Issue 37, 2013
From the journal:

Organic & Biomolecular Chemistry

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

A. Belén Marco,a   Raquel Andreu,*a   Santiago Franco,a   Javier Garín,a   Jesús Orduna,a   Belén Villacampa,b   Beatriz E. Diosdado,c   Juan T. López Navarreted  and  Juan Casadod  

* Corresponding authors

a Departamento de Química Orgánica, ICMA, Universidad de Zaragoza-CSIC, 50009 Zaragoza, Spain
E-mail: randreu@unizar.es

b Departamento de Física de la Materia Condensada, ICMA, Universidad de Zaragoza-CSIC, 50009 Zaragoza, Spain

c Servicio de Difracción de Rayos X y Análisis por Fluorescencia, ICMA, Universidad de Zaragoza-CSIC, 50009 Zaragoza, Spain

d Departamento de Química Física, Universidad de Málaga, 29071 Málaga, Spain

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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Article information

DOI
https://doi.org/10.1039/C3OB41278D
Article type
Paper
Submitted
20 Jun 2013
Accepted
29 Jul 2013
First published
30 Jul 2013

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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