Synthesis and Electrochemical and Computational Analysis of Two New Families of Thiophene-Carbonyl Molecules

Two oligomeric families of materials containing thiophene-carbonyl and thiophene-dicarbonyl units have been synthesized and characterized with emphasis on structural, electrochemical, and electronic properties. Three thiophene-carbonyl derivatives containing 1, 2, and 3 carbonyl groups exhibited one, two, and three one-electron reversible reduction processes, respectively. On the other hand, three thiophene-dicarbonyl derivatives exhibited two, four, and six reversible reduction processes, respectively. The electrochemical stability of these materials derives from the existence of the various anionic species, monoanion, dianion, trianion, and so forth, respectively, in the form of enolate anions. Single crystals and density functional theory models of typical structures were obtained and compared to investigate the electronic properties of the two series of molecules. The exhibited electrochemical characters endowed these structures with a potential application prospect in the field of electrical energy storage.