Calixcorrole

Abstract

We recently reported that DDQ-mediated oxidative coupling of pyrrole to a free-base meso-triarylcorrole in dichloromethane at room-temperature results in the near-instantaneous formation of pyrrole-appended isocorroles. Herein we report that the use of refluxing dichloromethane and longer reaction times results in the oxidative addition of a second molecule of pyrrole, affording a novel isoporphyrinoid macrocycle calixcorrole in up to 47% yield.

Transition-Metal Isocorroles as Singlet Oxygen Sensitizers

“…Recently, we reported exceptionally facile “one-minute” synthesis of pyrrole-appended isocorroles. , The present study is aimed at facilitating their applications, especially in the biomedical arena. Key results obtained here include (a) an optimization of the synthesis and isolation of a free-base isocorrole, (b) palladium, platinum, and manganese insertion, (c) photophysical characterization of the resulting complexes, and (d) measurements of the complexes’ ability to sensitize singlet oxygen formation.…”