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Tetrabenzoperipentacene: Stable Five‐Electron Donating Ability and a Discrete Triple‐Layered β‐Graphite Form in the Solid State
Author(s) -
Matsumoto Akinobu,
Suzuki Mitsuharu,
Kuzuhara Daiki,
Hayashi Hironobu,
Aratani Naoki,
Yamada Hiroko
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201502466
Subject(s) - graphite , ring (chemistry) , stacking , conjugated system , electron , materials science , crystallography , fullerene , molecule , cluster (spacecraft) , triple bond , cyclic voltammetry , carbon fibers , chemistry , polymer chemistry , electrochemistry , organic chemistry , composite material , physics , electrode , quantum mechanics , composite number , computer science , programming language , polymer , double bond
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 C 60 in terms of stable multicharge‐storage nanocarbon materials.