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Issue 6, 2018
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Porphyrinoids as a platform of stable radicals

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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

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Publication details

The article was received on 08 Dec 2017, accepted on 05 Jan 2018 and first published on 08 Jan 2018


Article type: Perspective
DOI: 10.1039/C7SC05210C
Citation: Chem. Sci., 2018,9, 1408-1423
  • Open access: Creative Commons BY-NC license
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    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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