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, Xin‐Yan Wu, Hans Ågren, Jianxin Song, Yongshu Xie
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.
Topics & Concepts
ChemistryMoietyRegioselectivityRing (chemistry)AdductCleavage (geology)StereochemistryPlanarity testingOxidative cleavageOrganic chemistryCrystallographyCatalysisGeotechnical engineeringFracture (geology)EngineeringPorphyrin and Phthalocyanine ChemistryPhotosynthetic Processes and MechanismsLuminescence and Fluorescent Materials