Tuning of the Electronic and Optical Properties of Oligothiophenes via Cyano Substitution:  A Joint Experimental and Theoretical Study

• Published in: The journal of physical chemistry. B Vol. 101; no. 23; pp. 4553 - 4558
• Main Authors: Demanze, Frédéric, Cornil, Jérôme, Garnier, Francis, Horowitz, Gilles, Valat, Pierre, Yassar, Abderrahim, Lazzaroni, Roberto, Brédas, Jean-Luc
• Format: Journal Article
• Language: English
• Published: American Chemical Society 05.06.1997
• ISSN: 1520-6106; 1520-5207
• DOI: 10.1021/jp970085z

Cyano-substituted bi- and terthiophene derivatives have been synthesized and characterized both electrochemically and optically. The experimental data are compared to the results of quantum-chemical calculations in order to rationalize the evolution of the frontier levels of the thiophene oligomers as a function of the number and position of the cyano substituents. This issue is of particular relevance in the context of organic light-emitting diodes and field-effect transistors to determine the substitution pattern required for the design of efficient electron-transporting (n-type) oligothiophene derivatives. The experimental and theoretical results demonstrate that the cyano functionalization allows for a fine-tuning of the electronic and optical properties of the thiophene compounds.