Journal
DALTON TRANSACTIONS
Volume -, Issue 19, Pages 2517-2526Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/b719808f
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Subporphyrin is a ring-contracted porphyrin congener consisting of three pyrrolic subunits domed in a C-3 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 14 pi-electronic conjugation, green fluorescence, and strong in fluences 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.
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