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

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 thos...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2014-08, Vol.12 (29), p.5517-5527
Main Authors: Dokládalová, L, Bureš, F, Kuznik, W, Kityk, I V, Wojciechowski, A, Mikysek, T, Almonasy, N, Ramaiyan, M, Padělková, Z, Kulhánek, J, Ludwig, M
Format: Article
Language:English
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Summary: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.
ISSN:1477-0520
1477-0539
DOI:10.1039/c4ob00901k