title: Bis(methylthio)tetracenes: synthesis, crystal-packing structures, and OFET properties.
abstract: 5,12-Bis(methylthio)tetracene (2) and 5,11-bis(methylthio)tetracene (3) were synthesized. DFT calculations indicate that the HOMO and LUMO energy levels of 2 and 3 are lowered by 0.13-0.24 eV and their HOMO-LUMO energy gaps are reduced by 0.1 eV relative to those of tetracene. X-ray crystallographic data revealed that 2 is arranged as a result of a 1-D slipped-cofacial π-stacking with S-S and S-π interactions, similar to the packing arrangement of 6,13-bis(methylthio)pentacene (1), whereas 3 exhibits a herringbone packing arrangement without S-S interactions. The OFET devices fabricated using spin-coated films of soluble 1 and 2, with a bottom-contact device configuration, exhibited hole mobilities as high as 1.3 × 10(-2) and 4.0 × 10(-2) cm(2) V(-1) s(-1) with current on/off ratios of over 10(5) and 10(4), respectively.
authors.affiliation: Department of Chemistry, Faculty of Science, Shizuoka University, 836 Ohya, Suruga-ku, Shizuoka 422-8529, Japan.
authors.forename: Takakazu
authors.initials: T
authors.lastname: Kimoto
authors.forename: Kenro
authors.initials: K
authors.lastname: Tanaka
authors.forename: Masatoshi
authors.initials: M
authors.lastname: Kawahata
authors.forename: Kentaro
authors.initials: K
authors.lastname: Yamaguchi
authors.forename: Saika
authors.initials: S
authors.lastname: Otsubo
authors.forename: Yoshimasa
authors.initials: Y
authors.lastname: Sakai
authors.forename: Yuuki
authors.initials: Y
authors.lastname: Ono
authors.forename: Akira
authors.initials: A
authors.lastname: Ohno
authors.forename: Kenji
authors.initials: K
authors.lastname: Kobayashi
mesh_terms: D018360:Crystallography, X-Ray; D008745:Methylation; D018625:Microscopy, Atomic Force; D008958:Models, Molecular; D008968:Molecular Conformation; D009279:Naphthacenes / Q000138:chemical synthesis*; D013438:Sulfhydryl Compounds / Q000737:chemistry*
chemical_list: D009279:Naphthacenes; D013438:Sulfhydryl Compounds