Meso-5-Bromo-10,15,20-tris(p-tolyl)-21-thiaporphyrin as a precursor for the synthesis of novel compounds

Abstract

The synthesis of eight novel compounds with meso-5-bromo-10,15,20-tri(p-tolyl)-21-thiaporphyrin as a key synthon under mild Pd-coupling conditions is reported. The title compound was prepared easily by treating the readily available 10,15,20-tri(p-tolyl)-21-thiaporphyrin with N-bromosuccinimide at room temperature for 10 min. The use of the title compound was demonstrated by synthesizing 21-thiaporphyrin-based complex systems such as ethyne-bridged N₃S-N₃S dyad, phenylethyne-bridged N₃S-N₃O dyad, N₃S-N₂S₂ dyad, meso-meso-linked ZnN₄-N₃S dyad and ZnN₄-N₃S-ZnN₄ triad under mild Pd-mediated coupling conditions. The steady-state fluorescence studies indicated a possibility of an efficient energy transfer between the two porphyrin subunits in the dyads and triad.