Syntheses of bioinspired trisporphyrin scaffoldings from stepwise Suzuki coupling strategies

Abstract

This review presents the synthetic approach for the design of tris(macrocycles) as bio-inspired models for light harvesting devices in plants and photosynthetic bacteria based on cofacial bisporphyrins and a porphyrin unit attached as a side arm. Two types of tris(porphyrins) are described herein depending on the nature of the chromophores of the cofacial bis(porphyrins). The synthetic methodology of a series of trimeric models relies on the versatility of the porphyrin ring acting as a building block, and on successive Suzuki coupling reactions. Various pathways to access such models are presented as the selective and stepwise substitution processes involving different borylated porphyrin synthons can provide either meso-meso-linked linear intermediates or cofacial homo- or hetero-bismacrocycle units. This efficient methodology also allows for the flexibility and fine tuning since different bridges and spacers can be used in the designed trimers. © ISUCT Publishing.