The electrochemical behavior of two new chalcones, containing carbazole cycle andN,N-disubstituted amino group as terminal electron-donating moieties, was studied. In order to determine a detailed mechanism of their electrochemical oxidation and reduction, comparative analysis of cyclic voltammograms of the chalcones and starting compounds was carried out. It was proven that replacing theN,N-dimethylamino group in the structure of a chalcone with a diphenylamino group significantly changes not only the basic electrochemical characteristics (reduces the HOMO energy value and increases the LUMO energy and the band gap values), but also generally affects the polymerization process. It was also proven that the chalcone containing both a carbazole fragment and a diphenylamino group in its structure is capable of forming oligomeric structures under electrochemical oxidation conditions, due to the sequential dimerization of both electron-donating fragments. Graphic abstract