Efficient Construction of Highly-fused Diperylene Bismides by Cu/Oxalic Diamide-promoted Zipper-mode Double C—H Activation

doi:10.1007/s40242-020-9051-3

Chemical Research in Chinese Universities ›› 2020, Vol. 36 ›› Issue (1): 110-114.doi: 10.1007/s40242-020-9051-3

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Efficient Construction of Highly-fused Diperylene Bismides by Cu/Oxalic Diamide-promoted Zipper-mode Double C—H Activation

LU Xiuqiang^1,2, LIN Hui¹, ZHEN Yonggang², DONG Huanli², ZHANG Xiaotao³, HU Wenping³

1. School of Ocean Science and Biochemistry Engineering, Fuqing Branch of Fujian Normal University, Fuzhou 350300, P. R. China;
2. Beijing National Laboratory for Molecular Sciences, Key Laboratory of Organic Solids, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. China;
3. Tianjin Key Laboratory of Molecular Optoelectronic Sciences, Department of Chemistry, School of Sciences, Tianjin University, Tianjin 300072, P. R. China

Received:2019-11-19 Revised:2019-12-19 Online:2020-02-01 Published:2019-12-27
Contact: ZHEN Yonggang, DONG Huanli, HU Wenping E-mail:zhenyg@iccas.ac.cn;dhl522@iccas.ac.cn;huwp@tju.edu.cn
Supported by:
Supported by the National Natural Science Foundation of China(Nos.51503037, 51822308, 51733004, 21661132006), the Program for New Century Excellent Talents in Fujian Province Universities, China, the Fund of the Youth Innovation Promotion Association of the Chinese Academy of Sciences and the Education and Scientific Research Project for Young and Middle-aged Teachers in Fujian Province, China (No.JT180633).

Abstract

Abstract: Copper/oxalic diamide-promoted dimerization of tetrachlorinated perylene bisimide to construct highly-fused diperylene bisimides through Ullmann coupling and zipper-mode double C—H activation has been developed in this study. This one-step reaction combining homocoupling with C—H activation proceeded smoothly under the action of inexpensive metal-ligand system. This protocol is expected to expand the available synthetic tools for condensed ring systems of perylene bisimide(PBIs).

Key words: Organic semiconductor, Perylene bisimide, Dimerization, Ullmann homocoupling, C—H activation

LU Xiuqiang, LIN Hui, ZHEN Yonggang, DONG Huanli, ZHANG Xiaotao, HU Wenping. Efficient Construction of Highly-fused Diperylene Bismides by Cu/Oxalic Diamide-promoted Zipper-mode Double C—H Activation[J]. Chemical Research in Chinese Universities, 2020, 36(1): 110-114.

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Efficient Construction of Highly-fused Diperylene Bismides by Cu/Oxalic Diamide-promoted Zipper-mode Double C—H Activation

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