Co-reporter:Zhikai Li, Jiali Gu, Shengli Qi, Dezhen Wu, Lingfeng Gao, Ze Chen, Jun Guo, Xiaohong Li, Yong Wang, Xiaoming Yang, and Yingfeng Tu
Journal of the American Chemical Society October 18, 2017 Volume 139(Issue 41) pp:14364-14364
Publication Date(Web):October 6, 2017
DOI:10.1021/jacs.7b07965
We demonstrate here the synthesis of a novel class of metallo-supramolecular polymers with shackled structure, via the coordination of cyclic di(bis-terpyridine-triphenyl ether ester) ligands with ruthenium(II) ions. The constraint from the ring topology via the shackling of ligands provides novel properties to these metallo-supramolecular polymers, including the formation of dendritic crystals, red-shift of absorption bands in the UV–vis spectra from interchain charge-transfer transitions, and a typical flash-type memory behavior.
Co-reporter:Min Lu;Xiang Zhu;Xiao-hong Li;Xiao-ming Yang
Chinese Journal of Polymer Science 2017 Volume 35( Issue 9) pp:1051-1060
Publication Date(Web):05 July 2017
DOI:10.1007/s10118-017-1951-4
We present here the first synthesis of cyclic oligo(ethylene adipate)s (COEAs) via pseudo-high dilution condensation reaction of adipoyl chloride with ethylene glycol, and the synthesis of corresponding poly(ethylene adipate) (PEA) via the melt polymerization of COEAs. The structure of COEAs was characterized and proved by 1H-NMR and MALDI-TOF mass measurements. The effects of organic base, reaction temperature and the ratio of adipoyl chloride to ethylene glycol on the yield of COEAs were studied, and the optimum reaction condition was revealed. PEA, a diacid and diol based semi-crystalline green aliphatic polyester, was synthesized by the melt polymerization of COEAs using Ti(n-C4H9O)4 as catalyst and 1,10-decanediol as initiator at 200 °C, which follows the polycondensation-coupling ring-opening polymerization method. Our strategy should be applicable to the synthesis of versatile aliphatic polyesters based on diacid and diol monomers, which have potential applications as biocompatible and biodegradable materials.
Co-reporter:Tiantian Zhu;Xiaoyan Zhang;Zhikai Li;Chih-Hao Hsu;Wei Chen;Toshikazu Miyoshi;Xiaohong Li;Xiaoming Yang;Christopher Y. Li
Chemical Communications 2017 vol. 53(Issue 59) pp:8336-8339
Publication Date(Web):2017/07/20
DOI:10.1039/C7CC03195E
We present here that in two-dimensional (2D) fullerene supramolecular liquid crystals (SLCs), the phase diagram and lamella thickness of SLCs and 2D crystals can be tuned by the flexible alkyl tail and spacer length, due to their different effects on enthalpy and entropy changes during SLC formation.
Co-reporter:Xiang Zhu;Jiali Gu;Xiaohong Li;Xiaoming Yang;Lian Wang;Yongjin Li;He Li
Polymer Chemistry (2010-Present) 2017 vol. 8(Issue 12) pp:1953-1962
Publication Date(Web):2017/03/21
DOI:10.1039/C7PY00068E
We present here an in situ cascade polycondensation-coupling ring-opening polymerization (PROP) method for the facile synthesis of polyesters with relatively high molecular weights that are hard to synthesize by traditional condensation polymerization methods. The method was developed during our studies on the melt polymerization of three poly(trimethylene terephthalate) (PTT) analogues with different lateral alkyl chains at the β-position of 1,3-propanediol, i.e., poly(2-methyl-1,3-propylene terephthalate) (PMPT), poly(neopentylene terephthalate) (PNT) and poly(2-methyl-2-propyl-1,3-propylene terephthalate) (PMPPT), from their corresponding cyclic oligoesters using diol initiators. Kinetic studies suggest that the systems follow the ring-opening polymerization mechanism at the early stages to form diol end-functionalized polyesters, while, subsequently, condensation polymerization starts between the polyesters at high monomer conversion regions. Inspired by the “domino reaction” concept in organic chemistry, the above in situ cascade polymerization process is attributed to a “domino polymerization” method. The structure–property relationship of these polyesters was investigated. It shows that the introduction of alkyl chains on the lateral side of propanediol segments increases the polyesters’ Tg by improving the chain stiffness, as those with higher modulus exhibit higher Tg, yet the gas barrier properties decrease with more or longer alkyl chains introduced. Our PROP method affords a facile way to synthesize polyesters and copolyesters with functional groups for potential application in materials science.
Co-reporter:Weichun Huang, Qiwei Pan, Hao Qi, Xiaohong Li, Yingfeng Tu, Christopher Y. Li
Polymer 2017 Volume 128(Volume 128) pp:
Publication Date(Web):16 October 2017
DOI:10.1016/j.polymer.2017.09.027
•(PBT-b-PEO-b-PBT)n multiblock copolymers (mBCPs) were synthesized using PROP method.•mBCP-based solid polymer electrolytes (SPEs) were fabricated with tunable properties.•The mBPC-based SPEs are promising for all-solid-state lithium battery applications.We presented here the synthesis of poly(butylene terephthalate) (PBT) and poly(ethylene oxide) (PEO) alternating multiblock copolymers (mBCPs), (PBT-b-PEO-b-PBT)n, via a novel cascade polycondensation-coupling ring-opening polymerization (PROP) method. The chemical structure of (PBT-b-PEO-b-PBT)n mBCPs was revealed by 1D and 2D NMR techniques. By blending with lithium bis(trifluoromethane)sulfonamide (up to r ≡ [Li+]/[EO] of 0.20), the mBCP-based solid polymer electrolytes (SPEs) show excellent performance in all-solid-state lithium batteries. Impedance spectroscopy showed that a maximum ionic conductivity, ∼8.2 × 10−4 S/cm at 90 °C, was achieved at r = 0.10 for the mBCP (76 wt.% PEO) SPEs. A high Cd (charge passed through the symmetric cell before short-circuit) of 441 C/cm2 was achieved at the current density of 0.3 mA/cm2 at 90 °C. Because of the facile synthesis, the rich molecular architecture of mBCP, and the high melting point of PBT, these new mBCP SPEs provide a new platform for SPE design.Download high-res image (171KB)Download full-size image
Co-reporter:Dong-xue Chen;Ling-feng Gao;Xiao-hong Li 李晓虹
Chinese Journal of Polymer Science 2017 Volume 35( Issue 5) pp:681-692
Publication Date(Web):2017 May
DOI:10.1007/s10118-017-1919-4
We present here the application of one-dimensional and two-dimensional NMR techniques to characterize the structure of methoxyl end-functionalized polystyrenes (PS). The peaks in 1H-NMR spectra corresponding to main-chain, side-chain and chain-end groups are assigned by 1H-1H gCOSY, 1H-13C gHSQC and gHMBC spectra. For the first time, the spin-lattice relaxation time (T1) of protons of the chain-ends is revealed to be affected more by polymer molecular weight (MW) than by the protons of the main-chains and the side-chains (almost independent from MW). As a result, a much higher delay time (d1) for chain-ends (d1 > 20T1) is needed for quantitative NMR measurement when using end-group estimation method to obtain the MW of PS, which is in accordance with the value estimated by GPC. An improved method for the polymer MW determination is established, by combination of different NMR techniques to distinguish the peaks, and a large d1 setting to achieve quantitative NMR analysis.
