A Comparative Study of Two Different Media Effect on the Electropolymerization of 2-(9-ethylcarbazol-3-yliminomethyl)phenol by Cyclic Voltammetry, Impedance Spectroscopy, XPS, UV-visible Measurements and DFT Calculation

A carbazole-based monomer, 2-(9-ethylcarbazol-3-yliminomethyl)phenol (SIC), was first synthesized and characterized. It was afterward polymerized by potentiostatic methods. Oxidative polymerization of SIC was carried out in two media. The first one (i.e. Bu4NBF4 (0.1M)/MeCN) gives the poly(2-(9-ethylcarbazol-3-yliminomethyl)phenol). However, the second one (LiClO4/MeCN + 35mM HClO4), leads to another polymer, the poly(2-(9-ethylcarbazol-3-yliminomethyl)cyclohexa-2,5-diene-1,4-dione).These two novel polymers will be abbreviated here after as PSIC and PDIC, respectively. If the formation of PSIC was expected, the formation of PDIC in acidic medium isn’t. It was explained by a hydroxyl function oxidation of SIC. The obtained polymers were then characterized by cyclic voltammetry, electrochemical impedance spectroscopy, XPS, IR and UV-Vis spectroscopies. Furthermore, the corresponding electrochemical and optical bandgap values were calculated in order to get an idea about the conductive properties. The related results show that PDIC and PSIC are good conductive polymers.