title: Synthesis and Characterization of 6,13-Diamino-Substituted Pentacenes.
abstract: A series of 6,13-diamino-substituted pentacenes 1 a-d has been prepared and characterized as a new class of pentacene derivatives with strong donor ability and enhanced solubility in common organic solvents. The spectroelectrochemical and DFT studies revealed that the two-electron oxidation process was accompanied by the substantial structural change into a butterfly-like conformation of the pentacene moiety. More importantly, the extent of deformation from the planar pentacene moiety in the dications of 6,13-diaminopentacene is tunable by varying the N-substituents.
authors.affiliation: Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto, 615-8510, Japan. aito@scl.kyoto-u.ac.jp.
authors.forename: Akihiro
authors.initials: A
authors.lastname: Ito
authors.affiliation: Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto, 615-8510, Japan.
authors.forename: Masashi
authors.initials: M
authors.lastname: Uebe
authors.affiliation: Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto, 615-8510, Japan.
authors.forename: Kazuki
authors.initials: K
authors.lastname: Takahashi
authors.affiliation: Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto, 615-8510, Japan.
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Ishikawa
authors.affiliation: Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto, 615-8510, Japan.
authors.forename: Daisuke
authors.initials: D
authors.lastname: Sakamaki
authors.affiliation: X-ray Research Laboratory, Rigaku Corporation, Matsubara-cho 3-9-12, Akishima, Tokyo, 196-8666, Japan.
authors.forename: Hiroyasu
authors.initials: H
authors.lastname: Sato
authors.affiliation: X-ray Research Laboratory, Rigaku Corporation, Matsubara-cho 3-9-12, Akishima, Tokyo, 196-8666, Japan.
authors.forename: Takashi
authors.initials: T
authors.lastname: Matsumoto
authors.affiliation: Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto, 615-8510, Japan.
authors.forename: Kazuyoshi
authors.initials: K
authors.lastname: Tanaka
keywords: UV/Vis spectroscopy; density functional calculations; electrochemistry; pi interactions