125607-30-9Relevant articles and documents
Alternating copolymers based on 2,1,3-benzothiadiazole and hexylthiophene: Positioning effect of hexyl chains on the photophysical and electrochemical properties
El-Shehawy, Ashraf A.,Abdo, Nabiha I.,El-Barbary, Ahmed A.,Lee, Jae-Suk
, p. 4841 - 4852 (2011)
A series of donor-acceptor alternating π-conjugated copolymers based on 2,1,3-benzothiadiazole and hexylthiophene units has been synthesized by the palladium-catalyzed Stille cross-coupling method. Various precursory monomers possessing dibromo and bis(tributylstannyl) functionalities were readily prepared in high yields. Microwave-assisted polymerization proved efficient for the production of high-molecular-weight copolymers, ranging from 13550 to 52490 g mol-1. All copolymers exhibited excellent solubilities in most common organic solvents. The thermal properties of these copolymers were investigated by thermogravimetric analysis and differential scanning calorimetry, and the polymers showed high thermal stabilities. Incorporation of the benzothiadiazole unit into polyhexylthiophene chains affected the photophysical and electrochemical properties. The thin-film absorption spectra of all polymers are significantly red-shifted relative to the corresponding absorption bands in solution and exhibit broader absorption bands. The optical band gaps were estimated to be in the range of 2.02-1.74 eV. The highest occupied and lowest unoccupied molecular orbital energy levels are in the ranges of -5.37 to -5.66 eV and -3.33 to -3.44 eV, respectively. In the X-ray diffraction analysis of the deposited film of the copolymer P3, strong diffraction peaks were observed at 2θ = 5.72° (15.43 A) and 23.12° (3.84 A). These values relate to the distances between chains with interdigitated hexyl chains and to π-π stacking between the conjugated chains.
Simple non-fullerene electron acceptors with unfused core for organic solar cells
Li, Yao,Xu, Yunhua,Yang, Fan,Jiang, Xudong,Li, Cheng,You, Shengyong,Li, Weiwei
, p. 222 - 224 (2019)
Two simple electron acceptors based on unfused bithiophene core and 1,1-dicyanomethylene-3-indanone end group were easily prepared via three synthetic steps. These acceptors exhibited broad absorption in the range of 300 nm to 800 nm, aligned energy levels and high crystallinity. When combined with a wide band gap donor polymer in non-fullerene solar cells, an initial power conversion efficiency of 2.4% was achieved. The relatively low efficiencies were due to the large phase separation in blended thin films, which is originated from their high aggregation tendency in thin films. Our results suggest that these electron acceptors with unfused core are promising candidates for commercial application of solar cells due to the low cost starting materials and facile synthesis.
The synthesis of head-to-tail (H-T) dimers of 3-substituted thiophenes by the hypervalent iodine(III)-induced oxidative biaryl coupling reaction
Dohi, Toshifumi,Morimoto, Koji,Kiyono, Yorito,Maruyama, Akinobu,Tohma, Hirofumi,Kita, Yasuyuki
, p. 2930 - 2932 (2005)
The head-to-tail (H-T) dimers could be obtained selectively by the oxidative coupling reaction of 3-substituted thiophenes using a combination of hypervalent iodine(III) reagents and trimethylsilyl trifluoromethanesulfonate. The Roval Society of Chemistry 2005.
Intramolecular Noncovalent Interaction-Enabled Dopant-Free Hole-Transporting Materials for High-Performance Inverted Perovskite Solar Cells
Cao, Yan,Chen, Zhicai,Gao, Peng,Guo, Xugang,Huang, Jun,Lai, Ziwei,Liao, Qiaogan,Su, Mengyao,Wang, Dong,Woo, Han Young,Wu, Ziang,Yang, Kun,Zhang, Zilong
, (2021/12/06)
Intramolecular noncovalent interactions (INIs) have served as a powerful strategy for accessing organic semiconductors with enhanced charge transport properties. Herein, we apply the INI strategy for developing dopant-free hole-transporting materials (HTMs) by constructing two small-molecular HTMs featuring an INI-integrated backbone for high-performance perovskite solar cells (PVSCs). Upon incorporating noncovalent S???O interaction into their simple-structured backbones, the resulting HTMs, BTORA and BTORCNA, showed self-planarized backbones, tuned energy levels, enhanced thermal properties, appropriate film morphology, and effective defect passivation. More importantly, the high film crystallinity enables the materials with substantial hole mobilities, thus rendering them as promising dopant-free HTMs. Consequently, the BTORCNA-based inverted PVSCs delivered a power conversion efficiency of 21.10 % with encouraging long-term device stability, outperforming the devices based on BTRA without S???O interaction (18.40 %). This work offers a practical approach to designing charge transporting layers with high intrinsic mobilities for high-performance PVSCs.
Convenient synthesis of organic-electronics-oriented building blocks via on-water and under-air homocoupling of (hetero)aryl iodides
Chen, Yi-An,Liu, Ching-Yuan
, p. 74180 - 74188 (2015/09/21)
We report herein an operationally simple homocoupling reaction that targets the convenient synthesis of organic-electronically important building blocks. A variety of synthetically useful bithiophene derivatives and functionalized biphenyls are efficiently prepared by an on-water and under-air protocol using Pd/C as catalyst. We find that Pd/C gives generally higher and cleaner homocoupling conversions than using Pd(OAc)2 in the cases of (hetero)aryl iodides since Pd(OAc)2 triggers more side reactions including dehalogenations and oligomerizations. Under the optimum conditions, a broad range of functional groups such as ester, ketone, aldehyde, nitrile, nitro, chloride, and bromide are well tolerated. We expect the present methodology would make a valuable synthetic contribution towards bridging green chemistry with thiophene-based organic materials.
