Stepwise syntheses of core-modified, meso-substituted porphyrins

Abstract

Simple conditions are discovered to afford modified tripyrrin derivatives by condensation of 2,5-bis(α-hydroxymethyl)pyrrole, thiophene and furan derivatives with pyrrole in the presence of acid catalyst. The core-modified porphyrins were synthesized by acid catalyzed 3 + 1 condensation of modified tripyrrins with 2,5-bis(α-hydroxymethyl)-substituted pyrrole, thiophene or furan. This new process gives a single porphyrin isomer and overcome the synthetic problems associated with separation and purification of regioisomeric mixtures.