Electrochemical study of 1,3-indandione derivatives of terthiophenes

Properties and behavior of a group of four newly synthesized derivatives of terthiophene and terthienylenvinylene was studied. All four investigated monomers bear a 1,3-indandione substituent at the central thiophene ring and two of them (ThIV, ThIVM) have additional vinyl bonds introduced between the thiophene rings. In addition, ThIM and ThIVM have 5 positions of the two terminal rings blocked with methyl groups. The measurements were done using cyclic voltamperometry (CV) in solutions of 0.1M Bu4NBF4 in CH2Cl2. It was found that ThI and ThIV polymerise easily. CV of ThI reveals a reduction peak resulting probably from the abstraction of a proton. During polymerisation of ThIV a group of peaks is observed indicating its stepwise oxidation process. The polymerisation potential of ThIV was found to be lower than that of ThI which could mean that formation of radical-cation is easier in the former. Stability measurements indicated that polymer films of ThI are electrochemically stable in CH2Cl2 and films of ThIV are not. Efforts to polymerise ThIM and ThIVM failed. Their CVs revealed only peaks coming from oxidation of the monomers, some of which were semi-reversible.