Confusion Approach Modulated Syntheses of Corrorin Parasitized Hexaphyrins(1.1.1.1.1.0) and the Oxidative Ring Cleavage Behavior

Yue Xu; Bin Zhu; Qizhao Li; Glib Baryshnikov; Mingbo Zhou; Chengjie Li; Feng Sha; Xinyan Wu; Hans Ågren; Jianxin Song; Yongshu Xie

doi:10.1021/acs.orglett.1c03057

Confusion Approach Modulated Syntheses of Corrorin Parasitized Hexaphyrins(1.1.1.1.1.0) and the Oxidative Ring Cleavage Behavior

Org Lett. 2021 Nov 5;23(21):8307-8311. doi: 10.1021/acs.orglett.1c03057. Epub 2021 Oct 11.

Authors

Yue Xu¹, Bin Zhu¹, Qizhao Li^{1

2}, Glib Baryshnikov³, Mingbo Zhou², Chengjie Li¹, Feng Sha¹, Xinyan Wu¹, Hans Ågren⁴, Jianxin Song², Yongshu Xie¹

Affiliations

¹ Key Laboratory for Advanced Materials and Institute of Fine Chemicals, Shanghai Key Laboratory of Functional Materials Chemistry, School of Chemistry & Molecular Engineering, State Key Laboratory of Bioreactor Engineering, Laboratory of Pharmaceutical Crystal Engineering & Technology, School of Pharmacy, East China University of Science & Technology, 200237 Shanghai, China.
² Key Laboratory of the Assembly and Application of Organic Functional Molecules of Hunan Province, Hunan Normal University, 410081 Changsha, China.
³ Department of Science and Technology, Laboratory of Organic Electronics, Linköping University, SE-601 74 Norrköping, Sweden.
⁴ Department of Physics and Astronomy, Uppsala University, SE-751 20 Uppsala, Sweden.

PMID: 34633197
DOI: 10.1021/acs.orglett.1c03057

Abstract

A corrorin parasitized hexaphyrin(1.1.1.1.1.0) 1 was synthesized by [4 + 4] condensation, and subsequent treatment with PbO₂ afforded hexaphyrin 2 appended with a dipyrrinone moiety via regioselective opening of the corrorin ring. In contrast, oxidation of the corresponding corrorin-N-confused hexaphyrin(1.1.1.1.1.0) hybrid 3 afforded only a keto adduct 4. As a result, the planarity and aromaticity of the hexaphyrin moiety can be modulated.