Electrochemical, EPR, and computational study of pyrene conjugates—precursors for novel type of organic semiconductors

A series of nine precursors for pyrene-based biodegradable organic (semi)conductors having tetrasubstituted double bond as a central organic core and photo- or redox active centers attached at this core were investigated electrochemically in aprotic media at various electrodes. The influence of individual parts of the molecule on the redox properties were determined, the radical intermediates were intercepted using in situ EPR spectroelectrochemical experiments, the respective mechanisms were discussed, the difference between the first oxidation and the first reduction potential, respectively, were determined, and the experimental data were correlated with quantum chemical calculations.