Synthesis of 2,2′-biphenyl-fused porphyrins: installation of directly fused seven-membered ring

Author:

Fan Shuibo1,Tan Zhiqiang1,Liang Min1,Zhou Mingbo1,Rao Yutao1,Xu Ling1,Osuka Atsuhiro1,Song Jianxin1

Affiliation:

1. College of Chemistry and Chemical Engineering, Key Laboratory of Chemical Biology and Traditional Chinese, Medicine Research (Ministry of Education of China), Key Laboratory of the Assembly and Application of Organic Functional Molecules of Hunan Province, Hunan Normal University, Changsha 410081, China

Abstract

2,2[Formula: see text]-Biphenyl-fused Ni(II) porphyrins were synthesized by two methods. One was oxidative fusion reaction of meso-(biphen-2-yl)-substituted Ni(II) porphyrin with the combination of 2,3-dichloro-5,6-dicyano-[Formula: see text]-benzoquinone (DDQ) and Sc(OTf)3 and the other was Pd-catalyzed intramolecular cyclization of meso-(2[Formula: see text]-chlorobiphen-2-yl)-substituted Ni(II) porphyrin. These fused products showed contorted structures owing to the installed seven-membered carbocycle(s) that were revealed by X-ray crystallographic analysis and exhibited moderately red-shifted absorption bands.

Funder

National Natural Science Foundation of China

Scientific Research Fund of Hunan Provincial Science and Technology Department

Scientific Research Fund of Changsha Science and Technology Bureau

Scientific Research Fund of Hunan Provincial Education Department

Science and Technology Planning Project of Hunan Province

Science and Technology Innovation Program of Hunan Province

Publisher

World Scientific Pub Co Pte Ltd

Subject

General Chemistry

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