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,Journal of Materials Chemistry C

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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
Journal of Materials Chemistry C ( IF 5.7 ) Pub Date : 2020-12-31 , DOI: 10.1039/d0tc05261b
Gao-Yang Ge _{1,

2,

3,

4,

5} , Wentao Xiong _{6,

7,

8,

9} , Kai-Kai Liu _{1,

2,

3,

4,

5} , Hwa Sook Ryu _{10,

11,

12,

13} , Shi-Sheng Wan _{1,

2,

3,

4,

5} , Bo Liu _{9,

14,

15,

16,

17} , Asif Mahmood _{1,

2,

3,

4,

5} , Hai-Rui Bai _{1,

2,

3,

4,

5} , Jun-Fang Wang _{1,

2,

3,

4,

5} , Zhaohui Wang _{9,

14,

15,

16,

17} , Han Young Woo _{10,

11,

12,

13} , Yanming Sun _{6,

7,

8,

9} , Jin-Liang Wang _{1,

2,

3,

4,

5}

Affiliation

Key Laboratory of Cluster Science of Ministry of Education
Beijing Key Laboratory of Photoelectronic/Electrophotonic Conversion Materials
School of Chemistry and Chemical Engineering
Beijing Institute of Technology
Beijing
School of Chemistry
Beihang University
Beijing 100191
China
Department of Chemistry
Korea University
Seoul 136-713
Republic of Korea
Beijing National Laboratory for Molecular Sciences
Institute of Chemistry
Chinese Academy of Sciences
Beijing 100190

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- or para-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.

中文翻译：

含硒烯的中心核和区域异构的单氯化末端对硒基非富勒烯受体的分子堆积，结晶度，薄膜形态和光电性能的协同作用

我们合成了一对不含区域异构体的亚硒基非富勒烯受体（NFAs）（TSeIC-M-Cl和TSeIC-P-Cl），它们具有相同的indacenodithieno [3,2- b ]硒烯核和两种类型的在不同位置带有氯取代基的单氯化（2,3-二氢-3-氧代1 H-茚-1-基）丙腈（INCN）端基（间位或对位相对于二氰基亚乙烯基部分的-位置。与TSeIC-M-Cl相比，由于IC-P-Cl的弱吸电子能力，TSeIC-P-Cl的吸收光谱略有蓝移，分子能级升高。此外，由于单晶中Cl⋯H / C和Se⋯π分子之间存在大量且强烈的相互作用，TSeIC-P-Cl具有三维分子堆积，具有矩形互穿网络和较高的π轨道度电荷传输的重叠，导致TSeIC-P-Cl膜中的电子迁移率高于具有线性堆叠结构的TSeIC-M-Cl。此外，PBT1-C：TSeIC-P-Cl共混膜表现出更好的混溶性，并形成具有合适的相分离和优先的面朝取向的纳米原纤维状网络。最后，PBT1-C：TSeIC-P-Cl器件的效率为11.26％，远胜过PBT1-C：TSeIC-M-Cl器件（9.72％）。这项工作强调，将中心芯末端的硒烯环融合并调整INCN上氯原子的位置是多重调节分子堆积，结晶度和膜形态的替代方法，从而实现了无区域异构体的单卤代INCN的NFA。

更新日期：2021-01-20

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