Co-reporter:Minzhi Zhang, Jiali Gu, Xiang Zhu, Lingfeng Gao, Xiaohong Li, Xiaoming Yang, Yingfeng Tu, Christopher Y. Li
Polymer 2017 Volume 130(Volume 130) pp:
Publication Date(Web):9 November 2017
DOI:10.1016/j.polymer.2017.10.010
•Double crystalline multiblock terpolymers have been synthesized by a PROP method.•The confinement crystallization behavior was observed in these multiblock terpolymers.•These multiblock terpolymers show interesting microphase separation morphologies.We present here the application of in situ cascade polycondensation-coupling ring-opening polymerization (PROP) method for the facile synthesis of a series of three-component poly(butylene terephthalate)-block-poly(ethylene oxide)-block-poly(propylene oxide)-block-poly(ethylene oxide) multiblock terpolymers (PBT-b-PEO-b-PPO-b-PEO-b-PBT)n, using cyclic oligo(butylene terephthalate)s (COBTs) as monomers and dihydroxyl end-functional PEO-b-PPO-b-PEO (EPE) as macroinitiator. The structure details of these copolymers were characterized by 1H-1H gCOSY and 1H-13C gHSQC NMR spectra. With the assignment of multiblock chain ends, block segmental ends and corresponding groups for each segment, the number-average molecular weights for multiblock terpolymers and each block segment were estimated by the quantitative 1H NMR spectra. Polymerization kinetics studies confirm the PROP mechanism. With crystalline PBT and PEO segments, the multiblock terpolymers are double-crystalline polymers, where the melting point and crystallinity of PBT and PEO segments increase with corresponding PBT and PEO content, respectively. The covalent linking of PBT segments with PEO segments leads to the confined crystallization environment for both blocks, where a strong depression on melting point of PEO crystals was observed, which becomes amorphous at an EPE triblock content of 50%. TEM and SAXS results show interesting lamella-like microphase separation morphologies in these multiblock terpolymers.Download high-res image (292KB)Download full-size image
Co-reporter:Jianying Chen, Dongxue Chen, Weichun Huang, Xiaoming Yang, Xiaohong Li, Yingfeng Tu, Xiulin Zhu
Polymer 2016 Volume 107() pp:29-36
Publication Date(Web):19 December 2016
DOI:10.1016/j.polymer.2016.11.001
•A polycondensation-coupling ring-opening polymerization (PROP) method is developed.•(PBT-b-PTMO-b-PBT)n multiblock copolymers were synthesized by the PROP method.•The multiblock copolymers show better thermal stability than PTMO homopolymers.A novel polycondensation-coupling ring-opening polymerization (PROP) method is utilized to synthesize poly(butylene terephthalate)-block-poly(tetramethylene oxide) alternative multiblock copolymers (PBT-b-PTMO-b-PBT)nvia the one pot melt polymerization of cyclic oligo(butylene terephthalate)s (COBTs) and dihydroxy end-functional PTMO (macroinitiator). The proton peaks in 1H NMR spectra corresponding to each block segments, the segmental ends connecting with different blocks, and copolymer chain ends, are assigned by the 1H-1H gCOSY 2D NMR spectra, respectively. The number-average molecular weights of multiblock copolymers and each segment are revealed by an improved quantitative 1H NMR spectra. The results show the molecular weights of the multiblock copolymers increase linearly with reaction time, while the molecular weights for each block segment remain the same, following the PROP mechanism, i.e., the ring-opening polymerization of COBTs by PTMO macroinitiator to form PBT-b-PTMO-b-PBT triblock copolymers at the first stage (short and quickly), then coupling with the condensation polymerization of triblock copolymers to form (PBT-b-PTMO-b-PBT)n alternative multiblock copolymers at the second stage. The mechanism is also supported by GPC results. These multiblock copolymers show improved thermal stability compared with PTMO homopolymers.
Co-reporter:Lingfeng Gao, Joongsuk Oh, Taihyun Chang, Dongxue Chen, Xiaohong Li, Xiaoming Yang, Yingfeng Tu, Xiulin Zhu, Christopher Y. Li
Polymer 2016 Volume 101() pp:379-387
Publication Date(Web):28 September 2016
DOI:10.1016/j.polymer.2016.08.086
•Optimum cyclization conditions for the synthesis of high purity c-PS are revealed.•The effect of molecular weight, concentration and solvent is systematically studied.•The cyclization yield is greatly affected by the polymer chain conformation.We report herein the effects of solvent, concentration, and molecular weight of α-alkynyl-ω-azido polystyrenes (l-PS-N3) on the synthesis of monocyclic polystyrenes (c-PS) by intra-chain coupling of l-PS-N3via Cu-catalyzed azide/alkyne cycloaddition method. By using fully end-functionalized l-PS-N3 as precursors, the optimum cyclization conditions to synthesize high purity c-PS (>99% by SEC) are revealed, at concentrations around 7.9 μmol/L in DMF. The c-PS products are fully characterized by SEC, LCCC, 1H NMR, and MALDI-TOF Mass spectrometry. The yield of c-PS decreases with increment of concentration of l-PS-N3 as predicted by Jacobson and Stockmayer's equation. Interestingly, among the three studied PS samples with different molecular weight (∼4k, 9k, 14k Da), the medium one (PS9k) provides the best c-PS yield, while in the three studied solvent (toluene, DMF, cyclohexane), DMF gives the best yied. The results reveal that the PS chain conformation in the solution, which is affected by the solvent and molecular weights, plays an important role in the intra-chain cyclization reaction.
