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Aromaticity Relocation in Perylene Derivatives upon Two-Electron Oxidation To Form Anthracene and Phenanthrene

Authors :
Hironobu Hayashi
Junpei Yuasa
Akinobu Matsumoto
Mitsuharu Suzuki
Daiki Kuzuhara
Hiroko Yamada
Naoki Aratani
Tsuyoshi Kawai
Source :
Chemistry (Weinheim an der Bergstrasse, Germany). 22(41)
Publication Year :
2016

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.

Details

ISSN :
15213765
Volume :
22
Issue :
41
Database :
OpenAIRE
Journal :
Chemistry (Weinheim an der Bergstrasse, Germany)
Accession number :
edsair.doi.dedup.....cef065c889196aa7145c69035b80772e