Synthesis and physicochemical characterization of meso-functionalized corroles: Precursors of organic-inorganic hybrid materials

Abstract

Cobalt(III) corroles exhibit an infinite selectivity for the coordination of carbon monoxide towards dioxygen and dinitrogen. This peculiar property thus allows their use as sensing devices for CO detection. Here are described the syntheses and physico-chemical characterization of meso mono-, bis-and tris(triethoxysilyl)-functionalized corroles, precursors of organic-inorganic materials. The corrole ring formation was achieved in every case using the "2+1" method involving the reaction of two equivalents of an encumbered dipyrromethane with one equivalent of an aromatic aldehyde in the presence of a catalytic amount of trifluoroacetic acid. The functionalization of the corrole by triethoxysilyl chains was carried out by a condensation reaction of an isocyanate, bearing a triethoxysilyl termination, either on an amino or hydroxy group. Each final compound and intermediate were characterized by various physico-chemical techniques such as 1H NMR, UV/Vis, MALDI/TOF or EI mass spectrometry and elemental analysis. © Wiley-VCH Verlag GmbH & Co. KGaA, 2005.