title: HOMO stabilisation in π-extended dibenzotetrathiafulvalene derivatives for their application in organic field-effect transistors.
abstract: Three new organic semiconductors, in which either two methoxy units are directly linked to a dibenzotetrathiafulvalene (DB-TTF) central core and a 2,1,3-chalcogendiazole is fused on the one side, or four methoxy groups are linked to the DB-TTF, have been synthesised as active materials for organic field-effect transistors (OFETs). Their electrochemical behaviour, electronic absorption and fluorescence emission as well as photoinduced intramolecular charge transfer were studied. The electron-withdrawing 2,1,3-chalcogendiazole unit significantly affects the electronic properties of these semiconductors, lowering both the HOMO and LUMO energy levels and hence increasing the stability of the semiconducting material. The solution-processed single-crystal transistors exhibit high performance with a hole mobility up to 0.04 cm(2)  V(-1)  s(-1) as well as good ambient stability.
authors.affiliation: Departement für Chemie und Biochemie, Universität Bern, Freiestrasse 3, 3012 Bern (Switzerland), Fax: (+41) 31-631-3995.
authors.forename: Yan
authors.initials: Y
authors.lastname: Geng
authors.forename: Raphael
authors.initials: R
authors.lastname: Pfattner
authors.forename: Antonio
authors.initials: A
authors.lastname: Campos
authors.forename: Wei
authors.initials: W
authors.lastname: Wang
authors.forename: Olivier
authors.initials: O
authors.lastname: Jeannin
authors.forename: Jürg
authors.initials: J
authors.lastname: Hauser
authors.forename: Joaquim
authors.initials: J
authors.lastname: Puigdollers
authors.forename: Stefan T
authors.initials: ST
authors.lastname: Bromley
authors.forename: Silvio
authors.initials: S
authors.lastname: Decurtins
authors.forename: Jaume
authors.initials: J
authors.lastname: Veciana
authors.forename: Concepció
authors.initials: C
authors.lastname: Rovira
authors.forename: Marta
authors.initials: M
authors.lastname: Mas-Torrent
authors.forename: Shi-Xia
authors.initials: SX
authors.lastname: Liu
mesh_terms: D001555:Benzene Derivatives / Q000737:chemistry*; D004583:Electrons; D005453:Fluorescence; D006571:Heterocyclic Compounds / Q000737:chemistry*; D012666:Semiconductors; D014173:Transistors, Electronic
chemical_list: D001555:Benzene Derivatives; D006571:Heterocyclic Compounds; C063887:tetrathiafulvalene
keywords: donor-acceptor systems; fused-ring systems; molecular electronics; semiconductors; thin films