b.png)
![Benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetrone, 4,9-dibromo-2,7-bis(2-octyldodecyl)-, polymer with 2,5-bis[5-(trimethylstannyl)-2-thienyl]-1,3,4-thiadiazole](/data/chemimg/3782900/2065217-89-0.png)
![Benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetrone, 4,9-dibromo-2,7-bis(2-octyldodecyl)-, polymer with 2,5-bis[5-(trimethylstannyl)-2-thienyl]-1,3,4-thiadiazole](/data/chemimg/3782900/2065217-89-0_b.png)
![Thieno[3,2-b]thiophene-2-carboxylic acid, 3-methyl-, methyl ester](/data/chemimg/3782900/20969-42-0.png)
![Thieno[3,2-b]thiophene-2-carboxylic acid, 3-methyl-, methyl ester](/data/chemimg/3782900/20969-42-0_b.png)
![Benzo[1,2-b:3,4-b':5,6-b'']trithiophene, 2-octyl-](/data/chemimg/3782900/1227939-53-8.png)
![Benzo[1,2-b:3,4-b':5,6-b'']trithiophene, 2-octyl-](/data/chemimg/3782900/1227939-53-8_b.png)
![1-Octanone, 1-benzo[1,2-b:3,4-b':5,6-b'']trithien-2-yl-](/data/chemimg/3782900/1227939-56-1.png)
![1-Octanone, 1-benzo[1,2-b:3,4-b':5,6-b'']trithien-2-yl-](/data/chemimg/3782900/1227939-56-1_b.png)
![2-Thiophenecarboxaldehyde, 5-[(1E)-2-(2,5-dibromo-3-thienyl)ethenyl]-](/data/chemimg/3782900/1325629-80-8.png)
![2-Thiophenecarboxaldehyde, 5-[(1E)-2-(2,5-dibromo-3-thienyl)ethenyl]-](/data/chemimg/3782900/1325629-80-8_b.png)
![3-Thiophenecarboxaldehyde, 2,5-dibromo-, polymer with 1,1'-[4,8-bis[(2-ethylhexyl)oxy]benzo[1,2-b:4,5-b']dithiophene-2,6-diyl]bis[1,1,1-trimethylstannane]](/data/chemimg/3782900/1361514-74-0.png)
![3-Thiophenecarboxaldehyde, 2,5-dibromo-, polymer with 1,1'-[4,8-bis[(2-ethylhexyl)oxy]benzo[1,2-b:4,5-b']dithiophene-2,6-diyl]bis[1,1,1-trimethylstannane]](/data/chemimg/3782900/1361514-74-0_b.png)
![Poly[[2,5-bis(2-ethylhexyl)-2,3,5,6-tetrahydro-3,6-dioxopyrrolo[3,4-c]pyrrole-1,4-diyl]-2,5-thiophenediyl[4,8-bis[5-(2-ethylhexyl)-2-thienyl]benzo[1,2-b:4,5-b']dithiophene-2,6-diyl]-2,5-thiophenediyl]](/data/chemimg/3731500/1404095-90-4.png)
![Poly[[2,5-bis(2-ethylhexyl)-2,3,5,6-tetrahydro-3,6-dioxopyrrolo[3,4-c]pyrrole-1,4-diyl]-2,5-thiophenediyl[4,8-bis[5-(2-ethylhexyl)-2-thienyl]benzo[1,2-b:4,5-b']dithiophene-2,6-diyl]-2,5-thiophenediyl]](/data/chemimg/3731500/1404095-90-4_b.png)
![2H-Indol-2-one, 6-[5-[2-(2,5-dibromo-3-thienyl)ethenyl]-2-thienyl]-1-(2-ethylhexyl)-3-[1-(2-ethylhexyl)-1,2-dihydro-2-oxo-3H-indol-3-ylidene]-1,3-dihydro-](/data/chemimg/3782900/1430806-40-8.png)
![2H-Indol-2-one, 6-[5-[2-(2,5-dibromo-3-thienyl)ethenyl]-2-thienyl]-1-(2-ethylhexyl)-3-[1-(2-ethylhexyl)-1,2-dihydro-2-oxo-3H-indol-3-ylidene]-1,3-dihydro-](/data/chemimg/3782900/1430806-40-8_b.png)
![[2,2':5',2''-Terthiophene]-3'-carboxaldehyde, 4,4''-dihexyl-](/data/chemimg/3782900/1448326-72-4.png)
![[2,2':5',2''-Terthiophene]-3'-carboxaldehyde, 4,4''-dihexyl-](/data/chemimg/3782900/1448326-72-4_b.png)
![2-Thiophenecarboxaldehyde, 5-[5,6-difluoro-7-(4-hexyl-2-thienyl)-2,1,3-benzothiadiazol-4-yl]-3-hexyl-](/data/chemimg/3782900/1616347-76-2.png)
![2-Thiophenecarboxaldehyde, 5-[5,6-difluoro-7-(4-hexyl-2-thienyl)-2,1,3-benzothiadiazol-4-yl]-3-hexyl-](/data/chemimg/3782900/1616347-76-2_b.png)
![2-Thiophenecarboxaldehyde, 5-[10-(2-ethylhexyl)-10H-phenoxazin-3-yl]-](/data/chemimg/3782900/1620788-62-6.png)
![2-Thiophenecarboxaldehyde, 5-[10-(2-ethylhexyl)-10H-phenoxazin-3-yl]-](/data/chemimg/3782900/1620788-62-6_b.png)
![[2,2'-Bithiophene]-5-carboxaldehyde, 5'-bromo-3-hexyl-](/data/chemimg/3782900/1664338-28-6.png)
![[2,2'-Bithiophene]-5-carboxaldehyde, 5'-bromo-3-hexyl-](/data/chemimg/3782900/1664338-28-6_b.png)
![3-Thiophenecarboxylic acid, 2-[4-[bis(4-methylphenyl)amino]phenyl]-, methyl ester](/data/chemimg/3782900/1859128-14-5.png)
