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Issue 29, 2014
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Dicyanobenzene and dicyanopyrazine derived X-shaped charge-transfer chromophores: comparative and structure–property relationship study

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Abstract

A series of novel X-shaped push–pull compounds based on benzene-1,2-dicarbonitrile has been designed, synthesized and further investigated by X-ray analysis, electrochemistry, absorption and emission spectra, SHG experiment and quantum-chemical calculations. The obtained data were compared with those for isolobal 5,6-disubstituted pyrazine-2,3-dicarbonitriles. Structure–property relationships were elucidated. The extension, composition and planarization of the π-linker used as well as the electron-withdrawing ability of both dicyano-substituted acceptor units affect the linear and nonlinear properties of the target charge-transfer chromophores most significantly.

Graphical abstract: Dicyanobenzene and dicyanopyrazine derived X-shaped charge-transfer chromophores: comparative and structure–property relationship study

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Supplementary files

Article information


Submitted
02 May 2014
Accepted
03 Jun 2014
First published
03 Jun 2014

This article is Open Access

Org. Biomol. Chem., 2014,12, 5517-5527
Article type
Paper

Dicyanobenzene and dicyanopyrazine derived X-shaped charge-transfer chromophores: comparative and structure–property relationship study

L. Dokládalová, F. Bureš, W. Kuznik, I. V. Kityk, A. Wojciechowski, T. Mikysek, N. Almonasy, M. Ramaiyan, Z. Padělková, J. Kulhánek and M. Ludwig, Org. Biomol. Chem., 2014, 12, 5517
DOI: 10.1039/C4OB00901K

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