Co-reporter:Liangliang Ji, Xiaofang Chen, Yanhong Wu, Xiaoming Yang, Yingfeng Tu
Polymer 2015 Volume 61() pp:147-154
Publication Date(Web):20 March 2015
DOI:10.1016/j.polymer.2015.01.077
•Different morphologies are observed in the liquid crystalline block copolymers.•In major LC block weight fraction range, lamella morphology dominates.Order-order transition and lamella to modified layer structure change were observed.A series of narrowly distributed diblock copolymers composed of amorphous components and side-chain liquid crystalline (LC) polymer, poly (butyl acrylate)-block-poly [8-(4-cyano-4′-biphenyl)-1-octanoyl acrylate] (PBA-b-PCBOA), with side-chain LC block weight fraction (fw,PCBOA) ranging from 25% to 87%, were synthesized by atom transfer radical polymerization (ATRP). Their thermal property, LC behavior, bulk phase behavior and thin film morphology were studied by differential scanning calorimetry (DSC), polarizing optical microscope (POM), small-angle X-ray scattering (SAXS) techniques and atomic force microscopy (AFM), respectively. The results show the diblock copolymers with different composition could present sphere, lamellar and cylinder morphologies before the order–disorder transition. As the mesogen units self-organize to form smectic phase, the lamellar morphology dominates during the majority LC block weight fraction range (fw,PCBOA = 46%–77%) to minimized the surface energy. Interestingly, for spin-coated thin film, the lamella phase separation size decreased with increasing annealing time. For the copolymer with fw,PCBOA of 67%, a thermoreversible order–order transition (OOT) and lamella to lamella/modified layer (L/ML), were observed.
Co-reporter:Jun Wu;Tao-guang Qu;Ling-feng Gao;Xiao-ming Yang
Chinese Journal of Polymer Science 2015 Volume 33( Issue 8) pp:1069-1073
Publication Date(Web):2015 August
DOI:10.1007/s10118-015-1675-2
We demonstrate here seven pure cyclic samples, which belongs to two series of oligoesters, cyclic oligo(trimethylene terephthalate)s (COTTs) and cyclic oligo(butylene terephthalate)s (COBTs), showing odd-even effect of degree of oligomerization (repeating units number) on properties. The pentamer of COTT and trimer of COBT show much lower melting temperature, and the trimer of COTT and trimer of COBT show significant lower refractive index, which can be ascribed to the low packing density of cyclic oligoesters with odd number of degree of oligomerization. Our results reveal the discrete property change as a function of cyclic size of oligomers, which can be used to design materials with special properties.
Co-reporter:Shuang Chen, Dongxue Chen, Min Lu, Xin Zhang, He Li, Xiaoyan Zhang, Xiaoming Yang, Xiaohong Li, Yingfeng Tu, and Christopher Y. Li
Macromolecules 2015 Volume 48(Issue 23) pp:8480-8488
Publication Date(Web):November 20, 2015
DOI:10.1021/acs.macromol.5b01791
To achieve high refractive index polymers (HRIPs), we report here the design and synthesis of four fullerene polyesters (P1–P4), based on the conjunction effect from the high refractive index polyester backbones and pendent fullerene side chains. At sodium D line (589 nm), the refractive indices of the fullerene polyesters are all higher than 1.80, the used believed upper limitation of intrinsic organic polymers. To achieve precise pendent fullerene structure, these polyesters were synthesized via condensation polymerization by a fullerene diol with different aromatic diacyl chlorides, where the diacyl chlorides with high molar refraction increment value moiety were selected by molecular tailoring according to Lorentz–Lorenz equation. The fullerene polyesters are characterized by gel permeation chromatography (GPC), ultraviolet–visible (UV–vis) spectroscopy, and the molecular weights are obtained by a quantitative NMR technique with end-group estimation. The formation of fullerene polyesters is also proved by the 1H DOSY NMR results. These fullerene polyesters have good solubility in some common organic solvents, good thermal stability up to 320 °C, and film forming ability. All these films have good adhesion to glass sheets with relatively good hardness. Among them, the thiophene-containing fullerene polyesters (P1) has the best optical properties, with the highest refractive index value (1.86 at 589 nm), one of the highest value for intrinsic organic polymers, and the highest Abbe number (27.9).
Co-reporter:Xiaoyan Zhang;Dr. Chih-Hao Hsu;Dr. Xiangkui Ren;Yan Gu; Bo Song;Dr. Hao-Jan Sun; Shuang Yang; Erqiang Chen; Yingfeng Tu; Xiaohong Li; Xiaoming Yang; Yaowen Li; Xiulin Zhu
Angewandte Chemie International Edition 2015 Volume 54( Issue 1) pp:114-117
Publication Date(Web):
DOI:10.1002/anie.201408438
Abstract
Fullerene-based liquid crystalline materials have both the excellent optical and electrical properties of fullerene and the self-organization and external-field-responsive properties of liquid crystals (LCs). Herein, we demonstrate a new family of thermotropic [60]fullerene supramolecular LCs with hierarchical structures. The [60]fullerene dyads undergo self-organization driven by π–π interactions to form triple-layer two-dimensional (2D) fullerene crystals sandwiched between layers of alkyl chains. The lamellar packing of 2D crystals gives rise to the formation of supramolecular LCs. This design strategy should be applicable to other molecules and lead to an enlarged family of 2D crystals and supramolecular liquid crystals.
Co-reporter:Xiaoyan Zhang;Dr. Chih-Hao Hsu;Dr. Xiangkui Ren;Yan Gu; Bo Song;Dr. Hao-Jan Sun; Shuang Yang; Erqiang Chen; Yingfeng Tu; Xiaohong Li; Xiaoming Yang; Yaowen Li; Xiulin Zhu
Angewandte Chemie 2015 Volume 127( Issue 1) pp:116-119
Publication Date(Web):
DOI:10.1002/ange.201408438
Abstract
Fullerene-based liquid crystalline materials have both the excellent optical and electrical properties of fullerene and the self-organization and external-field-responsive properties of liquid crystals (LCs). Herein, we demonstrate a new family of thermotropic [60]fullerene supramolecular LCs with hierarchical structures. The [60]fullerene dyads undergo self-organization driven by π–π interactions to form triple-layer two-dimensional (2D) fullerene crystals sandwiched between layers of alkyl chains. The lamellar packing of 2D crystals gives rise to the formation of supramolecular LCs. This design strategy should be applicable to other molecules and lead to an enlarged family of 2D crystals and supramolecular liquid crystals.
