Electrochemical and spectral properties of meta-linked 1,3,5-tris(aryl)benzenes and 2,4,6-tris(aryl)-1-phenoles, and their polymers

We present electrochemical and spectral properties of symmetric monomers 1,3,5-tris(aryl)benzenes and 2,4,6-tris(aryl)-1-phenols and their polymers. These compounds contain thienyl, furyl or EDOT moieties attached to central benzene or phenol ring at the meta-position, synthesized by a Stille cross-coupling procedure. All monomers are electroactive and undergo electropolymerization creating thin films on an electrode surface. Polymers with meta-linkages were obtained by electrochemical oxidation. Detailed cyclic voltammetry and in situ UV–vis spectroelectrochemistry show that polymers with hydroxy groups exhibit higher conductivity and better stability than with benzene core. Interesting and different behavior occurs for 2,4,6-tris(2-thienyl)-1-phenol, for which the characteristic, sharp, redox peak is observed.