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Benzodicarbomethoxytetrathiafulvalene Derivatives as Soluble Organic Semiconductors

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posted on 2011-01-07, 00:00 authored by Francisco Otón, Raphael Pfattner, Neil S. Oxtoby, Marta Mas-Torrent, Klaus Wurst, Xavier Fontrodona, Yoann Olivier, Jérôme Cornil, Jaume Veciana, Concepció Rovira
A series of new tetrathiafulvalene (TTF) derivatives bearing dimethoxycarbonyl and phenyl or phthalimidyl groups fused to the TTF core (6 and 1518) 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).