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Issue 37, 2013
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Push–pull systems bearing a quinoid/aromatic thieno[3,2-b]thiophene moiety: synthesis, ground state polarization and second-order nonlinear properties

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Abstract

Chromophores bearing a 2-dicyanomethylenethieno[3,2-b]thiophene moiety in their quinoidal form have been synthesized, exploring for the first time the reactivity of this system towards aldehydes. Their ground state polarization and linear and second-order nonlinear optical (NLO) properties have been determined by a combined experimental and theoretical study, and compared to those of analogous compounds featuring an aromatic thienothiophene unit. Due to the gaining of aromaticity, quinoid systems have been found to display more polarized electronic ground states and higher NLO responses with respect to their aromatic counterparts.

Graphical abstract: Push–pull systems bearing a quinoid/aromatic thieno[3,2-b]thiophene moiety: synthesis, ground state polarization and second-order nonlinear properties

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Publication details

The article was received on 20 Jun 2013, accepted on 29 Jul 2013 and first published on 30 Jul 2013


Article type: Paper
DOI: 10.1039/C3OB41278D
Citation: Org. Biomol. Chem., 2013,11, 6338-6349
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    Push–pull systems bearing a quinoid/aromatic thieno[3,2-b]thiophene moiety: synthesis, ground state polarization and second-order nonlinear properties

    A. B. Marco, R. Andreu, S. Franco, J. Garín, J. Orduna, B. Villacampa, B. E. Diosdado, J. T. López Navarrete and J. Casado, Org. Biomol. Chem., 2013, 11, 6338
    DOI: 10.1039/C3OB41278D

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