Donor/Acceptor Substituted Oligothiophenes: Synthesis, Spectroscopic and Electrochemical Properties

Abstract

Seven new donor/acceptor oligothiophenes 1-2 were synthesized by Stille coupling in moderate to good yields. Compounds 1-2 were completely characterized by the usual spectroscopic methods. In agreement with the electrochemical and the spectroscopic studies for this compounds the new derivatives prepared, can find application for manufacturing new materials with strong non-linear optical (NLO) properties.

Thienylpyrrole azo dyes: synthesis, solvatochromic and electrochemical properties

“…[6][7] Recently we have also demonstrated that donor-acceptor substituted bithiophenes and terthiophenes have many favorable features as NLO materials. [8][9][10][11] Use of conjugated thiophene and pyrrole derivatives as donors combined with substituted acceptor groups are promising candidates among such D-A systems due to their numerous applications. Unlike the thiophene or furan analogues, the pyrrole ring can be further substituted at the nitrogen atom so that the electron density of the chromophore can be changed.…”

Donor-Acceptor Substituted Thienylpyrrole Azo Dyes: Synthesis, Solvatochromic and Electrochemical Properties

“…Azo dyes have particular interest because they can be readily prepared with a wide range of donor and acceptor groups and also because the planarity of the azo bridge versus the nonplanarity of stilbenes or other systems should contribute to the larger π electron transmission effects and lead to higher optical activity [3][4]. As part of our continuing interest in non-linear optical material [5][6][7][8][9][10][11], we report in this paper the synthesis the solvatochromic and the electrochemical studies of new 1-alkyl(aryl)-2-(2´-thienyl)-5-phenylazopyrrole derivatives 1-2 which have the para NO 2 and the ortho-para NO 2 groups as the electron-withdrawing groups on the phenylazo moiety and the conjugated 1-alkyl(aryl)-2-(2´-thienyl)pyrrole, as strong π-electron donor moieties.…”

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

“…[20][21][22][23][24]30 Therefore, tricyanovinyl-derivatives 1 represent promising candidates for NLO and other applications. As part of our continuing interest in non-linear optical material [13][14][15][16][31][32] we have synthesized new tricyanovinyl-substituted thienylpyrroles 1, by tricyanovinylation reaction of thienylpyrroles 2 described by us recently. 33 …”

“…[4][5][6][7][8][9][10][11][12] Recently we have also demonstrated that donor-acceptor substituted bithiophenes and terthiophenes have many favorable features as NLO materials. [13][14][15][16] Conjugated thiophene and pyrrole derivatives as donors combined with substituted acceptor groups are promising candidates among such D-A systems due to their numerous applications. Unlike the thiophene or furane analogues, the pyrrole ring can be further substituted on the nitrogen atom so that the electron density of the chromophore can be changed.…”