title: Benzodicarbomethoxytetrathiafulvalene derivatives as soluble organic semiconductors.
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) cm(2) V(-1) s(-1)).
authors.affiliation: Institut de Ciència de Materials de Barcelona (ICMAB-CSIC) and Networking Research Center on Bioengineering, Biomaterials and Nanomedicine (CIBER-BBN), Campus de la Universitat Autònoma de Barcelona, Bellaterra E-08193 Barcelona, Spain.
authors.forename: Francisco
authors.initials: F
authors.lastname: Otón
authors.forename: Raphael
authors.initials: R
authors.lastname: Pfattner
authors.forename: Neil S
authors.initials: NS
authors.lastname: Oxtoby
authors.forename: Marta
authors.initials: M
authors.lastname: Mas-Torrent
authors.forename: Klaus
authors.initials: K
authors.lastname: Wurst
authors.forename: Xavier
authors.initials: X
authors.lastname: Fontrodona
authors.forename: Yoann
authors.initials: Y
authors.lastname: Olivier
authors.forename: Jérôme
authors.initials: J
authors.lastname: Cornil
authors.forename: Jaume
authors.initials: J
authors.lastname: Veciana
authors.forename: Concepció
authors.initials: C
authors.lastname: Rovira
mesh_terms: D018360:Crystallography, X-Ray; D004583:Electrons; D006573:Heterocyclic Compounds, 1-Ring / Q000737:chemistry*; D008958:Models, Molecular; D012666:Semiconductors; D012995:Solubility; D013056:Spectrophotometry, Ultraviolet; D013876:Thiophenes / Q000737:chemistry; D014961:X-Ray Diffraction
chemical_list: D006573:Heterocyclic Compounds, 1-Ring; D013876:Thiophenes; C544197:tetrathiafulvalene-2-carboxylic acid