![3-Thiophenecarboxylic acid, 2-[4-[bis(4-methylphenyl)amino]phenyl]-, methyl ester](/data/chemimg/3782900/1859128-14-5_b.png)
![Benzoic acid, 4-[7-[6-[bis(4-methylphenyl)amino]-4,4-bis(4-methylphenyl)-4H-indeno[1,2-b]thien-2-yl]-2,1,3-benzothiadiazol-4-yl]-, methyl ester](/data/chemimg/3782800/1859128-17-8.png)
![Benzoic acid, 4-[7-[6-[bis(4-methylphenyl)amino]-4,4-bis(4-methylphenyl)-4H-indeno[1,2-b]thien-2-yl]-2,1,3-benzothiadiazol-4-yl]-, methyl ester](/data/chemimg/3782800/1859128-17-8_b.png)
![Benzoic acid, 4-[7-[6-[bis(4-methylphenyl)amino]-4,4-bis(4-methylphenyl)-4H-indeno[1,2-b]thien-2-yl]-2,1,3-benzothiadiazol-4-yl]-](/data/chemimg/3782800/1859128-18-9.png)
![Benzoic acid, 4-[7-[6-[bis(4-methylphenyl)amino]-4,4-bis(4-methylphenyl)-4H-indeno[1,2-b]thien-2-yl]-2,1,3-benzothiadiazol-4-yl]-](/data/chemimg/3782800/1859128-18-9_b.png)
![Benzoic acid, 4-[7-[6-[bis(4-methylphenyl)amino]-4,4-bis(4-methylphenyl)-4H-indeno[1,2-b]thien-2-yl]-5,6-difluoro-2,1,3-benzothiadiazol-4-yl]-, methyl ester](/data/chemimg/3782800/1859128-20-3.png)
![Benzoic acid, 4-[7-[6-[bis(4-methylphenyl)amino]-4,4-bis(4-methylphenyl)-4H-indeno[1,2-b]thien-2-yl]-5,6-difluoro-2,1,3-benzothiadiazol-4-yl]-, methyl ester](/data/chemimg/3782800/1859128-20-3_b.png)
![Benzoic acid, 4-[7-[6-[bis(4-methylphenyl)amino]-4,4-bis(4-methylphenyl)-4H-indeno[1,2-b]thien-2-yl]-5,6-difluoro-2,1,3-benzothiadiazol-4-yl]-](/data/chemimg/3782800/1859128-21-4.png)
![Benzoic acid, 4-[7-[6-[bis(4-methylphenyl)amino]-4,4-bis(4-methylphenyl)-4H-indeno[1,2-b]thien-2-yl]-5,6-difluoro-2,1,3-benzothiadiazol-4-yl]-](/data/chemimg/3782800/1859128-21-4_b.png)
![2,1,3-Benzothiadiazole, 4,7-bis[5-(trimethylstannyl)selenophene-2-yl]-](/data/chemimg/3782800/1988691-50-4.png)
![2,1,3-Benzothiadiazole, 4,7-bis[5-(trimethylstannyl)selenophene-2-yl]-](/data/chemimg/3782800/1988691-50-4_b.png)
![4H-Indeno[1,2-b]thiophen-6-amine, N,N,4,4-tetrakis(4-methylphenyl)-2-(trimethylstannyl)-](/data/chemimg/3782800/2056254-75-0.png)
![4H-Indeno[1,2-b]thiophen-6-amine, N,N,4,4-tetrakis(4-methylphenyl)-2-(trimethylstannyl)-](/data/chemimg/3782800/2056254-75-0_b.png)
![1,3,4-Oxadiazole, 2,5-bis[5-(trimethylstannyl)-2-thienyl]-](/data/chemimg/3782800/2065217-86-7.png)
![1,3,4-Oxadiazole, 2,5-bis[5-(trimethylstannyl)-2-thienyl]-](/data/chemimg/3782800/2065217-86-7_b.png)
![1,3,4-Thiadiazole, 2,5-bis[5-(trimethylstannyl)-2-thienyl]-](/data/chemimg/3782800/2065217-87-8.png)
![1,3,4-Thiadiazole, 2,5-bis[5-(trimethylstannyl)-2-thienyl]-](/data/chemimg/3782800/2065217-87-8_b.png)
![Benzoic acid, 4-[5-[4-(5-bromo-2-thienyl)-2,5-bis(2-ethylhexyl)-2,3,5,6-tetrahydro-3,6-dioxopyrrolo[3,4-c]pyrrol-1-yl]-2-thienyl]-, methyl ester](/data/chemimg/3777600/2080446-93-9.png)
![Benzoic acid, 4-[5-[4-(5-bromo-2-thienyl)-2,5-bis(2-ethylhexyl)-2,3,5,6-tetrahydro-3,6-dioxopyrrolo[3,4-c]pyrrol-1-yl]-2-thienyl]-, methyl ester](/data/chemimg/3777600/2080446-93-9_b.png)
![Benzo[c]cinnoline, 3,8-bis[5-bromo-4-(2-hexyldecyl)-2-thienyl]-2,9-difluoro-](/data/chemimg/3782800/2098478-98-7.png)
![Benzo[c]cinnoline, 3,8-bis[5-bromo-4-(2-hexyldecyl)-2-thienyl]-2,9-difluoro-](/data/chemimg/3782800/2098478-98-7_b.png)
![2,1,3-Benzothiadiazole, 4-[5-[2-(2,5-dibromo-3-thienyl)ethenyl]-4-hexyl-2-thienyl]-5,6-difluoro-7-(4-hexyl-2-thienyl)-](/data/chemimg/3782800/1644454-21-6.png)
![2,1,3-Benzothiadiazole, 4-[5-[2-(2,5-dibromo-3-thienyl)ethenyl]-4-hexyl-2-thienyl]-5,6-difluoro-7-(4-hexyl-2-thienyl)-](/data/chemimg/3782800/1644454-21-6_b.png)
![2,1,3-Benzothiadiazole, 4-[5-[2-(2,5-dibromo-3-thienyl)ethenyl]-4-hexyl-2-thienyl]-5,6-difluoro-7-(4-hexyl-2-thienyl)-, polymer with 1,1'-[4,8-bis[(2-ethylhexyl)thio]benzo[1,2-b:4,5-b']dithiophene-2,6-diyl]bis[1,1,1-trimethylstannane]](/data/chemimg/3782800/1644454-22-7.png)
