Benzodicarbomethoxytetrathiafulvalene derivatives as soluble organic semiconductors

A series of new tetrathiafulvalene (TTF) derivatives bearing dimethoxycarbonyl and phenyl or phthalimidyl groups fused to the TTF core (6 and 15-18) has been synthesized as potential soluble semiconductor materials for organic field-effect transistors (OFETs). The electron-withdrawing substituents lower the energy of the HOMO and LUMO levels and increase the solubility and stability of the semiconducting material. Crystal structures of all new TTF derivatives are also described, and theoretical DFT calculations were carried out to study the potential of the crystals to be used in OFET. In the experimental study, the best performing device exhibited a hole mobility up to 7.5 × 10-3 cm2 V-1 s-1). © 2010 American Chemical Society.EU by the EC FP7 ONE-P large-scale project (no. 212311), Marie Curie EST FuMASSEC, DGI, Spain (Contract Nos.CTQ2006-06333/BQU and CTQ2010-19501/BQU), Generalitat de Catalunya, (2009SGR00516), and the programme “Juan de la Cierva”(MICINN). We also thank Stefan T. Bromley for his advice regarding the DFT calculations and CESGA for the use of their installations. The work in Mons is also supported by the European ONE-P project as well as by the Belgian National Fund for Scientific Research (FNRS). Y.O. and J.C. are FNRS research fellows.Peer Reviewe