Issue 6, 2018

Porphyrinoids as a platform of stable radicals

Abstract

The non-innocent ligand nature of porphyrins was observed for compound I in enzymatic cycles of cytochrome P450. Such porphyrin radicals were first regarded as reactive intermediates in catabolism, but recent studies have revealed that porphyrinoids, including porphyrins, ring-contracted porphyrins, and ring-expanded porphyrins, display excellent radical-stabilizing abilities to the extent that radicals can be handled like usual closed-shell organic molecules. This review surveys four types of stable porphyrinoid radical and covers their synthetic methods and properties such as excellent redox properties, NIR absorption, and magnetic properties. The radical-stabilizing abilities of porphyrinoids stem from their unique macrocyclic conjugated systems with high electronic and structural flexibilities.

Graphical abstract: Porphyrinoids as a platform of stable radicals

Article information

Article type
Perspective
Submitted
08 Dec. 2017
Accepted
05 Janv. 2018
First published
08 Janv. 2018
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2018,9, 1408-1423

Porphyrinoids as a platform of stable radicals

D. Shimizu and A. Osuka, Chem. Sci., 2018, 9, 1408 DOI: 10.1039/C7SC05210C

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