Co-reporter:Honghong Yan, Shuang Chen, Min Lu, Xiang Zhu, Yanqing Li, Dezhen Wu, Yingfeng Tu and Xiulin Zhu
Materials Horizons 2014 vol. 1(Issue 2) pp:247-250
Publication Date(Web):17 Jan 2014
DOI:10.1039/C3MH00105A
By introducing flexible spacers between pendant fullerenes and the backbone, side-chain fullerene polyesters with high fullerene content and good solubility were synthesized by condensation polymerization. These polyesters are a new class of soluble high refractive index polymers (HRIPs) with the highest value of 1.79 at the sodium D line (589 nm).
Co-reporter:Yingfeng Tu;Zhichao Ji;Xiaoming Yang;Xinhua Wan;Qi-Feng Zhou
Macromolecular Rapid Communications 2014 Volume 35( Issue 20) pp:1795-1800
Publication Date(Web):
DOI:10.1002/marc.201400381
Co-reporter:Chao Li, Xiaoming Yang, Yue Zhao, Pan Zhang, Yingfeng Tu, Yaowen Li
Organic Electronics 2014 Volume 15(Issue 11) pp:2868-2875
Publication Date(Web):November 2014
DOI:10.1016/j.orgel.2014.08.007
•Well defined graphene oxide (pr-GOs) were successfully synthesized and applied in OSCs.•The pr-GOs as hole extraction layer (HEL) possessing controllable multiple functionalities.•Dependence between device performance and multiple functionalities of pr-GOs as HEL.•pr-GO-3 exhibited superior device efficiency, stability, and repeatability as compared with PEDOT:PSS.A simple method for synthesizing a series of graphene oxide with precise oxidation (pr-GO) (mild oxidation, moderate oxidation and severe oxidation) by strictly controlling pre-oxidation steps, oxidant content and oxidation time has been successfully developed. The well defined pr-GO as hole extraction layer (HEL) presented multiple functionalities, like modulation of work function, enhanced interfacial dipole, and excellent film-forming properties, which had significantly improved the efficiency and stability of organic solar cells. The P3HT:PC61BM system device based on pr-GO-3 HEL, which possessing well defined electronic structure and moderate oxidation, exhibited an improved 3.74% in power conversion efficiency and better air-stability compared to that of other pr-GOs and conventional PEDOT:PSS based devices. The well defined electronic structure pr-GO (i.e., suitable work function, larger interfacial dipole, and high repeatability) will provide better understanding in utilizing pr-GO film as HEL in future solar cell applications.A simple method for synthesizing a series of graphene oxide with precise oxidation (pr-GO) (mild oxidation, moderate oxidation and severe oxidation) has been successfully developed. pr-GOs present multiple functionalities which is an excellent hole extraction material. Moderate oxidated pr-GO-3 as hole extraction layer (HEL) exhibited an improved 3.74% in power conversion efficiency and better air-stability compared to devices with other pr-GOs and conventional PEDOT:PSS HEL.
Co-reporter:Chengxin Guo;Liangliang Ji;Yaowen Li;Xiaoming Yang
Journal of Applied Polymer Science 2014 Volume 131( Issue 11) pp:
Publication Date(Web):
DOI:10.1002/app.40332
ABSTRACT
Two types of graphene oxide (GO) powders were prepared by freeze-drying or spray-drying method, and their composites with poly(trimethylene terephthalate) (PTT) were prepared by melt blending. The influence of GO powders' type and content on crystallization behavior of PTT was investigated by differential scanning calorimeter (DSC) and polarized optical microscopy (POM). DSC results indicated that the overall crystallization rate of PTT was accelerated by well-dispersed GO material which acts as a heterogeneous nucleation agent, since the Avrami parameter obtained is near 3. On the contrary, large GO aggregates which is in the minority will hinder the nucleation. Interestingly, large and well-defined PTT spherulites instead of tremendous stunted spherulites were observed from POM, which means only a small portion of GO powders was acted as nucleation agent. Meanwhile, GO powders had no effect on PTT spherulites growth rate. In addition, the band spacing of PTT spherulites became weaker and wider with increasing GO content. © 2014 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2014, 131, 40332.
Co-reporter:Weichun Huang, Sheng Wang, Chengxin Guo, Xiaoming Yang, Yaowen Li, Yingfeng Tu
Polymer 2014 Volume 55(Issue 18) pp:4619-4626
Publication Date(Web):2 September 2014
DOI:10.1016/j.polymer.2014.07.014
Two simple and effective methods, “click” chemistry and supramolecular interactions, are demonstrated here to synthesize well-defined poly(l-lactide) (PLLA) functionalized graphene oxide (GO) sheets. We provide a simple method to introduce azide groups on GO sheets by the ring opening reaction of sodium azide with the epoxide groups of GO. The GO-N3 sheets can easily undergo “click” reaction with alkyne-terminated PLLA by “grafting onto” method to produce GO/PLLA composites with high grafting ratio and exfoliated structure. Interestingly, GO-N3 can be grafted with oxygen-containing polymers such as PLLA, polymethyl methacrylate (PMMA) or polyethylene oxide (PEO) via supramolecular interactions between the azide groups and these oxygen atoms on polymers, producing GO/polymer composites with low grafting ratio and intercalated structure. These “grafting onto” methods are useful to produce a variety of GO/polymer composites with different structure via “click” reaction or supramolecular interactions, which have potential applications in material science.
Co-reporter:Chao Li, Yujin Chen, Yue Zhao, Huifang Wang, Wei Zhang, Yaowen Li, Xiaoming Yang, Changqi Ma, Liwei Chen, Xiulin Zhu and Yingfeng Tu
Nanoscale 2013 vol. 5(Issue 20) pp:9536-9540
Publication Date(Web):08 Aug 2013
DOI:10.1039/C3NR03048B
A series of acceptor–donor–acceptor-based small molecules (SMs) with varied crystallinity were successfully synthesized. The processing additive can induce the SMs to self-organize as nanofibrils with higher crystallinity and controlled scales of nanofibrils, which have significant influence on the photovoltaic performance.
