N,N′-Dicyanoquinone Diimide-Derived Donor–Acceptor Chromophores: Conformational Analysis and Optoelectronic Properties

A formal [2 + 2] cycloaddition–cycloreversion (CA–CR) between N,N′-dicyanoquinone diimides (DCNQIs) and electron-rich alkynes was explored, providing a new class of π-conjugated donor–acceptor chromophores. These DCNQI adducts exist in the solid state as single diastereoisomers, but as two interconv...

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Bibliographic Details
Published in:Organic letters 2012-01, Vol.14 (1), p.54-57
Main Authors: Chiu, Melanie, Jaun, Bernhard, Beels, Marten T. R, Biaggio, Ivan, Gisselbrecht, Jean-Paul, Boudon, Corinne, Schweizer, W. Bernd, Kivala, Milan, Diederich, François
Format: Article
Language:English
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Summary:A formal [2 + 2] cycloaddition–cycloreversion (CA–CR) between N,N′-dicyanoquinone diimides (DCNQIs) and electron-rich alkynes was explored, providing a new class of π-conjugated donor–acceptor chromophores. These DCNQI adducts exist in the solid state as single diastereoisomers, but as two interconverting diastereoisomers in solution. Solid- and solution-state evidence for intramolecular charge transfer (CT) was obtained; additionally, the DCNQI adducts exhibit positive solvatochromism and significant solution-state third-order polarizabilities.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol202815q