Cruciform Alkynylated Anthanthrene Derivatives: A Structure–Properties Relationship Case Study

An efficient and versatile synthetic strategy toward cruciform anthanthrene compounds using Sonogashira couplings steps was developed. Acetylenic linkers were used to effectively extend the π-conjugation of polycyclic anthanthrone and anthanthrene compounds and tune their optoelectronic properties....

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Bibliographic Details
Published in:Journal of organic chemistry 2014-03, Vol.79 (6), p.2404-2418
Main Authors: Giguère, Jean-Benoît, Boismenu-Lavoie, Joël, Morin, Jean-François
Format: Article
Language:English
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Summary:An efficient and versatile synthetic strategy toward cruciform anthanthrene compounds using Sonogashira couplings steps was developed. Acetylenic linkers were used to effectively extend the π-conjugation of polycyclic anthanthrone and anthanthrene compounds and tune their optoelectronic properties. Structure–property relationships supported by DFT calculations indicated more effective π-conjugation along the 6,12 axis than along the 4,10 axis. These molecules displayed strong J-aggregation both in solution and in the solid state and proved to be highly photostable with reversible redox processes, which are properties of interest in materials sciences.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo402674m