Co-reporter:Pan Zhang, Chao Li, Yaowen Li, Xiaoming Yang, Liwei Chen, Bin Xu, Wenjing Tian and Yingfeng Tu
Chemical Communications 2013 vol. 49(Issue 43) pp:4917-4919
Publication Date(Web):08 Apr 2013
DOI:10.1039/C3CC41321G
A bulk tri(octyloxy)benzene moiety grafted onto fullerene (PCBB-C8) was successfully synthesized, which could effectively induce poly(3-hexylthiophene) (P3HT) to form highly ordered bulk heterojunction structure without any external treatment. This ordered active layer exhibits good photovoltaic performance.
Co-reporter:Lijun Ma, Xiaoming Yang, Lingfeng Gao, Min Lu, Chengxin Guo, Yaowen Li, Yingfeng Tu, Xiulin Zhu
Carbon 2013 Volume 53() pp:269-276
Publication Date(Web):March 2013
DOI:10.1016/j.carbon.2012.10.058
We provide here a simple way to synthesize polymer grafted graphene oxide (GO) sheets with intercalated or exfoliated structure by using a redox system with cerium (IV) ammonium nitrate/nitric acid and GO sheets’ hydroxyl groups as the redox couple. Polystyrene, poly (methyl methacrylate) and polyacrylonitrile grafted GO sheets were synthesized in an aqueous solution by this redox-initiated free-radical polymerization strategy, and characterized with Fourier transform infrared spectroscopy, X-ray diffraction, and atomic force microscopy. We investigated the effects of temperature and redox initiator’s concentration on the grafting efficiency. It was found that when a small amount of polymer was grafted onto GO sheets, an intercalated layer structure was formed; while an exfoliated structure was formed with a large amount of polymer grafted.
Co-reporter:Yujin Chen, Chao Li, Pan Zhang, Yaowen Li, Xiaoming Yang, Liwei Chen, Yingfeng Tu
Organic Electronics 2013 Volume 14(Issue 5) pp:1424-1434
Publication Date(Web):May 2013
DOI:10.1016/j.orgel.2013.02.038
•Narrow band gap molecule can be obtained by tuning central units in A–D–A structure.•Small molecule with a mediated oligothiophene conjugated length exhibits higher crystallinity and more ordered structure.•Higher crystallization molecule showed better power conversion efficiency.•The optimized TT(HTTzHT)2:PC71BM based device exhibit a high PCE of 3.24% in OSCs.A series of high coplanar alternative linear small molecules with acceptor–donor–acceptor (A–D–A) structure containing electron-accepting tetrazine (Tz) moiety and electron-donating oligothiophenes (OTs) moiety, alkylated thiophene attached to both sides of the Tz moiety were designed and synthesized. The influences of varied oligothiophene length on small molecules’ optical and electrochemical properties, crystallization, self assembling morphology in blend film with (6,6)-phenyl-C61-butyric acid methyl ester (PC61BM), and photovoltaic properties for the application as donor materials in organic solar cells (OSCs) were studied. The optical and electrochemical properties of small molecules showed that the HOMO and LUMO energy levels were determined by the number of OTs moiety and electron-accepting ability of Tz in the alternative small molecules, respectively. Meanwhile, the varied OT moieties can significantly affect the hierarchical structures when mixed with PC61BM. The molecule with intermediate conjugate moity length showed the highest ordering in its crystalline state, as revealed by differential scanning calorimetry (DSC) and X-ray diffraction experiments, and best photovoltaic properties when blended together with PC61BM or (6,6)-phenyl-C71-butyric acid methyl ester (PC71BM) as active layer in photovoltaic devices. The results indicate that hierarchical structures controlled by adjusting the conjugate moity length of small molecules is an effective way to improve the performance of OSCs. The photovoltaic device based on TT(HTTzHT)2:PC71BM with 1% DIO additives showed the best performance, with a Jsc of 7.87 mA/cm2 and a PCE of 3.24%.A series of high coplanar alternative linear small molecules with acceptor–donor–acceptor (A–D–A) structure containing electron-accepting tetrazine moiety and electron-donating olighothiophenes (OTs) moiety, alkylated thiophene attached to both sides of the Tz moiety were designed and synthesized. The influences of varied oligothiophene length on small molecules’ optical and electrochemical properties, crystallization, hierarchical structure in blend film with (6,6)-phenyl-C61-butyric acid methyl ester, and photovoltaic properties for the application as donor materials in organic solar cells were studied. The hierarchical structure can be tuned by changing the OTs based on the A–D–A structure, which exhibit great effect on the photovoltaic properties.
Co-reporter:Pan Zhang;Chao Li;Yue Zhao;Yaowen Li
Chinese Journal of Chemistry 2013 Volume 31( Issue 11) pp:1439-1448
Publication Date(Web):
DOI:10.1002/cjoc.201300512
Abstract
A series of acceptor-donor-acceptor alternative small molecules were synthesized containing electron-donating central building moieties of phenothiazine, 2,7-carbazole and thieno[3,4-b]thiophene and electron-accepting moieties of tetrazine on both sides. The various conformations of the central blocks, with the coplanarity in an order of phenothiazine<2,7-carbazole<thieno[3,4-b]thiophene, have an obvious influence on the optical, electrochemical property and the crystallinity of small molecule. In addition, the blend films between small molecule and (6,6)-phenyl-C61-butyric acid methyl ester offered signi?cantly various morphologies, changing from uniform surface to interpenetrated networks. As a result, the bulk heterojunction photovoltaic devices based on the three small molecules provided varied performance, and the highest coplanar molecule based device exhibited the best photovoltaic performance.
Co-reporter:Xiaoming Yang, Chengxin Guo, Liangliang Ji, Yaowen Li, and Yingfeng Tu
Langmuir 2013 Volume 29(Issue 25) pp:8103-8107
Publication Date(Web):May 27, 2013
DOI:10.1021/la401038c
We demonstrated here the lyotropic liquid crystalline behavior of an aqueous solution of graphene oxide (GO) sheets. Scanning electron microscope experiments revealed GO sheets self-assembled into fiber-like or sheet-like structures at different concentrations under flow conditions. As a result, the solution viscosity decreased dramatically with increasing shear stress.
