title: Tetrabenzoperipentacene: Stable Five-Electron Donating Ability and a Discrete Triple-Layered β-Graphite Form in the Solid State.
abstract: An oxidative ring-closure reaction of a tetranaphthylpyrene derivative led to the synthesis of a 56 all-carbon conjugated tetrabenzoperipentacene. In the single-crystal X-ray structure, three molecules make a triple-layered cluster by π-stacking, wherein each layer rotates by 120°, and is thus considered a petit β-graphite. As for the optical properties, the Stokes shift is extremely small (10 cm(-1) ), thus indicating its remarkably rigid framework. The tetrabenzoperipentacene exhibits reversible five-electron oxidation waves in cyclic voltammetry, and is regarded as a counterpart to the fullerene C60 in terms of stable multicharge-storage nanocarbon materials.
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: 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: 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). 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.|CREST, Japan Science and Technology Agency (JST), 4-1-8 Honcho, Kawaguchi, Saitama 332-0012 (Japan). hyamada@ms.naist.jp.
authors.forename: Hiroko
authors.initials: H
authors.lastname: Yamada
keywords: aromaticity; graphene; oxidation; polycycles; π interactions