meso-5-bromo-10,15,20-tiri(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. (C) Wiley-VCH Verlag GmbH & Co.