Co-reporter:Qiaozhen Xu, Jianying Chen, Weichun Huang, Taoguang Qu, Xiaohong Li, Yaowen Li, Xiaoming Yang, and Yingfeng Tu
Macromolecules 2013 Volume 46(Issue 18) pp:7274-7281
Publication Date(Web):September 11, 2013
DOI:10.1021/ma400969a
We present here the one pot, one step synthesis of poly(trimethylene terephthalate)-block-poly(tetramethylene oxide) multiblock copolymers (PTT-b-PTMO-b-PTT)n by melt polymerization of cyclic oligo(trimethylene terephthalate)s (COTTs) with PTMO macroinitiator. An improved quantitative 1H NMR characterization technique was developed and applied to investigate the multiblock copolymers’ structure with different reaction time by the chain end and functional groups estimation. The polymerization kinetics was revealed, and the results indicated a two-stage polymerization mechanism: melt ring-opening polymerization of cyclic oligo(trimethylene terephthalate)s (COTTs) by PTMO macroinitiator to form triblock copolymers at first stage, followed by the in-situ condensation polymerization of block copolymers to produce multiblock copolymers at second stage. This was further confirmed by the gel permeation chromatography (GPC) and viscosity experiments. To our knowledge, this is the first reported poly(ether ester) multiblock copolymers synthesized by one step polymerization process and with controlled structures. These multiblock copolymers show good thermal stability and double crystalline properties.
Co-reporter:Jianying Chen, Weichun Huang, Qiaozhen Xu, Yingfeng Tu, Xiulin Zhu, Erqiang Chen
Polymer 2013 Volume 54(Issue 25) pp:6725-6731
Publication Date(Web):27 November 2013
DOI:10.1016/j.polymer.2013.10.043
We demonstrated here a facile method to synthesize novel double crystalline poly(butylene terephthalate)-block-poly(ethylene oxide)-block-poly(butylene terephthalate) (PBT-b-PEO-b-PBT) triblock copolymers by solution ring-opening polymerization (ROP) of cyclic oligo(butylene terephthalate)s (COBTs) using poly(ethylene glycol) (PEG) as macroinitiator and titanium isopropyloxide as catalyst. The structure of copolymers was well characterized by 1H NMR and GPC. TGA results revealed that the decomposition temperature of PEO in triblock copolymers increased about 30 °C to the same as PBT copolymers, after being end-capped with PBT polymers. These triblock copolymers showed double crystalline properties from PBT and PEO blocks, observed from DSC and WAXD measurements. The melting and crystallization peak temperatures corresponding to PBT blocks increased with PBT content. The crystallization of PBT blocks showed the strong confinement effects on PEO blocks due to covalent linking of PBT blocks with PEO blocks, where the melting and crystallization temperatures and crystallinity corresponding to PEO blocks decreased significantly with increment of PBT content. The confinement effect was also observed by SAXS experiments, where the long distance order between lamella crystals decreases with increasing PBT length. For the triblock copolymer with highest PBT content (PBT54-b-PEO227-b-PBT54), this effect shows a 30 °C depression on PEO crystals' melting temperature and 77% on enthalpy, respectively, compared to corresponding PEO homopolymer. The crystal morphology was observed by POM, and amorphous-like spherulites were observed during PBT crystallization.
Co-reporter:Li Yaowen, Liwei Chen, Yujin Chen, Chao Li, Pan Zhang, Lingfeng Gao, Xiaoming Yang, Yingfeng Tu, Xiulin Zhu
Solar Energy Materials and Solar Cells 2013 108() pp: 136-145
Publication Date(Web):
DOI:10.1016/j.solmat.2012.09.023
Co-reporter:Hao-Jan Sun, Yingfeng Tu, Chien-Lung Wang, Ryan M. Van Horn, Chi-Chun Tsai, Matthew J. Graham, Bin Sun, Bernard Lotz, Wen-Bin Zhang and Stephen Z. D. Cheng
Journal of Materials Chemistry A 2011 vol. 21(Issue 37) pp:14240-14247
Publication Date(Web):14 May 2011
DOI:10.1039/C1JM10954E
A shape amphiphile composed of covalently linked spherical and cubic nanoparticles with distinct symmetry ([60]fullerene (C60) and polyhedral oligomeric silsesquioxane (POSS)) was synthesized and its solid state structures were characterized. The two types of nanoparticles are known to be generally immiscible, but they were connected with a short covalent linkage forming an organic–inorganic dyad (POSS–C60) which exhibited interesting crystallization characteristics. Crystals of the dyad exhibited polymorphism with two different crystal structures: an orthorhombic and a hexagonal unit cell with symmetry groups of P21212 and P6, respectively, both of which formed an alternating bi-layered structure of POSS and C60. The different symmetry groups in the polymorphs were attributed to the different packing orientations of the POSS within each layer. In the orthorhombic unit cell, one set of the edges of the POSS moieties is parallel to the c-axis; while in the hexagonal unit cells the body-diagonal is parallel to the c-axis of the crystal. Based on the crystal packing structure and density differential, it has been determined that the hexagonal unit cell structure is the more thermodynamically stable phase. This type of bi-layered structure with an alternating conductive fullerene and insulating POSS layer structure is of great interest for various potential applications such as nano-capacitors.
Co-reporter:Xiaoming Yang, Lijun Ma, Sheng Wang, Yaowen Li, Yingfeng Tu, Xiulin Zhu
Polymer 2011 Volume 52(Issue 14) pp:3046-3052
Publication Date(Web):22 June 2011
DOI:10.1016/j.polymer.2011.04.062
Polystyrene (PS) graft graphite oxide (GO) was synthesized by Cu (I)-catalyzed 1, 3-dipolar cycloaddition (“click” coupling) of azido modified graphite oxide with well-defined, alkyne-terminated polystyrene. This method produced PS blocks graft on GO surface, while ordered layer structure between GO sheets was observed for the first time in GO/Polymer composite. The layered structure was characterized and confirmed by 1D X-ray diffraction (XRD) and atomic force microscopy (AFM), and the layer thickness was observed to be controlled with intercalated PS length between GO layers.
