Supporting porphyrins on resin-beads by cyanuric chloride linker

Abstract

A straightforward procedure for supporting porphyrin-derivatives onto resin beads has been developed by reacting the commercially available 4,6-dichloro-1,3,5-triazene polymer-bound, with 5-(4-aminophenyl)-10,15,20-triphenylporphyrins as free base and as Zn (II) and Co (II) complexes. The supported porphyrins have been characterized by on-resin UV-vis spectroscopy. Kinetic and Hammett LFER studies have shown that the S N Ar reaction with the triazine-bound reagent occurs at a similar rate for free and metalated complexes, with a nucleophilic strength comparable to that of the unsubstituted aniline (σ p + = 0.07-0.08).