![2,1,3-Benzothiadiazole, 4-[5-[2-(2,5-dibromo-3-thienyl)ethenyl]-4-hexyl-2-thienyl]-5,6-difluoro-7-(4-hexyl-2-thienyl)-, polymer with 1,1'-[4,8-bis[(2-ethylhexyl)thio]benzo[1,2-b:4,5-b']dithiophene-2,6-diyl]bis[1,1,1-trimethylstannane]](/data/chemimg/3782800/1644454-22-7_b.png)
![2H-Indol-2-one, 6-[5-[2-(2,5-dibromo-3-thienyl)ethenyl]-2-thienyl]-1-(2-ethylhexyl)-3-[1-(2-ethylhexyl)-1,2-dihydro-2-oxo-3H-indol-3-ylidene]-1,3-dihydro-, polymer with 1,1'-[4,8-bis[(2-ethylhexyl)thio]benzo[1,2-b:4,5-b']dithiophene-2,6-diyl]bis[1,1,1-trimethylstannane]](/data/chemimg/3782800/1644454-24-9.png)
![2H-Indol-2-one, 6-[5-[2-(2,5-dibromo-3-thienyl)ethenyl]-2-thienyl]-1-(2-ethylhexyl)-3-[1-(2-ethylhexyl)-1,2-dihydro-2-oxo-3H-indol-3-ylidene]-1,3-dihydro-, polymer with 1,1'-[4,8-bis[(2-ethylhexyl)thio]benzo[1,2-b:4,5-b']dithiophene-2,6-diyl]bis[1,1,1-trimethylstannane]](/data/chemimg/3782800/1644454-24-9_b.png)
![2H-Indol-2-one, 6-bromo-3-[6-bromo-1,2-dihydro-1-(2-octyldodecyl)-2-oxo-3H-indol-3-ylidene]-1,3-dihydro-1-(2-octyldodecyl)-, polymer with trimethyl[(8E)-8-[2-(trimethylstannyl)-8H-indeno[2,1-b]thien-8-ylidene]-8H-indeno[2,1-b]thien-2-yl]stannane](/data/chemimg/3782800/1690338-98-7.png)
![2H-Indol-2-one, 6-bromo-3-[6-bromo-1,2-dihydro-1-(2-octyldodecyl)-2-oxo-3H-indol-3-ylidene]-1,3-dihydro-1-(2-octyldodecyl)-, polymer with trimethyl[(8E)-8-[2-(trimethylstannyl)-8H-indeno[2,1-b]thien-8-ylidene]-8H-indeno[2,1-b]thien-2-yl]stannane](/data/chemimg/3782800/1690338-98-7_b.png)
![Pyrrolo[3,4-c]pyrrole-1,4-dione, 3,6-bis(5-bromo-2-thienyl)-2,5-dihydro-2,5-bis(2-octyldodecyl)-, polymer with trimethyl[(8E)-8-[2-(trimethylstannyl)-8H-indeno[2,1-b]thien-8-ylidene]-8H-indeno[2,1-b]thien-2-yl]stannane](/data/chemimg/3782800/1690339-00-4.png)
![Pyrrolo[3,4-c]pyrrole-1,4-dione, 3,6-bis(5-bromo-2-thienyl)-2,5-dihydro-2,5-bis(2-octyldodecyl)-, polymer with trimethyl[(8E)-8-[2-(trimethylstannyl)-8H-indeno[2,1-b]thien-8-ylidene]-8H-indeno[2,1-b]thien-2-yl]stannane](/data/chemimg/3782800/1690339-00-4_b.png)
![Benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetrone, 4,9-bis(5-bromo-2-thienyl)-2,7-bis(2-octyldodecyl)-, polymer with trimethyl[(8E)-8-[2-(trimethylstannyl)-8H-indeno[2,1-b]thien-8-ylidene]-8H-indeno[2,1-b]thien-2-yl]stannane](/data/chemimg/3782800/1690339-02-6.png)
![Benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetrone, 4,9-bis(5-bromo-2-thienyl)-2,7-bis(2-octyldodecyl)-, polymer with trimethyl[(8E)-8-[2-(trimethylstannyl)-8H-indeno[2,1-b]thien-8-ylidene]-8H-indeno[2,1-b]thien-2-yl]stannane](/data/chemimg/3782800/1690339-02-6_b.png)
![[2,2':5',2''-Terthiophene]-3'-carboxaldehyde, 5,5''-dibromo-4,4''-dihexyl-](/data/chemimg/3782800/1695575-66-6.png)
![[2,2':5',2''-Terthiophene]-3'-carboxaldehyde, 5,5''-dibromo-4,4''-dihexyl-](/data/chemimg/3782800/1695575-66-6_b.png)
![2-Thiophenecarboxaldehyde, 5-[(1E)-2-(5,5''-dibromo-4,4''-dihexyl[2,2':5',2''-terthiophen]-3'-yl)ethenyl]-](/data/chemimg/3782800/1695575-68-8.png)
![2-Thiophenecarboxaldehyde, 5-[(1E)-2-(5,5''-dibromo-4,4''-dihexyl[2,2':5',2''-terthiophen]-3'-yl)ethenyl]-](/data/chemimg/3782800/1695575-68-8_b.png)
![[2,2':5',2''-Terthiophene]-3'-carboxaldehyde, 5,5''-dibromo-4,4''-dihexyl-, polymer with 1,1'-[4,8-bis[(2-ethylhexyl)oxy]benzo[1,2-b:4,5-b']dithiophene-2,6-diyl]bis[1,1,1-trimethylstannane]](/data/chemimg/3782800/1695575-69-9.png)
![[2,2':5',2''-Terthiophene]-3'-carboxaldehyde, 5,5''-dibromo-4,4''-dihexyl-, polymer with 1,1'-[4,8-bis[(2-ethylhexyl)oxy]benzo[1,2-b:4,5-b']dithiophene-2,6-diyl]bis[1,1,1-trimethylstannane]](/data/chemimg/3782800/1695575-69-9_b.png)
