title: Synthesis of perfluoroalkylated pentacenes and evaluation of their fundamental physical properties.
abstract: Symmetrical and unsymmetrical pentacenes carrying two perfluoroalkyl (Rf) chains, at the 6 and 13 positions, were synthesized from easily available pentacene-6,13-quinone via facile three or four step reactions. After extensive evaluation, it was clearly found that the control of both the electron density of the aromatic rings on the pentacene core and molecular alignment in the crystalline state nicely affected their physical properties. Thus, we successfully prove in this article that (1) their anti-oxidation ability was significantly enhanced due to a decrease in the HOMO and LUMO energy and (2) a distinct difference in charge-transporting properties was observed between the symmetrical and unsymmetrical pentacenes.
authors.affiliation: Department of Applied Chemistry, Graduate School of Engineering, Tokyo University of Agriculture and Technology, 2-24-16 Nakamachi, Koganei 184-8588, Japan. tyamazak@cc.tuat.ac.jp.
authors.forename: Shigeyuki
authors.initials: S
authors.lastname: Yamada
authors.affiliation: Department of Applied Chemistry, Graduate School of Engineering, Tokyo University of Agriculture and Technology, 2-24-16 Nakamachi, Koganei 184-8588, Japan. tyamazak@cc.tuat.ac.jp.
authors.forename: Keita
authors.initials: K
authors.lastname: Kinoshita
authors.affiliation: Department of Applied Chemistry, Graduate School of Engineering, Tokyo University of Agriculture and Technology, 2-24-16 Nakamachi, Koganei 184-8588, Japan. tyamazak@cc.tuat.ac.jp.
authors.forename: Shota
authors.initials: S
authors.lastname: Iwama
authors.affiliation: Department of Applied Chemistry, Graduate School of Engineering, Tokyo University of Agriculture and Technology, 2-24-16 Nakamachi, Koganei 184-8588, Japan. tyamazak@cc.tuat.ac.jp.
authors.forename: Takashi
authors.identifier: http://orcid.org/0000-0002-1460-3086
authors.initials: T
authors.lastname: Yamazaki
authors.affiliation: Department of Biomolecular Functional Engineering, Ibaraki University, Nakanarusawa 4-12-1, Hitachi 316-8511, Japan.
authors.forename: Toshio
authors.initials: T
authors.lastname: Kubota
authors.affiliation: Department of Chemistry, Faculty of Science, Ochanomizu University, Otsuka, Bunkyo-ku, Tokyo 112-8610, Japan.
authors.forename: Tomoko
authors.initials: T
authors.lastname: Yajima
authors.affiliation: Research Center, Asahi Glass Co., Ltd., Hazawa-cho, Kanagawa-ku, Yokohama-shi, Kanagawa 221-8775, Japan.
authors.forename: Kyoko
authors.initials: K
authors.lastname: Yamamoto
authors.affiliation: Research Center, Asahi Glass Co., Ltd., Hazawa-cho, Kanagawa-ku, Yokohama-shi, Kanagawa 221-8775, Japan.
authors.forename: Shinya
authors.initials: S
authors.lastname: Tahara