Co-reporter:Helin Wang, Lingcheng Chen, Zhenbo Zhao, Yi Xiao
Dyes and Pigments 2017 Volume 144(Volume 144) pp:
Publication Date(Web):1 September 2017
DOI:10.1016/j.dyepig.2017.05.030
A series of aryl-bisalkynyl bridged perylene diimides derivatives were efficiently synthesized through the Sonogashira-type coupling reaction, and their photophysical, electrochemical and electron-transporting properties were investigated in detail. With the introduction of aryl-bisalkynyl groups, their absorption spectra exhibit extra strong absorption in the short wavelength region and therefore realizing broad wavelength range from 300 to 700 nm, which can overcome the weakness of narrow half-peak width of N,N'-bis(1-ethylpropyl)perylene-3,4,9,10-tetracarboxylic acid bisimides (PDI). The lowest unoccupied molecular orbital (LUMO) levels (about −4.00 eV) are lower than that of the prototype PDI, which make them potential for excellent electron-transporting materials. As a result, the improved electron mobilities of 10−4 cm2 V−1 s−1, which is three orders of magnitude higher than that of PDI, were obtained in space charge limited current (SCLC) devices.
Co-reporter:Helin Wang;Yi Xiao
Journal of Materials Chemistry C 2017 vol. 5(Issue 34) pp:8875-8882
Publication Date(Web):2017/08/31
DOI:10.1039/C7TC03171H
A new family of perylene diimide (PDI) arrays, heterologous ones (di-PDI and tri-PDI), were designed and efficiently synthesized by Suzuki cross-coupling reactions using two heterologous PDI monomers with different positions of bay- and ortho-substitution, respectively. The compounds exhibit unique photophysical and electrochemical properties and were successfully applied in non-fullerene organic solar cells with a superior power conversion efficiency of 4.55% for tri-PDI.
Co-reporter:Helin Wang;Yi Xiao
Journal of Materials Chemistry A 2017 vol. 5(Issue 42) pp:22288-22296
Publication Date(Web):2017/10/31
DOI:10.1039/C7TA06804B
A simple molecular structure of ortho-derived perylene diimide (PDI) diploid (oo-2PDI), a PDI derivative, as well as two bay-derived PDI diploids (bb-2PDI and bo-2PDI), was designed and efficiently synthesized by efficient Ullmann coupling reactions. The photophysical and electrochemical properties indicate that oo-2PDI exhibits much stronger absorption than bb-2PDI in the visible region and a slightly higher lowest unoccupied molecular orbital (LUMO) level, which are beneficial for harvesting much sunlight and improving open circuit voltage in the organic solar cell (OSC) devices. On using PTB7-Th with appropriate energy level alignment and well matched absorption as the electron donor, the active layer of PTB7-Th:oo-2PDI exhibits a favorable morphology, higher carrier mobilities and more balanced carrier transport. As a result, the device based on PTB7-Th:oo-2PDI shows a power conversion efficiency (PCE) as high as 8.30% and a high short circuit current (JSC) of 18.79 mA cm−2, which are much higher than those of the other two PDI diploids (bb-2PDI and bo-2PDI), highlighting the potential of ortho-derived PDI diploid to realize high efficiency non-fullerene OSCs. Such a concise molecular structure and the high efficiency make this compound promising for practical applications in OSCs.