![2-Thiophenecarboxaldehyde, 5-[(1E)-2-(2,5-dibromo-3-thienyl)ethenyl]-, polymer with 1,1'-[4,8-bis[(2-ethylhexyl)oxy]benzo[1,2-b:4,5-b']dithiophene-2,6-diyl]bis[1,1,1-trimethylstannane]](/data/chemimg/3782800/1695575-70-2.png)
![2-Thiophenecarboxaldehyde, 5-[(1E)-2-(2,5-dibromo-3-thienyl)ethenyl]-, polymer with 1,1'-[4,8-bis[(2-ethylhexyl)oxy]benzo[1,2-b:4,5-b']dithiophene-2,6-diyl]bis[1,1,1-trimethylstannane]](/data/chemimg/3782800/1695575-70-2_b.png)
![2-Thiophenecarboxaldehyde, 5-[(1E)-2-(5,5''-dibromo-4,4''-dihexyl[2,2':5',2''-terthiophen]-3'-yl)ethenyl]-, polymer with 1,1'-[4,8-bis[(2-ethylhexyl)oxy]benzo[1,2-b:4,5-b']dithiophene-2,6-diyl]bis[1,1,1-trimethylstannane]](/data/chemimg/3782800/1695575-72-4.png)
![2-Thiophenecarboxaldehyde, 5-[(1E)-2-(5,5''-dibromo-4,4''-dihexyl[2,2':5',2''-terthiophen]-3'-yl)ethenyl]-, polymer with 1,1'-[4,8-bis[(2-ethylhexyl)oxy]benzo[1,2-b:4,5-b']dithiophene-2,6-diyl]bis[1,1,1-trimethylstannane]](/data/chemimg/3782800/1695575-72-4_b.png)
![2,1,3-Benzothiadiazole, 4-[5-[2-(2,5-dibromothieno[3,2-b]thien-3-yl)ethenyl]-4-hexyl-2-thienyl]-7-(4-hexyl-2-thienyl)-](/data/chemimg/3782800/1714089-73-2.png)
![2,1,3-Benzothiadiazole, 4-[5-[2-(2,5-dibromothieno[3,2-b]thien-3-yl)ethenyl]-4-hexyl-2-thienyl]-7-(4-hexyl-2-thienyl)-](/data/chemimg/3782800/1714089-73-2_b.png)
![2,1,3-Benzothiadiazole, 4-[5-[2-(2,5-dibromothieno[3,2-b]thien-3-yl)ethenyl]-4-hexyl-2-thienyl]-7-(4-hexyl-2-thienyl)-, polymer with 1,1'-[4,8-bis[(2-ethylhexyl)oxy]benzo[1,2-b:4,5-b']dithiophene-2,6-diyl]bis[1,1,1-trimethylstannane]](/data/chemimg/3782800/1714089-74-3.png)
![2,1,3-Benzothiadiazole, 4-[5-[2-(2,5-dibromothieno[3,2-b]thien-3-yl)ethenyl]-4-hexyl-2-thienyl]-7-(4-hexyl-2-thienyl)-, polymer with 1,1'-[4,8-bis[(2-ethylhexyl)oxy]benzo[1,2-b:4,5-b']dithiophene-2,6-diyl]bis[1,1,1-trimethylstannane]](/data/chemimg/3782800/1714089-74-3_b.png)
![2,1,3-Benzothiadiazole, 4-[5-[2-(2,5-dibromo-3-thienyl)ethenyl]-6-heptylthieno[3,2-b]thien-2-yl]-7-(6-heptylthieno[3,2-b]thien-2-yl)-](/data/chemimg/3782800/1714089-75-4.png)
![2,1,3-Benzothiadiazole, 4-[5-[2-(2,5-dibromo-3-thienyl)ethenyl]-6-heptylthieno[3,2-b]thien-2-yl]-7-(6-heptylthieno[3,2-b]thien-2-yl)-](/data/chemimg/3782800/1714089-75-4_b.png)
![2,1,3-Benzothiadiazole, 4-[5-[2-(2,5-dibromo-3-thienyl)ethenyl]-6-heptylthieno[3,2-b]thien-2-yl]-7-(6-heptylthieno[3,2-b]thien-2-yl)-, polymer with 1,1'-[4,8-bis[(2-ethylhexyl)oxy]benzo[1,2-b:4,5-b']dithiophene-2,6-diyl]bis[1,1,1-trimethylstannane]](/data/chemimg/3782800/1714089-76-5.png)
![2,1,3-Benzothiadiazole, 4-[5-[2-(2,5-dibromo-3-thienyl)ethenyl]-6-heptylthieno[3,2-b]thien-2-yl]-7-(6-heptylthieno[3,2-b]thien-2-yl)-, polymer with 1,1'-[4,8-bis[(2-ethylhexyl)oxy]benzo[1,2-b:4,5-b']dithiophene-2,6-diyl]bis[1,1,1-trimethylstannane]](/data/chemimg/3782800/1714089-76-5_b.png)
![Thieno[3,2-b]thiophene, 2,5-dibromo-3-(bromomethyl)-](/data/chemimg/3782800/1714089-77-6.png)
![Thieno[3,2-b]thiophene, 2,5-dibromo-3-(bromomethyl)-](/data/chemimg/3782800/1714089-77-6_b.png)
![Stannane, tributyl(6-heptylthieno[3,2-b]thien-2-yl)-](/data/chemimg/3782800/1714089-80-1.png)
![Stannane, tributyl(6-heptylthieno[3,2-b]thien-2-yl)-](/data/chemimg/3782800/1714089-80-1_b.png)
![2,1,3-Benzothiadiazole, 4,7-bis(6-heptylthieno[3,2-b]thien-2-yl)-](/data/chemimg/3782800/1714089-81-2.png)
![2,1,3-Benzothiadiazole, 4,7-bis(6-heptylthieno[3,2-b]thien-2-yl)-](/data/chemimg/3782800/1714089-81-2_b.png)
![Thieno[3,2-b]thiophene-2-carboxaldehyde, 3-heptyl-5-[7-(6-heptylthieno[3,2-b]thien-2-yl)-2,1,3-benzothiadiazol-4-yl]-](/data/chemimg/3782800/1714089-82-3.png)
![Thieno[3,2-b]thiophene-2-carboxaldehyde, 3-heptyl-5-[7-(6-heptylthieno[3,2-b]thien-2-yl)-2,1,3-benzothiadiazol-4-yl]-](/data/chemimg/3782800/1714089-82-3_b.png)
