title: A pi-stacking terthiophene-based quinodimethane is an n-channel conductor in a thin film transistor.
abstract: A terthiophene-based quinodimethane, 3',4'-dibutyl-5,5' '-bis(dicyanomethylene)-5,5' '-dihydro-2,2':5',2' '-terthiophene (1) was synthesized and crystallized. Compound 1 has a planar quinoid geometry that is stabilized by dicyanomethylene groups at each end of the molecule. In the crystal each molecule is part of a dimerized face-to-face pi-stack, with intermolecular spacings of 3.47 and 3.63 A, respectively. Cyclic voltammetry showed that 1 could be reversibly reduced and oxidized in methylene chloride solution. Thin film transistors (TFTs) were prepared by vacuum evaporation of 1 onto SiO2(300 nm)/Si substrates, followed by evaporation of Ag source and drain contacts. The doped Si substrate served as the gate electrode. X-ray diffraction and atomic force microscopy indicate the films are polycrystalline, with the long axes of the molecules approximately perpendicular to the substrate. The TFT measurements revealed n-channel conduction in films of 1, with room-temperature electron field effect mobilities as high as 0.005 cm2/Vs. The butyl side chains give 1 appreciable solubility in a range of common solvents, and preliminary TFT results on films cast from chlorobenzene show electron mobility as high as 0.002 cm2/Vs. These results indicate that pi-stacked quinoidal thiophene oligomers are a promising new class of soluble n-channel organic semiconductors.
authors.affiliation: Department of Chemistry, University of Minnesota, Minneapolis, Minnesota 55455, USA.
authors.forename: Ted M
authors.initials: TM
authors.lastname: Pappenfus
authors.forename: Reid J
authors.initials: RJ
authors.lastname: Chesterfield
authors.forename: C Daniel
authors.initials: CD
authors.lastname: Frisbie
authors.forename: Kent R
authors.initials: KR
authors.lastname: Mann
authors.forename: Juan
authors.initials: J
authors.lastname: Casado
authors.forename: Jonathan D
authors.initials: JD
authors.lastname: Raff
authors.forename: Larry L
authors.initials: LL
authors.lastname: Miller