Benzodicarbomethoxytetrathiafulvalene derivatives as soluble organic semiconductors

Francisco Otón, Raphael Pfattner, Neil S. Oxtoby, Marta Mas-Torrent, Klaus Wurst, Xavier Fontrodona, Yoann Olivier, Jérôme Cornil, Jaume Veciana, Concepció Rovira

Research output: Contribution to journalArticle

Abstract

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).

Original languageEnglish
Pages (from-to)154-163
Number of pages10
JournalJournal of Organic Chemistry
Volume76
Issue number1
DOIs
Publication statusPublished - 7 Jan 2011
Externally publishedYes

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    Otón, F., Pfattner, R., Oxtoby, N. S., Mas-Torrent, M., Wurst, K., Fontrodona, X., Olivier, Y., Cornil, J., Veciana, J., & Rovira, C. (2011). Benzodicarbomethoxytetrathiafulvalene derivatives as soluble organic semiconductors. Journal of Organic Chemistry, 76(1), 154-163. https://doi.org/10.1021/jo101817j