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Synthesis of tricyanovinyl-substituted thienylpyrroles and characterization of the solvatochromic, electrochemical and non-linear optical properties |
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| Authors: | M. Manuela M. Raposo Ana M.R.C. Sousa F. Ferreira E. de Matos Gomes |
| Affiliation: | a Centro de Química, Universidade do Minho, Campus de Gualtar, 4710‐057 Braga, Portugal b Laboratoire d'Ingénierie Moléculaire et Biochimie Pharmacologique, UFR SciFA, Université de Metz, 1, Boulevard Arago, Metz Technopôle, 57078 Metz Cedex 3, France c Departamento de Física, Universidade do Minho, Campus de Gualtar, 4710‐057 Braga, Portugal |
| 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. |
| Keywords: | Tricyanovinylation Donor-acceptor thienylpyrroles Chromophores Solvatochromism Electrochemistry Hyper-Rayleigh scattering (HRS) Non-linear optical (NLO) material |
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