Synthesis of tricyanovinyl-substituted thienylpyrroles and characterization of ...

• Author(s): Raposo, M. Manuela M. ; Sousa, Ana M. R. C. ; Kirsch, G. ; Ferreira, F. ; Belsley, M. ; Gomes, E. Matos ; Fonseca, A. Maurício C.
• Date: 2005
• Persistent ID: http://hdl.handle.net/1822/7846
• Origin: RepositóriUM - Universidade do Minho
• Subject(s): Pyrroles; Thiophenes; Donor-acceptor thienylpyrroles; Tricyanovinylation; Chromophores; Solvatochromism; Electrochemistry; Hyper-Rayleigh scattering (HRS); Non-linear optical (NLO) material
• Document Type: Article
• Language: English

Description

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.