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Review | Regular issue | Vol 100, No. 8, 2020, pp.1123-1162
Published online, 9th April, 2020
DOI: 10.3987/REV-20-927
5,15-Diheteroporphyrins Synthesized from α,α'-Dihalodipyrrin as a Key Building Block

Soji Shimizu*

*Department of Chemistry and Biochemistry, Graduate School of Engineering, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka 819-0395, Japan

Abstract

A facile synthesis of meso-aryl-substituted α,α'-dihalodipyrrins and their use as starting materials in the porphyrin synthesis have enabled creation of various porphyrin analogues containing heteroatoms at two opposite meso-positions, namely 5,15-positions. Incorporation of lone pair electrons into the 18π-electron aromatic conjugated system of porphyrin allows the system to attain antiaromaticity with unique optical and electrochemical properties. This review summarizes the recent development in the chemistry of 5,15-diheteroporphyrins synthesized from meso-aryl-substituted α,α'-dihalodipyrrins.