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Issue 19, 2008
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Subporphyrins: emerging contracted porphyrins with aromatic 14π-electronic systems and bowl-shaped structures: rational and unexpected synthetic routes

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Abstract

Subporphyrin is a ring-contracted porphyrin congener consisting of three pyrrolic subunits domed in a C3 symmetric bowl arrangement. Subporphyrin had long been elusive until the first synthesis of tribenzosubporphine in 2006. Shortly after, synthetic protocols of subpyriporphyrin, meso-aryl-substituted subporphyrins, and meso-aryl substituted subchlorins were developed. Subporphyrins display interesting properties including distinct aromaticity arising from 14π-electronic conjugation, green fluorescence, and strong influences of meso-aryl substituents on the electronic network of the macrocycle. Besides the rational synthetic routes, an unexpected route to a specific subporphyrin from a [32]heptaphyrin(1.1.1.1.1.1.1) was discovered via a thermal extrusion reaction upon Cu(II)–B(III) cooperative metallation. In this Perspective, we review recent progress on subporphyrin chemistry and unprecedented ring-splitting reactions of medium size expanded porphyrins that are triggered upon metallation.

Graphical abstract: Subporphyrins: emerging contracted porphyrins with aromatic 14π-electronic systems and bowl-shaped structures: rational and unexpected synthetic routes

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Publication details

The article was received on 02 Jan 2008, accepted on 05 Feb 2008 and first published on 04 Mar 2008


Article type: Perspective
DOI: 10.1039/B719808F
Citation: Dalton Trans., 2008,0, 2517-2526
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    Subporphyrins: emerging contracted porphyrins with aromatic 14π-electronic systems and bowl-shaped structures: rational and unexpected synthetic routes

    Y. Inokuma and A. Osuka, Dalton Trans., 2008, 0, 2517
    DOI: 10.1039/B719808F

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