title: Aromaticity Relocation in Perylene Derivatives upon Two-Electron Oxidation To Form Anthracene and Phenanthrene.
abstract: We prepared perylene dications 1(2+) and 2(2+) by using "capped" perylene derivatives, and for the first time, successfully obtained single crystals of a perylene dication 1(2+) that enabled us to perform its structural analysis. We realized that the substituted aryl groups on perylene control the positions of positive charges, thus the remaining electronic system satisfies Clar's sextet rule toward the highest number of localized sextets. Experimental and theoretical evidence proved that Clar's aromatic π-sextet rule could be applied even for the dicationic perylenes in a very simple way.
authors.affiliation: Graduate School of Materials Science, Nara Institute of Science and Technology (NAIST), 8916-5 Takayama-cho, Ikoma, 630-0192, Japan.
authors.forename: Akinobu
authors.initials: A
authors.lastname: Matsumoto
authors.affiliation: Graduate School of Materials Science, Nara Institute of Science and Technology (NAIST), 8916-5 Takayama-cho, Ikoma, 630-0192, Japan.
authors.forename: Mitsuharu
authors.initials: M
authors.lastname: Suzuki
authors.affiliation: Graduate School of Materials Science, Nara Institute of Science and Technology (NAIST), 8916-5 Takayama-cho, Ikoma, 630-0192, Japan.
authors.forename: Hironobu
authors.initials: H
authors.lastname: Hayashi
authors.affiliation: Graduate School of Materials Science, Nara Institute of Science and Technology (NAIST), 8916-5 Takayama-cho, Ikoma, 630-0192, Japan.
authors.forename: Daiki
authors.initials: D
authors.lastname: Kuzuhara
authors.affiliation: Graduate School of Materials Science, Nara Institute of Science and Technology (NAIST), 8916-5 Takayama-cho, Ikoma, 630-0192, Japan.
authors.forename: Junpei
authors.initials: J
authors.lastname: Yuasa
authors.affiliation: Graduate School of Materials Science, Nara Institute of Science and Technology (NAIST), 8916-5 Takayama-cho, Ikoma, 630-0192, Japan.
authors.forename: Tsuyoshi
authors.initials: T
authors.lastname: Kawai
authors.affiliation: Graduate School of Materials Science, Nara Institute of Science and Technology (NAIST), 8916-5 Takayama-cho, Ikoma, 630-0192, Japan. aratani@ms.naist.jp.
authors.forename: Naoki
authors.initials: N
authors.lastname: Aratani
authors.affiliation: Graduate School of Materials Science, Nara Institute of Science and Technology (NAIST), 8916-5 Takayama-cho, Ikoma, 630-0192, Japan. hyamada@ms.naist.jp.
authors.forename: Hiroko
authors.initials: H
authors.lastname: Yamada
keywords: aromaticity; bond length alternation; dication; oxidation; perylene