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Title

Benzodicarbomethoxytetrathiafulvalene derivatives as soluble organic semiconductors

AuthorsOtón, Francisco ; Pfattner, Raphael ; Oxtoby, Neil S. ; Mas Torrent, Marta ; Wurst, Klaus; Fontrodona, Xavier; Olivier, Yoann; Cornil, Jérôme; Veciana, Jaume ; Rovira, Concepció
KeywordsDithiophene-tetrathiafulvalene
High-mobility
Charge-transsport
Extended tetrathialfulvalene derivatives
Field-effect transistors
Energy
Single-crystals
Intermolecular interactions
Photophysical properties
Electron-transfer
Issue Date7-Jan-2011
PublisherAmerican Chemical Society
CitationJournal of Organic Chemistry 76(1): 154-163 (2011)
AbstractA 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.
URIhttp://hdl.handle.net/10261/102932
DOI10.1021/jo101817j
Identifiersdoi: 10.1021/jo101817j
issn: 0022-3263
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