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Aromaticity Relocation in Perylene Derivatives upon Two‐Electron Oxidation To Form Anthracene and Phenanthrene
Author(s) -
Matsumoto Akinobu,
Suzuki Mitsuharu,
Hayashi Hironobu,
Kuzuhara Daiki,
Yuasa Junpei,
Kawai Tsuyoshi,
Aratani Naoki,
Yamada Hiroko
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201602188
Subject(s) - phenanthrene , anthracene , perylene , aromaticity , photochemistry , pyrene , electron , chemistry , relocation , organic chemistry , molecule , physics , computer science , nuclear physics , programming language
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.