![[2,2'-Bithiophene]-5-carboxaldehyde, 4-hexyl-](/data/chemimg/3782800/1799505-54-6.png)
![[2,2'-Bithiophene]-5-carboxaldehyde, 4-hexyl-](/data/chemimg/3782800/1799505-54-6_b.png)
![[2,2'-Bithiophene]-5-carboxaldehyde, 5'-bromo-4-hexyl-](/data/chemimg/3782800/1799505-55-7.png)
![[2,2'-Bithiophene]-5-carboxaldehyde, 5'-bromo-4-hexyl-](/data/chemimg/3782800/1799505-55-7_b.png)
![[2,2'-Bithiophene]-5-carboxaldehyde, 5'-[10-(2-ethylhexyl)-10H-phenothiazin-3-yl]-4-hexyl-](/data/chemimg/3782800/1799505-56-8.png)
![[2,2'-Bithiophene]-5-carboxaldehyde, 5'-[10-(2-ethylhexyl)-10H-phenothiazin-3-yl]-4-hexyl-](/data/chemimg/3782800/1799505-56-8_b.png)
![2-Thiophenecarboxaldehyde, 5-[7-[10-(2-ethylhexyl)-10H-phenothiazin-3-yl]-2,1,3-benzothiadiazol-4-yl]-3-hexyl-](/data/chemimg/3782800/1799505-57-9.png)
![2-Thiophenecarboxaldehyde, 5-[7-[10-(2-ethylhexyl)-10H-phenothiazin-3-yl]-2,1,3-benzothiadiazol-4-yl]-3-hexyl-](/data/chemimg/3782800/1799505-57-9_b.png)
![Benzenamine, N,N-bis(4-methylphenyl)-4-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10H-phenothiazin-10-yl]-](/data/chemimg/3782800/1799505-59-1.png)
![Benzenamine, N,N-bis(4-methylphenyl)-4-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10H-phenothiazin-10-yl]-](/data/chemimg/3782800/1799505-59-1_b.png)
![2-Thiophenecarboxaldehyde, 5-[7-[10-[4-[bis(4-methylphenyl)amino]phenyl]-10H-phenothiazin-3-yl]-2,1,3-benzothiadiazol-4-yl]-3-hexyl-](/data/chemimg/3782800/1799505-60-4.png)
![2-Thiophenecarboxaldehyde, 5-[7-[10-[4-[bis(4-methylphenyl)amino]phenyl]-10H-phenothiazin-3-yl]-2,1,3-benzothiadiazol-4-yl]-3-hexyl-](/data/chemimg/3782800/1799505-60-4_b.png)
![2-Propenoic acid, 2-cyano-3-[5'-[10-(2-ethylhexyl)-10H-phenothiazin-3-yl]-4-hexyl[2,2'-bithiophen]-5-yl]-](/data/chemimg/3782800/1799505-61-5.png)
![2-Propenoic acid, 2-cyano-3-[5'-[10-(2-ethylhexyl)-10H-phenothiazin-3-yl]-4-hexyl[2,2'-bithiophen]-5-yl]-](/data/chemimg/3782800/1799505-61-5_b.png)
![2-Propenoic acid, 2-cyano-3-[5-[7-[10-(2-ethylhexyl)-10H-phenothiazin-3-yl]-2,1,3-benzothiadiazol-4-yl]-3-hexyl-2-thienyl]-](/data/chemimg/3782800/1799505-62-6.png)
![2-Propenoic acid, 2-cyano-3-[5-[7-[10-(2-ethylhexyl)-10H-phenothiazin-3-yl]-2,1,3-benzothiadiazol-4-yl]-3-hexyl-2-thienyl]-](/data/chemimg/3782800/1799505-62-6_b.png)
![2-Propenoic acid, 3-[5-[7-[10-[4-[bis(4-methylphenyl)amino]phenyl]-10H-phenothiazin-3-yl]-2,1,3-benzothiadiazol-4-yl]-3-hexyl-2-thienyl]-2-cyano-](/data/chemimg/3782800/1799505-63-7.png)
![2-Propenoic acid, 3-[5-[7-[10-[4-[bis(4-methylphenyl)amino]phenyl]-10H-phenothiazin-3-yl]-2,1,3-benzothiadiazol-4-yl]-3-hexyl-2-thienyl]-2-cyano-](/data/chemimg/3782800/1799505-63-7_b.png)
![Thieno[3,2-b]thiophene-2-carboxylic acid, 5-bromo-3-methyl-, methyl ester](/data/chemimg/3782800/1800009-31-7.png)
![Thieno[3,2-b]thiophene-2-carboxylic acid, 5-bromo-3-methyl-, methyl ester](/data/chemimg/3782800/1800009-31-7_b.png)
![Thieno[3,2-b]thiophene-2-carboxylic acid, 3-methyl-5-[2-(trimethylsilyl)ethynyl]-, methyl ester](/data/chemimg/3782800/1800009-32-8.png)
![Thieno[3,2-b]thiophene-2-carboxylic acid, 3-methyl-5-[2-(trimethylsilyl)ethynyl]-, methyl ester](/data/chemimg/3782800/1800009-32-8_b.png)
![Thieno[3,2-b]thiophene-2-carboxylic acid, 5-ethynyl-3-methyl-](/data/chemimg/3782800/1800009-33-9.png)
![Thieno[3,2-b]thiophene-2-carboxylic acid, 5-ethynyl-3-methyl-](/data/chemimg/3782800/1800009-33-9_b.png)
![2,1,3-Benzothiadiazole, 4,7-dibromo-5-[2-[3-hexyl-5-[7-(4-hexyl-2-thienyl)-2,1,3-benzothiadiazol-4-yl]-2-thienyl]ethenyl]-](/data/chemimg/3782800/1812882-66-8.png)
