Stepwise Extended π-Conjugation Lengths of Chlorinated Oligomeric Non-fullerene Acceptors Accessed<italic style="font-style: italic"> via</italic> Direct C―H Arylation

Hui Liu; Yan Chen; Na Chen; Shi-yong Liu

doi:10.11777/j.issn1000-3304.2022.22398

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Stepwise Extended π-Conjugation Lengths of Chlorinated Oligomeric Non-fullerene Acceptors Accessed via Direct C―H Arylation

Research Article | 更新时间：2023-06-21

- Stepwise Extended π-Conjugation Lengths of Chlorinated Oligomeric Non-fullerene Acceptors Accessed via Direct C―H Arylation
  增强出版
- ACTA POLYMERICA SINICA Vol. 54, Issue 7, Pages: 1122-1130(2023)
- 作者机构：
  
  江西理工大学化学化工学院赣州 341000
- 作者简介：
  
  Shi-yong Liu, E-mail: chelsy@jxust.edu.cn
- 基金信息：
- DOI：10.11777/j.issn1000-3304.2022.22398
  CLC：
- Published：20 July 2023，
  
  Published Online：22 February 2023，
  
  Received：21 November 2022，
  
  Accepted：27 December 2022
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刘慧,陈妍,陈娜等.C―H键直接芳基化合成共轭长度连续递增的氯代低聚物非富勒烯受体[J].高分子学报,2023,54(07):1122-1130.

Liu Hui,Chen Yan,Chen Na,et al.Stepwise Extended π-Conjugation Lengths of Chlorinated Oligomeric Non-fullerene Acceptors Accessed via Direct C―H Arylation[J].ACTA POLYMERICA SINICA,2023,54(07):1122-1130.
刘慧,陈妍,陈娜等.C―H键直接芳基化合成共轭长度连续递增的氯代低聚物非富勒烯受体[J].高分子学报,2023,54(07):1122-1130. DOI： 10.11777/j.issn1000-3304.2022.22398.

Liu Hui,Chen Yan,Chen Na,et al.Stepwise Extended π-Conjugation Lengths of Chlorinated Oligomeric Non-fullerene Acceptors Accessed via Direct C―H Arylation[J].ACTA POLYMERICA SINICA,2023,54(07):1122-1130. DOI： 10.11777/j.issn1000-3304.2022.22398.

摘要

受体材料的低成本合成对于有机光电器件的实用化具有重要意义. 通过原子及步骤经济的C―H键直接芳基化反应(DACH)合成了一系列A-D-A型共轭长度逐步递增的氯取代的低聚物非稠合电子受体(DFPC-2Cl-

(

= 1~3))，系统研究了光电化学性质和器件性能与共轭长度之间的构-效关系. 同时，在端基引入氯原子，可有效降低最高分子占有轨道(HOMO)能级. 研究发现，DFPC-2Cl-2表现出最高的PCE (7.55%)，主要归因于开路电压(

)，短路电流密度(

)和填充因子(FF)的改善，表明氯化端基作为一种低成本方法，可有效调节光电性质并同时增强

，

和FF. 本文中所发展的C―H键直接芳基化反应可有效调节

-共轭长度，从而实现高性能非富勒烯受体的高效率筛选.

Abstract

Low-cost and efficient synthesis of acceptors plays a key role in the commercialization of organic optoelectronic devices. So far

the unfused-ring acceptors (UFRAs) with chlorine terminal groups has rarely been reported in the past years. In this work

a series of A-D-A type chlorinated oligomeric UFRAs with the stepwise extension of

-conjugation lengths (DFPC-2Cl-

(

= 1‒3)) are designed and successfully synthesized

via

direct C―H arylation. The conjugation length dependence of optoelectronic properties and photovoltaic performances have been systematically investigated

revealing that DFPC-2Cl-2 achieves the highest power conversion efficiency (7.55%) due to the significantly enhanced open voltage (

)

short current (

)

and fill factor (FF). The broadest and highest EQE and suitable BHJ morphology of DFPC-2Cl-2-based OSC enabled the highest

and FF among the three UFRAs. The combination of chlorine terminal group with the regulated

-conjugation lengths can finely tune the frontier molecular orbital (FMO) levels to obtain new-type oligomeric UFRAs with the elevated

and FF. The current work demonstrates that direct C―H arylation is a robust and atom-economic strategy to tailor the

-conjugation lengths of UFRAs

which will provide a guidance for the design

synthesis and screening of high-performance non-fullerene acceptors for organic solar cell applications.

关键词

有机太阳能电池低聚物非稠合电子受体氯取代原子及步骤经济C―H键直接芳基化

Keywords

Organic solar cellOligomeric unfused electron acceptorsChloric substituentAtom- and step-economyC―H direct arylation

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⁰

Stepwise Extended π-Conjugation Lengths of Chlorinated Oligomeric Non-fullerene Acceptors Accessed via Direct C―H Arylation

DOI：10.11777/j.issn1000-3304.2022.22398

摘要

Abstract

关键词

Keywords

references