Co-reporter:Helin Wang;Yi Xiao
Journal of Materials Chemistry C 2017 vol. 5(Issue 48) pp:12816-12824
Publication Date(Web):2017/12/14
DOI:10.1039/C7TC04726F
Herein, two perylene diimide (PDI) trimer arrays (bbb-3PDI and obo-3PDI), which are coupled at different reactive positions of the PDI monomer, have been efficiently synthesized and comprehensively investigated. The photophysical and electrochemical properties indicate that these two compounds exhibit much strong absorption in the visible region and suitable lowest unoccupied molecular orbital (LUMO) levels. In addition, the density functional theory (DFT) calculations indicate that the compound bbb-3PDI possesses stronger abilities of accepting electrons from donors and donating holes to the donor materials; thus, this compound is beneficial for exciton dissociation in OSCs. Upon choosing an appropriate energy level alignment and PTB7-Th with well-matched absorption as electron donors, the active layer of PTB7-Th:bbb-3PDI exhibits favorable morphology, higher carrier mobilities, and more balanced carrier transport. As a result, the device based on PTB7-Th:bbb-3PDI shows a high power conversion efficiency (PCE) of 7.12% and a high short circuit current (JSC) of 18.13 mA cm−2, which are the highest values obtained for the PDI-array-based non-fullerene OSCs. The obtained performance based on bbb-3PDI is significantly higher than those of obo-3PDI (4.55%) and the PDI dimer arrays; this highlights the potential of the PDI trimer arrays to realize high-efficiency non-fullerene OSCs.
Co-reporter:Xinfu Zhang, Youdi Zhang, Lingcheng Chen and Yi Xiao
RSC Advances 2015 vol. 5(Issue 41) pp:32283-32289
Publication Date(Web):31 Mar 2015
DOI:10.1039/C5RA02414E
A series of tunable absorbing star-shaped BODIPY derivatives containing a different number of carbazole units were designed and synthesized. With the extended conjugated skeleton, their absorption spectra become progressively bathochromic shifted from the red region to the near-infrared region. The compound TAC with four carbazole units exhibits a strong near-infrared absorption up to 850 nm with a high extinction coefficient over 135000 M−1 cm−1 and considerable intrinsic hole mobility of 4.82 × 10−5 cm2 V−1 s−1 in SCLC devices. The near-infrared organic solar cells (OSCs) based on TAC exhibit a potential power conversion efficiency of 2.70% and a high open-circuit voltage of 0.85 V.
Co-reporter:Youdi Zhang;Dr. Lingcheng Chen;Kaichen Zhang;Helin Wang ; Yi Xiao
Chemistry - A European Journal 2014 Volume 20( Issue 32) pp:10170-10178
Publication Date(Web):
DOI:10.1002/chem.201402100
Abstract
A new ladder-conjugated star-shaped oligomer electron-transporting material TetraPDI-PF, with four perylene diimide (PDI) branches and a fluorene core, was efficiently synthesized. The oligomer is highly soluble in dichlorobenzene with a solubility of 155 mg mL−1, which is higher than those of PDI (35 mg mL−1) and PDI-Phen (70 mg mL−1). Demonstrated by thermogravimetric analysis (TGA), the oligomer exhibits excellent thermal stability with the decomposition temperature (Td) of 291.2 °C, which is 65 °C higher than that of PDI. Cyclic voltammetry (CV) and differential pulse voltammetry (DPV) were employed to investigate the electrochemical properties. Although the CV curves of TetraPDI-PF are successively scanned for 15 cycles, they still remain invariable reduction potentials. The oligomer also shows outstanding photostability, even better than PDI, which maintains 99 % fluorescence intensity after irradiation for 10 min using maximum laser intensity. In the steady-state space-charge-limited current (SCLC) devices, TetraPDI-PF exhibits higher intrinsic electron mobility of 2.22×10−5 cm2 V−1 s−1, three orders of magnitude over that of PDI (3.52×10−8 cm2 V−1 s−1). The bulk heterojunction (BHJ) organic solar cells (OSCs) using TetraPDI-PF as non-fullerene acceptors and P3HT as donors give optimum power conversion efficiency (PCE) of 0.64 %, which is 64 times that of the PDI:P3HT BHJ cells.
![1H,3H-Perylo[3,4-cd]pyran-1,3-dione, 8-bromo-](http://img.cochemist.com/ccimg/676400/676363-06-7.png)
![1H,3H-Perylo[3,4-cd]pyran-1,3-dione, 8-bromo-](http://img.cochemist.com/ccimg/676400/676363-06-7_b.png)