![2,1,3-Benzothiadiazole, 4,7-dibromo-5-[2-[3-hexyl-5-[7-(4-hexyl-2-thienyl)-2,1,3-benzothiadiazol-4-yl]-2-thienyl]ethenyl]-](/data/chemimg/3782800/1812882-66-8_b.png)
![Quinoxaline, 5,8-dibromo-2-[2-[3-hexyl-5-[7-(4-hexyl-2-thienyl)-2,1,3-benzothiadiazol-4-yl]-2-thienyl]ethenyl]-3-methyl-](/data/chemimg/3782800/1812882-69-1.png)
![Quinoxaline, 5,8-dibromo-2-[2-[3-hexyl-5-[7-(4-hexyl-2-thienyl)-2,1,3-benzothiadiazol-4-yl]-2-thienyl]ethenyl]-3-methyl-](/data/chemimg/3782800/1812882-69-1_b.png)
![2-Propenoic acid, 3-[5-[4-[bis(4-methylphenyl)amino]phenyl]-4-(1E,3E)-1,3-heptadien-1-yl-2-thienyl]-2-cyano-, (2E)-](/data/chemimg/3782800/1818207-53-2.png)
![2-Propenoic acid, 3-[5-[4-[bis(4-methylphenyl)amino]phenyl]-4-(1E,3E)-1,3-heptadien-1-yl-2-thienyl]-2-cyano-, (2E)-](/data/chemimg/3782800/1818207-53-2_b.png)
![2-Propenoic acid, 3-[5-[4-[bis(4-methylphenyl)amino]phenyl]-4-[(1E)-2-(5-hexyl-2-thienyl)ethenyl]-2-thienyl]-2-cyano-, (2E)-](/data/chemimg/3782800/1818207-54-3.png)
![2-Propenoic acid, 3-[5-[4-[bis(4-methylphenyl)amino]phenyl]-4-[(1E)-2-(5-hexyl-2-thienyl)ethenyl]-2-thienyl]-2-cyano-, (2E)-](/data/chemimg/3782800/1818207-54-3_b.png)
![2-Propenoic acid, 3-[5-[4-[bis(4-methylphenyl)amino]phenyl]-4-[(1E)-2-[5-[10-(2-ethylhexyl)-10H-phenoxazin-3-yl]-2-thienyl]ethenyl]-2-thienyl]-2-cyano-, (2E)-](/data/chemimg/3782800/1818207-55-4.png)
![2-Propenoic acid, 3-[5-[4-[bis(4-methylphenyl)amino]phenyl]-4-[(1E)-2-[5-[10-(2-ethylhexyl)-10H-phenoxazin-3-yl]-2-thienyl]ethenyl]-2-thienyl]-2-cyano-, (2E)-](/data/chemimg/3782800/1818207-55-4_b.png)
![Thiophene, 2-bromo-3-[(1E)-2-(5-hexyl-2-thienyl)ethenyl]-](/data/chemimg/3782800/1818207-60-1.png)
![Thiophene, 2-bromo-3-[(1E)-2-(5-hexyl-2-thienyl)ethenyl]-](/data/chemimg/3782800/1818207-60-1_b.png)
![10H-Phenoxazine, 3-[5-[(1E)-2-(2-bromo-3-thienyl)ethenyl]-2-thienyl]-10-(2-ethylhexyl)-](/data/chemimg/3782800/1818207-61-2.png)
![10H-Phenoxazine, 3-[5-[(1E)-2-(2-bromo-3-thienyl)ethenyl]-2-thienyl]-10-(2-ethylhexyl)-](/data/chemimg/3782800/1818207-61-2_b.png)
![Benzenamine, 4-[3-(1E,3E)-1,3-heptadien-1-yl-2-thienyl]-N,N-bis(4-methylphenyl)-](/data/chemimg/3782800/1818207-62-3.png)
![Benzenamine, 4-[3-(1E,3E)-1,3-heptadien-1-yl-2-thienyl]-N,N-bis(4-methylphenyl)-](/data/chemimg/3782800/1818207-62-3_b.png)
![Benzenamine, 4-[3-[(1E)-2-(5-hexyl-2-thienyl)ethenyl]-2-thienyl]-N,N-bis(4-methylphenyl)-](/data/chemimg/3782800/1818207-63-4.png)
![Benzenamine, 4-[3-[(1E)-2-(5-hexyl-2-thienyl)ethenyl]-2-thienyl]-N,N-bis(4-methylphenyl)-](/data/chemimg/3782800/1818207-63-4_b.png)
![Benzenamine, 4-[3-[(1E)-2-[5-[10-(2-ethylhexyl)-10H-phenoxazin-3-yl]-2-thienyl]ethenyl]-2-thienyl]-N,N-bis(4-methylphenyl)-](/data/chemimg/3782800/1818207-64-5.png)
![Benzenamine, 4-[3-[(1E)-2-[5-[10-(2-ethylhexyl)-10H-phenoxazin-3-yl]-2-thienyl]ethenyl]-2-thienyl]-N,N-bis(4-methylphenyl)-](/data/chemimg/3782800/1818207-64-5_b.png)
![2-Thiophenecarboxaldehyde, 5-[4-[bis(4-methylphenyl)amino]phenyl]-4-(1E,3E)-1,3-heptadien-1-yl-](/data/chemimg/3782800/1818207-65-6.png)
![2-Thiophenecarboxaldehyde, 5-[4-[bis(4-methylphenyl)amino]phenyl]-4-(1E,3E)-1,3-heptadien-1-yl-](/data/chemimg/3782800/1818207-65-6_b.png)
![2-Thiophenecarboxaldehyde, 5-[4-[bis(4-methylphenyl)amino]phenyl]-4-[(1E)-2-(5-hexyl-2-thienyl)ethenyl]-](/data/chemimg/3782800/1818207-66-7.png)
![2-Thiophenecarboxaldehyde, 5-[4-[bis(4-methylphenyl)amino]phenyl]-4-[(1E)-2-(5-hexyl-2-thienyl)ethenyl]-](/data/chemimg/3782800/1818207-66-7_b.png)
![2-Thiophenecarboxaldehyde, 5-[4-[bis(4-methylphenyl)amino]phenyl]-4-[(1E)-2-[5-[10-(2-ethylhexyl)-10H-phenoxazin-3-yl]-2-thienyl]ethenyl]-](/data/chemimg/3782800/1818207-67-8.png)
