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

[摘要] Tricyanovinyl-substituted 1-(alkyl)aryl-2-(2'-thienyl)pyrroles 1 have been synthesized by direct tricyanovinylation reaction of 1-(alkyl)aryi-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 beta of the mentioned compounds. The beta values show that the new compounds prepared could be used on the manufacture of materials with good non-linear (NLO) properties. (c) 2005 Elsevier Ltd. All rights reserved.

[发布日期] 2005-12-12

[关键词] tricyanovinylation;donor-acceptor thienylpyrroles;chromephores;solvatochromism;electrochemistry;hyper-Rayleigh scattering (HRS);non-linear optical (NLO) material