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Wiley-VCH Verlag, ChemInform, 12(37), 2006

DOI: 10.1002/chin.200612115

Elsevier, Tetrahedron, 50(61), p. 11991-11998

DOI: 10.1016/j.tet.2005.09.062

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Synthesis of tricyanovinyl-substituted thienylpyrroles and characterization of the solvatochromic, electrochemical and non-linear optical properties

Journal article published in 2005 by M. Manuela M. Raposo ORCID, Ana M. R. C. Sousa, G. Kirsch, E. de Matos Gomes, F. Ferreira, M. Belsley ORCID, E. Matos Gomes, E. de Matos Gomes, A. Maurício C. Fonseca ORCID, A. Maurício C. Fonseca
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Abstract

Tricyanovinyl-substituted 1-(alkyl)aryl-2-(2´-thienyl)pyrroles 1 have been synthesized by direct tricyanovinylation reaction of 1-(alkyl)aryl-2-(2´-thienyl)pyrroles 2 using TCNE. The tricyanovinyl- derivatives 1 display dramatic reductions in both their optical and electrochemical band gaps relative to thienylpyrrole precursors 2. The solvatochromic behavior of compounds 1 was investigated in a variety of solvents. Hyper-Rayleigh scattering was used to measure the first hyperpolarizabilities β of the mentioned compounds. The β values show that the new compounds prepared could be used on the manufacture of materials with good non-linear (NLO) properties.