Structural and electronic properties of poly(3-thiophen-3-yl-acrylic acid)

This work presents a combined theoretical and experimental study of poly(3-thiophene-3-yl acrylic acid), a new polythiophene derivative soluble in polar solvents. Quantum chemical calculations on small oligomers were performed to propose a structural model for this polymer. Specifically, the minimum energy conformations and the rotational profiles of the different isomeric derivatives constructed for a model system formed by two monomeric units were calculated. The resulting model, which shows head-to-tail polymer linkages and the acrylic acid side group arranged in trans-conformation, were used to predict the π–π∗ lowest transition energy of an infinite polymer chain. On the other hand, the polymer was prepared by chemical oxidative coupling using anhydrous ferric chloride and subsequent alkaline hydrolysis. The synthetized material, which is soluble in aqueous base and acetone solutions, was characterized by FTIR, 1H NMR and UV–vis experiments. Both the structural information and electronic properties derived from such experiments are fully consistent with the theoretical model obtained using quantum mechanical calculations.