Mechanistic study of the oxidation of 2-amino-3-cyano-4-naphtylthiophene by cyclic voltammetry and UV–Vis–NIR absorption spectroscopy

The anodic oxidation of 2-amino-3-cyano-4-naphtylthiophene (ACNT) was studied for the first time by cyclic voltammetry, digital simulation and in situ spectroelectrochemical techniques. The kinetic data were estimated using the results of fitting the digitally simulated voltammograms to the experimental data. All electrochemical evidence indicates that the oligomerization mechanism is ECE and the main reaction path of the oligomer formation involves the coupling of the dimeric cation radical of RC–PM with neutral ACNT molecules or other radical species. The in situ UV–Vis–NIR spectra of the dimers and oligomeric mixture indicated that new species with a low energy absorption (365, 537, 828, and 1055 nm) formed during the electrooxidaton of ACNT.