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高度区域选择性直接C-H芳基化:用于光电子学的基于对称二噻吩并苯二甲酰亚胺的π共轭分子的简便构建

Highly Regioselective Direct C-H Arylation: Facile Construction of Symmetrical Dithienophthalimide-Based -Conjugated Molecules for Optoelectronics.

作者信息

Li Xiang-Chun, Xue Yibo, Song Wan, Yan Yu, Min Jie, Liu Fang, Liu Xu, Lai Wen-Yong, Huang Wei

机构信息

Key Laboratory for Organic Electronics and Information Displays, Institute of Advanced Materials (IAM), Nanjing University of Posts & Telecommunications, 9 Wenyuan Road, Nanjing 210023, China.

Frontiers Science Center for Flexible Electronics, Xi'an Institute of Flexible Electronics (IFE) and Xi'an Institute of Biomedical Materials & Engineering, Northwestern Polytechnical University, 127 West Youyi Road, Xi'an 710072, China.

出版信息

Research (Wash D C). 2020 Aug 30;2020:9075697. doi: 10.34133/2020/9075697. eCollection 2020.

Abstract

Controllable direct C-H arylation with high regioselectivity is highly desirable yet remains a formidable challenge. Herein, a facile regioselective direct C-H arylation is developed for efficient construction of a variety of symmetrical dithienophthalimide-based -conjugated molecules. The resulting methodology is applicable to a wide range of substrates, from electron-rich units to electron-deficient units with large steric end groups. Aryl halides have been confirmed to be able to couple with dithienophthalimide (DTI) via direct C-H arylation, showing high regioselectivity. Varying the functional end groups onto the DTI core has been demonstrated to fine tune the emission colors to cover most of the visible spectra. The results suggest a facile strategy towards highly selective direct C-H arylation, opening the prospects towards efficient construction of -conjugated molecules for various potential optoelectronic applications.

摘要

具有高区域选择性的可控直接C-H芳基化是非常理想的,但仍然是一个巨大的挑战。在此,开发了一种简便的区域选择性直接C-H芳基化方法,用于高效构建各种基于对称二噻吩并苯二甲酰亚胺的π共轭分子。所得方法适用于广泛的底物,从富电子单元到具有大空间端基的缺电子单元。已证实芳基卤化物能够通过直接C-H芳基化与二噻吩并苯二甲酰亚胺(DTI)偶联,显示出高区域选择性。已证明在DTI核上改变功能端基可微调发射颜色以覆盖大部分可见光谱。结果表明了一种实现高选择性直接C-H芳基化的简便策略,为高效构建用于各种潜在光电子应用的π共轭分子开辟了前景。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fdb7/7510346/96a436923e16/RESEARCH2020-9075697.sch.001.jpg

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