Co-reporter:Yaowen Li, Yujin Chen, Xing Liu, Zhong Wang, Xiaoming Yang, Yingfeng Tu, and Xiulin Zhu
Macromolecules 2011 Volume 44(Issue 16) pp:6370-6381
Publication Date(Web):August 2, 2011
DOI:10.1021/ma201009n
A series of varied length alkyl substituted donor–acceptor (D–A) conjugated copolymers with benzo[1,2-b:4,5-b′]dithiophene (BDT) as donor and thiophene rings attached to both sides of the benzothiadiazole (TBT) moieties as acceptors were designed and synthesized. The optical and electrochemical properties showed that the absorption spectrum, the band gaps, and the energy levels of the copolymers were not affected by the varied substituted alkyls, and all these copolymers showed low band gaps around 1.75 eV. In addition, the morphologies of the blend film between copolymers and PCBM can be fine-tuned by increasing the length of substituted alkyl of the copolymers, changing from pea-like aggregation to interpenetrating network to grain-like aggregation. Bulk heterojunction photovoltaic devices were fabricated by using the copolymers as donors and (6,6)-phenyl C61-butyric acid methyl ester (PC61BM) or (6,6)-phenyl C71-butyric acid methyl ester (PC71BM) as acceptors. The optimized photovoltaic performances showed the stable open-circuit voltage (Voc) in the range of 0.68 to 0.74 eV, and dramatically increasing short circuit current density (Jsc) by optimizing the blending morphologies of copolymer and PCBM films. The optimized photovoltaic performance with a Voc of 0.70 V, Jsc of 7.19 mA/cm2, a fill factor (FF) of 0.52, and a power conversion efficiency (PCE) of 2.88%, was obtained by the copolymer PBDT-TBT-C8 (PBDT-TBT-C8:PC61BM, 1:3 w/w, in CB solution). This is due to its low band gap and interpenetrating network morphology of PBDT-TBT-C8:PC61BM blend film. The photovoltaic device based on PBDT-TBT-C8:PC71BM showed a Jsc of 8.6 mA/cm2 and a PCE of 3.15%.
Co-reporter:YingFeng Tu;ZhenPing Cheng;ZhengBiao Zhang;Jian Zhu
Science China Chemistry 2010 Volume 53( Issue 8) pp:1605-1619
Publication Date(Web):2010 August
DOI:10.1007/s11426-010-4051-7
This tutorial review summarizes recent progress in the research field of controlled/“living” radical polymerization (CLRP) from Soochow University. The present paper gives a broad overview of the mechanism study and molecular design in CLRP. The mechanism study in CLRP aided by microwave, initiated by γ-radiation at low temperature, mediated by iron, in reversible addition-fragmentation chain transfer (RAFT) polymerization and the mechanism transfer between different CLRP processes are reviewed and summarized. The molecular design in CLRP, especially in RAFT polymerization for mechanism study, and in achieving tailor-made functional polymers is studied and discussed in the later part.
Co-reporter:Tiantian Zhu, Xiaoyan Zhang, Zhikai Li, Chih-Hao Hsu, Wei Chen, Toshikazu Miyoshi, Xiaohong Li, Xiaoming Yang, Yingfeng Tu and Christopher Y. Li
Chemical Communications 2017 - vol. 53(Issue 59) pp:NaN8339-8339
Publication Date(Web):2017/06/30
DOI:10.1039/C7CC03195E
We present here that in two-dimensional (2D) fullerene supramolecular liquid crystals (SLCs), the phase diagram and lamella thickness of SLCs and 2D crystals can be tuned by the flexible alkyl tail and spacer length, due to their different effects on enthalpy and entropy changes during SLC formation.
Co-reporter:Pan Zhang, Chao Li, Yaowen Li, Xiaoming Yang, Liwei Chen, Bin Xu, Wenjing Tian and Yingfeng Tu
Chemical Communications 2013 - vol. 49(Issue 43) pp:NaN4919-4919
Publication Date(Web):2013/04/08
DOI:10.1039/C3CC41321G
A bulk tri(octyloxy)benzene moiety grafted onto fullerene (PCBB-C8) was successfully synthesized, which could effectively induce poly(3-hexylthiophene) (P3HT) to form highly ordered bulk heterojunction structure without any external treatment. This ordered active layer exhibits good photovoltaic performance.
Co-reporter:Hao-Jan Sun, Yingfeng Tu, Chien-Lung Wang, Ryan M. Van Horn, Chi-Chun Tsai, Matthew J. Graham, Bin Sun, Bernard Lotz, Wen-Bin Zhang and Stephen Z. D. Cheng
Journal of Materials Chemistry A 2011 - vol. 21(Issue 37) pp:NaN14247-14247
Publication Date(Web):2011/05/14
DOI:10.1039/C1JM10954E
A shape amphiphile composed of covalently linked spherical and cubic nanoparticles with distinct symmetry ([60]fullerene (C60) and polyhedral oligomeric silsesquioxane (POSS)) was synthesized and its solid state structures were characterized. The two types of nanoparticles are known to be generally immiscible, but they were connected with a short covalent linkage forming an organic–inorganic dyad (POSS–C60) which exhibited interesting crystallization characteristics. Crystals of the dyad exhibited polymorphism with two different crystal structures: an orthorhombic and a hexagonal unit cell with symmetry groups of P21212 and P6, respectively, both of which formed an alternating bi-layered structure of POSS and C60. The different symmetry groups in the polymorphs were attributed to the different packing orientations of the POSS within each layer. In the orthorhombic unit cell, one set of the edges of the POSS moieties is parallel to the c-axis; while in the hexagonal unit cells the body-diagonal is parallel to the c-axis of the crystal. Based on the crystal packing structure and density differential, it has been determined that the hexagonal unit cell structure is the more thermodynamically stable phase. This type of bi-layered structure with an alternating conductive fullerene and insulating POSS layer structure is of great interest for various potential applications such as nano-capacitors.
