Substituent effects in the electropolymerization of aromatic heterocyclic compounds

The electrooxidation of indole, substituted indoles, and thianaphthene yield semiconducting polymers with conductivities of 10-2 ohm-1 cm-1. Substituents determine whether electropolymerization occurs or whether soluble products are formed. The relative importance of these pathways is dependent on the stability of the intermediate radical cation. The electronic effects induced by substituents are investigated by INDO molecular orbital calculations. © 1984 American Chemical Society.