Electropolymerization on ITO-Coated Glass Slides of a Series of π-Extended BODIPY Dyes with Redox-Active Meso-Substituents

A series of meso-carbazole and meso-pyrene boron dipyrromethene(BDP) dyes have been synthesized using a two-step method. This simplified synthetic method did not require catalysts or oxidizing agents. Solution spectroscopic and electrochemical studies indicate that the HOMO and LUMO energies are dependent on the extent of pi-conjugation associated with the pyrroles. Solution electrochemistry of the dyes in chloroform reveal film formation onto glassy carbon electrodes. Electrolysis of chloroform solutions of the dyes using indium tin oxide (ITO) glass slides as the working electrode show, using UV/vis spectroscopy, the formation of films. For two of the dyes, the BODIPY structure stays in tact upon electrolysis, exhibiting sharp absorption peaks on the ITO slides similar to that observed for the same dyes in solution.