Aromaticity of acenes: the model of migrating π-circuits

Dariusz W. Szczepanik , Miquel Sola , Tadeusz Marek Krygowski , Halina Szatyłowicz , Marcin Andrzejak , Barbara Pawełek , Justyna Dominikowska , Mercedes Kukułka , Karol Dyduch

Abstract

In this work we extend the concept of migrating Clar's sextets to explain local aromaticity trends in linear acenes predicted by theoretical calculations and experimental data. To assess the link between resonance and reactivity and to rationalize the constant-height AFM image of pentacene we used the electron density of delocalized bonds and other functions of the one-electron density from conceptual density functional theory. The presented results provide evidence for migration of Clar's π-sextets and larger circuits in these systems, and clearly show that the link between the theoretical concept of aromaticity and the real electronic structure entails the separation of intra- and inter-ring resonance effects, which in the case of [n]acenes (n = 3, 4, 5) comes down to solving a system of simple linear equations.
Author Dariusz W. Szczepanik
Dariusz W. Szczepanik,,
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, Miquel Sola
Miquel Sola,,
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, Tadeusz Marek Krygowski
Tadeusz Marek Krygowski,,
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, Halina Szatyłowicz (FC / DPC)
Halina Szatyłowicz,,
- Department Of Physical Chemistry
, Marcin Andrzejak
Marcin Andrzejak,,
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, Barbara Pawełek
Barbara Pawełek,,
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, Justyna Dominikowska
Justyna Dominikowska,,
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, Mercedes Kukułka
Mercedes Kukułka,,
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, Karol Dyduch
Karol Dyduch,,
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Journal seriesPhysical Chemistry Chemical Physics, ISSN 1463-9076, (A 40 pkt)
Issue year2018
Vol20
No19
Pages13430-13436
Publication size in sheets0.5
DOIDOI:10.1039/C8CP01108G
URL https://pubs.rsc.org/en/content/articlelanding/2018/cp/c8cp01108g#!divAbstract
Languageen angielski
File
c8cp01108g.pdf 1.85 MB
Score (nominal)40
ScoreMinisterial score = 40.0, 24-07-2018, ArticleFromJournal
Ministerial score (2013-2016) = 40.0, 24-07-2018, ArticleFromJournal
Publication indicators WoS Impact Factor: 2016 = 4.123 (2) - 2016=4.242 (5)
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