Copper-promoted domino cyanation/Ullmann coupling toward difunctionalized acenaphthylenes with various optoelectronic properties  

作　　者：Yang Wang Yang Hu Junfeng Guo Zongrui Wang Yang Li Fengxiang Qie Chunfeng Shi Lei Zhang Yonggang Zhen 

机构地区：[1]Advanced Innovation Center for Soft Matter Science and Engineering,State Key Laboratory of Organic-Inorganic Composites,Beijing University of Chemical Technology,Beijing 100029,China [2]Wuhan National Laboratory for Optoelectronics,Huazhong University of Science and Technology,Wuhan 430074,China [3]State Key Laboratory of Luminescent Materials and Devices,South China University of Technology,Guangzhou 510640,China [4]Normal College,Shenyang University,Shenyang 110044,China [5]State Key Laboratory of Catalytic Materials and Reaction Engineering,Research Institute of Petroleum Processing,SINOPEC,Beijing 100083,China

出　　处：《Science China Chemistry》2023年第5期1450-1456,共7页中国科学（化学英文版）

基　　金：supported by the Fundamental Research Funds for the Central Universities(buctrc202103,buctrc202128);the National Natural Science Foundation of China(21975263,22171019,52103200);SINOPEC(222131);the Open Project Program of Wuhan National Laboratory for Optoelectronics(2021WNLOKF005);the State Key Laboratory of Fine Chemicals(KF2201,Dalian University of Technology);the State Key Laboratory of Luminescent Materials and Devices(2022skllmd-14);the State Key Laboratory of Supramolecular Structure and Materials(SKLSSM2022036)。

摘　　要：Tremendous progress has been made on aromatic fusion of acenaphthylene towards organic semiconductors.However,scarce studies focus on the functionalization of acenaphthylene without resort to aromatic extension,although vinylene double bond is highly reactive ascribed to the ring strain of the fused cyclopentene.Herein,for the first time we employ copper-promoted domino cyanation/Ullmann coupling to achieve a series of difunctionalized acenaphthylene imides(ANIs)with varied optoelectronic properties.Both Ullmann homocoupling and crosscoupling can be combined with cyanation for difunctionalization of ANIs.The introduction of cyano groups influences oppositely not only the energy levels but also the antiaromaticity of the fivemembered rings in ANIs relative to the dimethylamino substituent due to the electron donating or withdrawing effects.By altering the functional units,the optical and electrical characteristics have been tailored rationally;thus p,n or ambipolar semiconducting properties can be achieved for the ANI derivatives.This article opens up possibilities to the development of organic semiconducting materials based on ANIs without aromatic extension,which is promising for applications in organic electronics.

关 键 词：ACENAPHTHYLENE difunctionalization organic semiconductors organic field-effect transistors 

分 类 号：O621.25[理学—有机化学]