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  

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

作　　者：刘慧[1] 陈妍 陈娜 刘诗咏 Hui Liu;Yan Chen;Na Chen;Shi-yong Liu(College of Chemistry and Chemical Engineering,Jiangxi University of Science and Technology,Ganzhou,341000)

机构地区：[1]江西理工大学化学化工学院,赣州341000

出　　处：《高分子学报》2023年第7期1122-1130,共9页Acta Polymerica Sinica

基　　金：国家自然科学基金(基金号22169009)资助项目.

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-n(n=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(VOC),短路电流密度(JSC)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VOC,JSC和FF.本文中所发展的C―H键直接芳基化反应可有效调节π-共轭长度,从而实现高性能非富勒烯受体的高效率筛选.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 ofπ-conjugation lengths(DFPC-2Cl-n(n=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(VOC),short current(JSC),and fill factor(FF).The broadest and highest EQE and suitable BHJ morphology of DFPC-2Cl-2-based OSC enabled the highest JSC and FF among the three UFRAs.The combination of chlorine terminal group with the regulatedπ-conjugation lengths can finely tune the frontier molecular orbital(FMO)levels to obtain new-type oligomeric UFRAs with the elevated VOC,JSC,and FF.The current work demonstrates that direct C-H arylation is a robust and atom-economic strategy to tailor theπ-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 

分 类 号：TM914.4[电气工程—电力电子与电力传动] TQ317[化学工程—高聚物工业]