![2-Thiophenecarboxaldehyde, 5-[4-[bis(4-methylphenyl)amino]phenyl]-4-[(1E)-2-[5-[10-(2-ethylhexyl)-10H-phenoxazin-3-yl]-2-thienyl]ethenyl]-](/data/chemimg/3782800/1818207-67-8_b.png)
![2,1,3-Benzothiadiazole, 4-[5-[2-(2,5-dibromo-3-thienyl)ethenyl]-4-octyl-2-thienyl]-7-(4-octyl-2-thienyl)-](/data/chemimg/3782800/1820757-63-8.png)
![2,1,3-Benzothiadiazole, 4-[5-[2-(2,5-dibromo-3-thienyl)ethenyl]-4-octyl-2-thienyl]-7-(4-octyl-2-thienyl)-](/data/chemimg/3782800/1820757-63-8_b.png)
![4H-Indeno[1,2-b]thiophen-6-amine, N,N,4,4-tetrakis(4-methylphenyl)-2-(tributylstannyl)-](/data/chemimg/3782800/1859128-16-7.png)
![4H-Indeno[1,2-b]thiophen-6-amine, N,N,4,4-tetrakis(4-methylphenyl)-2-(tributylstannyl)-](/data/chemimg/3782800/1859128-16-7_b.png)
![[2,2'-Bithiophene]-5-carboxaldehyde, 3-hexyl-](/data/chemimg/3782800/1883669-93-9.png)
![[2,2'-Bithiophene]-5-carboxaldehyde, 3-hexyl-](/data/chemimg/3782800/1883669-93-9_b.png)
![Pyrrolo[3,4-c]pyrrole-1,4-dione, 3-[5'-[(1E)-2-(2,5-dibromo-3-thienyl)ethenyl][2,2'-bithiophen]-5-yl]-2,5-bis(2-ethylhexyl)-2,5-dihydro-6-(2-thienyl)-](/data/chemimg/3730300/2050338-51-5.png)
![Pyrrolo[3,4-c]pyrrole-1,4-dione, 3-[5'-[(1E)-2-(2,5-dibromo-3-thienyl)ethenyl][2,2'-bithiophen]-5-yl]-2,5-bis(2-ethylhexyl)-2,5-dihydro-6-(2-thienyl)-](/data/chemimg/3730300/2050338-51-5_b.png)
![Benzoic acid, 4-[5-[6-[bis(4-methylphenyl)amino]-4,4-bis(4-methylphenyl)-4H-indeno[1,2-b]thien-2-yl]-2-thienyl]-](/data/chemimg/3782800/2080446-88-2.png)
![Benzoic acid, 4-[5-[6-[bis(4-methylphenyl)amino]-4,4-bis(4-methylphenyl)-4H-indeno[1,2-b]thien-2-yl]-2-thienyl]-](/data/chemimg/3782800/2080446-88-2_b.png)
![Benzoic acid, 4-[7-[5-[6-[bis(4-methylphenyl)amino]-4,4-bis(4-methylphenyl)-4H-indeno[1,2-b]thien-2-yl]-2-thienyl]-2,1,3-benzothiadiazol-4-yl]-](/data/chemimg/3782800/2080446-89-3.png)
![Benzoic acid, 4-[7-[5-[6-[bis(4-methylphenyl)amino]-4,4-bis(4-methylphenyl)-4H-indeno[1,2-b]thien-2-yl]-2-thienyl]-2,1,3-benzothiadiazol-4-yl]-](/data/chemimg/3782800/2080446-89-3_b.png)
![Benzoic acid, 4-[5-[4-[5-[6-[bis(4-methylphenyl)amino]-4,4-bis(4-methylphenyl)-4H-indeno[1,2-b]thien-2-yl]-2-thienyl]-2,5-bis(2-ethylhexyl)-2,3,5,6-tetrahydro-3,6-dioxopyrrolo[3,4-c]pyrrol-1-yl]-2-thienyl]-](/data/chemimg/3777600/2080446-90-6.png)
![Benzoic acid, 4-[5-[4-[5-[6-[bis(4-methylphenyl)amino]-4,4-bis(4-methylphenyl)-4H-indeno[1,2-b]thien-2-yl]-2-thienyl]-2,5-bis(2-ethylhexyl)-2,3,5,6-tetrahydro-3,6-dioxopyrrolo[3,4-c]pyrrol-1-yl]-2-thienyl]-](/data/chemimg/3777600/2080446-90-6_b.png)
![Benzoic acid, 4-[7-(2-thienyl)-2,1,3-benzothiadiazol-4-yl]-, methyl ester](/data/chemimg/3782800/2080446-91-7.png)
![Benzoic acid, 4-[7-(2-thienyl)-2,1,3-benzothiadiazol-4-yl]-, methyl ester](/data/chemimg/3782800/2080446-91-7_b.png)
![Benzoic acid, 4-[7-(5-bromo-2-thienyl)-2,1,3-benzothiadiazol-4-yl]-, methyl ester](/data/chemimg/3782800/2080446-92-8.png)
![Benzoic acid, 4-[7-(5-bromo-2-thienyl)-2,1,3-benzothiadiazol-4-yl]-, methyl ester](/data/chemimg/3782800/2080446-92-8_b.png)
![Benzoic acid, 4-[5-[6-[bis(4-methylphenyl)amino]-4,4-bis(4-methylphenyl)-4H-indeno[1,2-b]thien-2-yl]-2-thienyl]-, methyl ester](/data/chemimg/3782800/2080446-94-0.png)
![Benzoic acid, 4-[5-[6-[bis(4-methylphenyl)amino]-4,4-bis(4-methylphenyl)-4H-indeno[1,2-b]thien-2-yl]-2-thienyl]-, methyl ester](/data/chemimg/3782800/2080446-94-0_b.png)
![Benzoic acid, 4-[7-[5-[6-[bis(4-methylphenyl)amino]-4,4-bis(4-methylphenyl)-4H-indeno[1,2-b]thien-2-yl]-2-thienyl]-2,1,3-benzothiadiazol-4-yl]-, methyl ester](/data/chemimg/3782800/2080446-95-1.png)
![Benzoic acid, 4-[7-[5-[6-[bis(4-methylphenyl)amino]-4,4-bis(4-methylphenyl)-4H-indeno[1,2-b]thien-2-yl]-2-thienyl]-2,1,3-benzothiadiazol-4-yl]-, methyl ester](/data/chemimg/3782800/2080446-95-1_b.png)
