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

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...

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Bibliographic Details
Main Author: Raposo, M. Manuela M. (author)
Other Authors: Sousa, Ana M. R. C. (author), Kirsch, G. (author), Ferreira, F. (author), Belsley, M. (author), Gomes, E. Matos (author), Fonseca, A. Maurício C. (author)
Format: article
Language:eng
Published: 2005
Subjects:
Online Access:http://hdl.handle.net/1822/7846
Country:Portugal
Oai:oai:repositorium.sdum.uminho.pt:1822/7846
Description
Summary: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.