![3'H-Cyclopropa[1,9][5,6]fullerene-C60-Ih-3'-carboxylic acid, 9-[1-[6-[3,5-bis(hydroxymethyl)phenoxy]hexyl]-1H-1,2,3-triazol-4-yl]nonyl ester](/data/chemimg/3781700/1523249-03-7.png)
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![3'H-Cyclopropa[1,9][5,6]fullerene-C60-Ih-3'-carboxylic acid, 8-[[3,4,5-tris(dodecyloxy)benzoyl]oxy]octyl ester](/data/chemimg/3781700/1644178-86-8.png)
![3'H-Cyclopropa[1,9][5,6]fullerene-C60-Ih-3'-carboxylic acid, 8-[[3,4,5-tris(dodecyloxy)benzoyl]oxy]octyl ester](/data/chemimg/3781700/1644178-86-8_b.png)
![3'H-Cyclopropa[1,9][5,6]fullerene-C60-Ih-3'-carboxylic acid, 8-[[3,4,5-tris(decyloxy)benzoyl]oxy]octyl ester](/data/chemimg/3781700/1644178-87-9.png)
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![3'H-Cyclopropa[1,9][5,6]fullerene-C60-Ih-3'-carboxylic acid, 10-undecyn-1-yl ester](/data/chemimg/3781700/1523249-01-5.png)
![3'H-Cyclopropa[1,9][5,6]fullerene-C60-Ih-3'-carboxylic acid, 10-undecyn-1-yl ester](/data/chemimg/3781700/1523249-01-5_b.png)
![Pentanoic acid, 4-cyano-4-[(phenylthioxomethyl)thio]-, 2-propyn-1-yl ester](/data/chemimg/190000/1075252-15-1.png)
![Pentanoic acid, 4-cyano-4-[(phenylthioxomethyl)thio]-, 2-propyn-1-yl ester](/data/chemimg/190000/1075252-15-1_b.png)
![2-Propenoic acid, 8-[(4'-cyano[1,1'-biphenyl]-4-yl)oxy]octyl ester](/data/chemimg/3041200/189498-10-0.png)
![2-Propenoic acid, 8-[(4'-cyano[1,1'-biphenyl]-4-yl)oxy]octyl ester](/data/chemimg/3041200/189498-10-0_b.png)
![2,1,3-Benzothiadiazole, 4,7-bis(5-bromo-6-pentylthieno[3,2-b]thien-2-yl)-5,6-bis(octyloxy)-, polymer with 1,1'-[4,8-bis(dodecyloxy)benzo[1,2-b:4,5-b']dithiophene-2,6-diyl]bis[1,1,1-trimethylstannane]](/data/chemimg/3778200/1472641-56-7.png)
![2,1,3-Benzothiadiazole, 4,7-bis(5-bromo-6-pentylthieno[3,2-b]thien-2-yl)-5,6-bis(octyloxy)-, polymer with 1,1'-[4,8-bis(dodecyloxy)benzo[1,2-b:4,5-b']dithiophene-2,6-diyl]bis[1,1,1-trimethylstannane]](/data/chemimg/3778200/1472641-56-7_b.png)
![2,1,3-Benzothiadiazole, 4,7-dibromo-5,6-bis(octyloxy)-, polymer with 1,1'-[4,8-bis(dodecyloxy)benzo[1,2-b:4,5-b']dithiophene-2,6-diyl]bis[1,1,1-trimethylstannane]](/data/chemimg/3778200/1472641-55-6.png)
![2,1,3-Benzothiadiazole, 4,7-dibromo-5,6-bis(octyloxy)-, polymer with 1,1'-[4,8-bis(dodecyloxy)benzo[1,2-b:4,5-b']dithiophene-2,6-diyl]bis[1,1,1-trimethylstannane]](/data/chemimg/3778200/1472641-55-6_b.png)
![Stannane, 1,1'-[4,8-bis(dodecyloxy)benzo[1,2-b:4,5-b']dithiophene-2,6-diyl]bis[1,1,1-trimethyl-, polymer with 2,5-dibromo-3-pentylthieno[3,2-b]thiophene](/data/chemimg/3778200/1472641-54-5.png)
![Stannane, 1,1'-[4,8-bis(dodecyloxy)benzo[1,2-b:4,5-b']dithiophene-2,6-diyl]bis[1,1,1-trimethyl-, polymer with 2,5-dibromo-3-pentylthieno[3,2-b]thiophene](/data/chemimg/3778200/1472641-54-5_b.png)
![2,1,3-Benzothiadiazole, 4,7-bis(5-bromo-6-pentylthieno[3,2-b]thien-2-yl)-5,6-bis(octyloxy)-](/data/chemimg/3777700/1472641-53-4.png)
![2,1,3-Benzothiadiazole, 4,7-bis(5-bromo-6-pentylthieno[3,2-b]thien-2-yl)-5,6-bis(octyloxy)-](/data/chemimg/3777700/1472641-53-4_b.png)
![2,1,3-Benzothiadiazole, 5,6-bis(octyloxy)-4,7-bis(6-pentylthieno[3,2-b]thien-2-yl)-](/data/chemimg/3777700/1472641-52-3.png)
![2,1,3-Benzothiadiazole, 5,6-bis(octyloxy)-4,7-bis(6-pentylthieno[3,2-b]thien-2-yl)-](/data/chemimg/3777700/1472641-52-3_b.png)
![Stannane, 1,1'-[4,8-bis(dodecyloxy)benzo[1,2-b:4,5-b']dithiophene-2,6-diyl]bis[1,1,1-trimethyl-](/data/chemimg/139400/1044795-08-5.png)
![Stannane, 1,1'-[4,8-bis(dodecyloxy)benzo[1,2-b:4,5-b']dithiophene-2,6-diyl]bis[1,1,1-trimethyl-](/data/chemimg/139400/1044795-08-5_b.png)
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![4-[(E)-1H-indazol-6-yldiazenyl]-N,N-dimethylaniline](http://img.cochemist.com/ccimg/17400/17309-87-4.png)
![4-[(E)-1H-indazol-6-yldiazenyl]-N,N-dimethylaniline](http://img.cochemist.com/ccimg/17400/17309-87-4_b.png)
![3'H-Cyclopropa[1,9][5,6]fullerene-C60-Ih-3'-butanoic acid, 3'-phenyl-, [3,4,5-tris(octyloxy)phenyl]methyl ester](/data/chemimg/3719600/1435644-47-5.png)
![3'H-Cyclopropa[1,9][5,6]fullerene-C60-Ih-3'-butanoic acid, 3'-phenyl-, [3,4,5-tris(octyloxy)phenyl]methyl ester](/data/chemimg/3719600/1435644-47-5_b.png)