![Benzoic acid, 4-[5-[4-[5-[6-[bis(4-methylphenyl)amino]-4,4-bis(4-methylphenyl)-4H-indeno[1,2-b]thien-2-yl]-2-thienyl]-2,5-bis(2-ethylhexyl)-2,3,5,6-tetrahydro-3,6-dioxopyrrolo[3,4-c]pyrrol-1-yl]-2-thienyl]-, methyl ester](/data/chemimg/3782800/2080446-96-2.png)
![Benzoic acid, 4-[5-[4-[5-[6-[bis(4-methylphenyl)amino]-4,4-bis(4-methylphenyl)-4H-indeno[1,2-b]thien-2-yl]-2-thienyl]-2,5-bis(2-ethylhexyl)-2,3,5,6-tetrahydro-3,6-dioxopyrrolo[3,4-c]pyrrol-1-yl]-2-thienyl]-, methyl ester](/data/chemimg/3782800/2080446-96-2_b.png)
![2,1,3-Benzothiadiazole, 4-[5-[(1E)-2-(2,5-dibromo-3-thienyl)ethenyl]-4-hexyl-2-thienyl]-5,6-difluoro-7-(4-hexyl-2-thienyl)-](/data/chemimg/3782800/2102523-15-7.png)
![2,1,3-Benzothiadiazole, 4-[5-[(1E)-2-(2,5-dibromo-3-thienyl)ethenyl]-4-hexyl-2-thienyl]-5,6-difluoro-7-(4-hexyl-2-thienyl)-](/data/chemimg/3782800/2102523-15-7_b.png)
![2,1,3-Benzothiadiazole, 4-[5-[(1E)-2-(2-bromo-3-thienyl)ethenyl]-4-hexyl-2-thienyl]-5,6-difluoro-7-(3-hexyl-5'-methyl[2,2'-bithiophen]-5-yl)-](/data/chemimg/3782700/2103287-67-6.png)
![2,1,3-Benzothiadiazole, 4-[5-[(1E)-2-(2-bromo-3-thienyl)ethenyl]-4-hexyl-2-thienyl]-5,6-difluoro-7-(3-hexyl-5'-methyl[2,2'-bithiophen]-5-yl)-](/data/chemimg/3782700/2103287-67-6_b.png)
![Benzoic acid, 4-[5,6-difluoro-7-(2-thienyl)-2,1,3-benzothiadiazol-4-yl]-, methyl ester](/data/chemimg/3782700/2115699-07-3.png)
![Benzoic acid, 4-[5,6-difluoro-7-(2-thienyl)-2,1,3-benzothiadiazol-4-yl]-, methyl ester](/data/chemimg/3782700/2115699-07-3_b.png)
![Benzoic acid, 4-[7-[5-[3,5-bis[(1E)-2-[4-[bis(4-methylphenyl)amino]phenyl]ethenyl]-4-(octyloxy)phenyl]-2-thienyl]-5,6-difluoro-2,1,3-benzothiadiazol-4-yl]-](/data/chemimg/3782700/2115699-24-4.png)
![Benzoic acid, 4-[7-[5-[3,5-bis[(1E)-2-[4-[bis(4-methylphenyl)amino]phenyl]ethenyl]-4-(octyloxy)phenyl]-2-thienyl]-5,6-difluoro-2,1,3-benzothiadiazol-4-yl]-](/data/chemimg/3782700/2115699-24-4_b.png)
![Benzoic acid, 4-[5-[4-[5-[3,5-bis[(1E)-2-[4-[bis(4-methylphenyl)amino]phenyl]ethenyl]-4-(octyloxy)phenyl]-2-thienyl]-2,5-bis(2-ethylhexyl)-2,3,5,6-tetrahydro-3,6-dioxopyrrolo[3,4-c]pyrrol-1-yl]-2-thienyl]-](/data/chemimg/3782700/2115707-31-6.png)
![Benzoic acid, 4-[5-[4-[5-[3,5-bis[(1E)-2-[4-[bis(4-methylphenyl)amino]phenyl]ethenyl]-4-(octyloxy)phenyl]-2-thienyl]-2,5-bis(2-ethylhexyl)-2,3,5,6-tetrahydro-3,6-dioxopyrrolo[3,4-c]pyrrol-1-yl]-2-thienyl]-](/data/chemimg/3782700/2115707-31-6_b.png)
![Benzoic acid, 4-[7-(5-bromo-2-thienyl)-5,6-difluoro-2,1,3-benzothiadiazol-4-yl]-, methyl ester](/data/chemimg/3782700/2118231-53-9.png)
![Benzoic acid, 4-[7-(5-bromo-2-thienyl)-5,6-difluoro-2,1,3-benzothiadiazol-4-yl]-, methyl ester](/data/chemimg/3782700/2118231-53-9_b.png)
![Benzoic acid, 4-[7-[5-[3,5-bis[(1E)-2-[4-[bis(4-methylphenyl)amino]phenyl]ethenyl]-4-(octyloxy)phenyl]-2-thienyl]-5,6-difluoro-2,1,3-benzothiadiazol-4-yl]-, methyl ester](/data/chemimg/3782700/2118231-55-1.png)
![Benzoic acid, 4-[7-[5-[3,5-bis[(1E)-2-[4-[bis(4-methylphenyl)amino]phenyl]ethenyl]-4-(octyloxy)phenyl]-2-thienyl]-5,6-difluoro-2,1,3-benzothiadiazol-4-yl]-, methyl ester](/data/chemimg/3782700/2118231-55-1_b.png)
![Benzoic acid, 4-[5-[4-[5-[3,5-bis[(1E)-2-[4-[bis(4-methylphenyl)amino]phenyl]ethenyl]-4-(octyloxy)phenyl]-2-thienyl]-2,5-bis(2-ethylhexyl)-2,3,5,6-tetrahydro-3,6-dioxopyrrolo[3,4-c]pyrrol-1-yl]-2-thienyl]-, methyl ester](/data/chemimg/3782700/2118231-56-2.png)
![Benzoic acid, 4-[5-[4-[5-[3,5-bis[(1E)-2-[4-[bis(4-methylphenyl)amino]phenyl]ethenyl]-4-(octyloxy)phenyl]-2-thienyl]-2,5-bis(2-ethylhexyl)-2,3,5,6-tetrahydro-3,6-dioxopyrrolo[3,4-c]pyrrol-1-yl]-2-thienyl]-, methyl ester](/data/chemimg/3782700/2118231-56-2_b.png)