@article{01cc764592ba4cff92d47a33b6de502c,
title = "Synergistic effect of the selenophene-containing central core and the regioisomeric monochlorinated terminals on the molecular packing, crystallinity, film morphology, and photovoltaic performance of selenophene-based nonfullerene acceptors",
abstract = "We synthesize a pair of regioisomer-free selenophene-containing non-fullerene acceptors (NFAs) (TSeIC-M-Cl and TSeIC-P-Cl), which have an identical indacenodithieno[3,2-b]selenophene core and two types of monochlorinated (2,3-dihydro-3-oxo-1H-inden-1-ylidene)propanedinitrile (INCN) end groups with chlorine substituents at different positions (meta- orpara-position relative to the dicyanovinylene moiety), respectively. Compared with TSeIC-M-Cl, TSeIC-P-Cl shows slightly blue-shifted absorption spectra and elevated molecular energy levels owing to the weak electron-withdrawing ability of IC-P-Cl. Besides, owing to the multiple and strong intermolecular Cl⋯H/C and Se⋯π interactions in the single crystal, TSeIC-P-Cl displays three-dimensional molecular packing with a rectangle-like interpenetrating network and a higher degree of π-orbital overlap for charge transport, which results in a higher electron mobility in the film of TSeIC-P-Cl than TSeIC-M-Cl with a linear stacked structure. Moreover, the PBT1-C:TSeIC-P-Cl blend film shows better miscibility and forms a nanofibril-like network with suitable phase separation and a preferential face-on orientation. Finally, the PBT1-C:TSeIC-P-Cl devices yield 11.26% efficiency, which far outperforms the PBT1-C:TSeIC-M-Cl devices (9.72%). This work highlights that the combination of fusing the selenophene ring on the end of the central core and adjusting the position of the chlorine atom on INCN is an alternative way to multiply modulate the molecular packing, crystallinity and film morphology for efficient regioisomer-free monohalogenated INCN-based NFAs.",
author = "Ge, {Gao Yang} and Wentao Xiong and Liu, {Kai Kai} and Ryu, {Hwa Sook} and Wan, {Shi Sheng} and Bo Liu and Asif Mahmood and Bai, {Hai Rui} and Wang, {Jun Fang} and Zhaohui Wang and Woo, {Han Young} and Yanming Sun and Wang, {Jin Liang}",
note = "Funding Information: This work was financially supported by grants from the National Natural Science Foundation of China (No. 21672023, 21971014, and 21472012) and the National Key Research and Development Program of China (2018YFA0901800). Jin-Liang Wang was supported by the Thousand Youth Talents Plan of China and the BIT Teli Young Fellow Recruitment Program. G.-Y. Ge thanks Dr Kai-Kai Liu (Beijing Institute of Technology) for help with the synthesis of TSeIC-P-Cl and the AFM measurement. G.-Y. Ge thanks Han-Jian Zhang, Chao Zhang and Kai-Kai Liu (Beijing Institute of Technology) for the synthesis of IDTSe-2CHO and precursors. G.-Y. Ge thanks Dr Asif Mahmood and Rui Zhu (Beijing Institute of Technology) for density functional theory (DFT) calculations. G.-Y. Ge thanks Dr Shi-Sheng Wan, Hai-Rui Bai, Zhao Jiang, Can Yang, and Hong-Fu Zhi (Beijing Institute of Technology) for fruitful modification of this manuscript. G.-Y. Ge thanks Prof. Qiaoshi An (Beijing Institute of Technology) for fruitful discussion. The authors are grateful to Hwa Sook Ryu and Prof. Han Young Woo (Korea University) for 2D GIWAXS experiments and analysis. The authors thank the Analysis & Testing Center, Beijing Institute of Technology, for NMR and TGA experiments. The authors thank Dr Bo Liu (Chinese Academy of Sciences), Prof. Zhaohui Wang (Chinese Academy of Sciences), Prof. Jian Pei (Peking University), Ze-Fan Yao (Peking University), Yang Lu (Peking University), and Fei-Peng Yuan (Beijing Institute of Technology) for crystallographic measurements and analysis. The authors thank Prof. Jian Pei, Prof. Jie-Yu Wang, and Dr Miao Xiong (Peking University) for help with AFM measurements. The authors acknowledge the research fund for international young scientist from the National Natural Science Foundation of China (No. 21950410533). Funding Information: This work was financially supported by grants from the National Natural Science Foundation of China (No. 21672023, 21971014, and 21472012) and the National Key Research and Development Program of China (2018YFA0901800). Jin-Liang Wang was supported by the Thousand Youth Talents Plan of China and the BIT Teli Young Fellow Recruitment Program. G.-Y. Ge thanks Dr Kai-Kai Liu (Beijing Institute of Technology) for help with the synthesis of TSeIC-P-Cl and the AFM measurement. G.-Y. Ge thanks Han-Jian Zhang, Chao Zhang and Kai-Kai Liu (Beijing Institute of Technology) for the synthesis of IDTSe-2CHO and precursors. G.-Y. Ge thanks Dr Asif Mahmood and Rui Zhu (Beijing Institute of Technology) for density functional theory (DFT) calculations. G.-Y. Ge thanks Dr Shi-Sheng Wan, Hai-Rui Bai, Zhao Jiang, Can Yang, and Hong-Fu Zhi (Beijing Institute of Technology) for fruitful modification of this manuscript. G.-Y. Ge thanks?Prof. Qiaoshi An (Beijing Institute of Technology) for fruitful discussion. The authors are grateful to Hwa Sook Ryu and Prof. Han Young Woo (Korea University) for 2D GIWAXS experiments and analysis. The authors thank the Analysis & Testing Center, Beijing Institute of Technology, for NMR and TGA experiments. The authors thank Dr Bo Liu (Chinese Academy of Sciences), Prof. Zhaohui Wang (Chinese Academy of Sciences), Prof. Jian Pei (Peking University), Ze-Fan Yao (Peking University), Yang Lu (Peking University), and Fei-Peng Yuan (Beijing Institute of Technology) for crystallographic measurements and analysis. The authors thank Prof. Jian Pei, Prof.?Jie-Yu Wang, and Dr Miao Xiong (Peking University) for help with AFM measurements. The authors acknowledge the research fund for international young scientist from the National Natural Science Foundation of China (No. 21950410533). Publisher Copyright: {\textcopyright} The Royal Society of Chemistry 2021.",
year = "2021",
month = feb,
day = "14",
doi = "10.1039/d0tc05261b",
language = "English",
volume = "9",
pages = "1923--1935",
journal = "Journal of Materials Chemistry C",
issn = "2050-7526",
publisher = "Royal Society of Chemistry",
number = "6",
}
