A novel synthetic route to thiacyanine dyes containing a perfluorinated polymethine chain

L. M. Yagupolskii, N. V. Kondratenko, O. I. Chernega, A. N. Chernega, S. A. Buth, Yu L. Yagupolskii

Research output: Contribution to journalArticle

12 Scopus citations

Abstract

2-Iodobenzothiazole was reacted with tributyl(trifluorovinyl)tin and (2-chlorodifluorovinyl)tributyltin by the Stille reaction to yield 2-trifluorovinyl- and 2-(2-chlorodifluorovinyl)benzothiazole, respectively. The quaternary salt of 2-trifluorovinylbenzothiazole, when treated with fluoride ion, furnished the corresponding thiacarbocyanine dye containing a perfluorinated polymethine chain. The reaction involved nontrivial cleavage of the C-C bond to provide an energetically advantageous conjugated perfluoropolyenic system.

Original languageEnglish (US)
Pages (from-to)242-246
Number of pages5
JournalDyes and Pigments
Volume79
Issue number3
DOIs
StatePublished - Dec 1 2008

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Keywords

  • 2-Trifluorovinylbenzothiazole
  • Fluoride ion
  • Perfluorinated polymethine chain
  • Thiacarbocyanine dye
  • α,β-Difluorosubstituted dyes

ASJC Scopus subject areas

  • Chemical Engineering(all)
  • Process Chemistry and Technology

Cite this

Yagupolskii, L. M., Kondratenko, N. V., Chernega, O. I., Chernega, A. N., Buth, S. A., & Yagupolskii, Y. L. (2008). A novel synthetic route to thiacyanine dyes containing a perfluorinated polymethine chain. Dyes and Pigments, 79(3), 242-246. https://doi.org/10.1016/j.dyepig.2008.03.003