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

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

Research output: Contribution to journalArticle

11 Citations (Scopus)

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 2008
Externally publishedYes

Fingerprint

Tin
Fluorides
Coloring Agents
Dyes
Salts
Ions
tributyltin
VPM chloride
benzothiazole

Keywords

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

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., & 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

A novel synthetic route to thiacyanine dyes containing a perfluorinated polymethine chain. / Yagupolskii, L. M.; Kondratenko, N. V.; Chernega, O. I.; Chernega, A. N.; Buth, Sergii; Yagupolskii, Yu L.

In: Dyes and Pigments, Vol. 79, No. 3, 12.2008, p. 242-246.

Research output: Contribution to journalArticle

Yagupolskii, LM, Kondratenko, NV, Chernega, OI, Chernega, AN, Buth, S & Yagupolskii, YL 2008, 'A novel synthetic route to thiacyanine dyes containing a perfluorinated polymethine chain', Dyes and Pigments, vol. 79, no. 3, pp. 242-246. https://doi.org/10.1016/j.dyepig.2008.03.003
Yagupolskii LM, Kondratenko NV, Chernega OI, Chernega AN, Buth S, Yagupolskii YL. A novel synthetic route to thiacyanine dyes containing a perfluorinated polymethine chain. Dyes and Pigments. 2008 Dec;79(3):242-246. https://doi.org/10.1016/j.dyepig.2008.03.003
Yagupolskii, L. M. ; Kondratenko, N. V. ; Chernega, O. I. ; Chernega, A. N. ; Buth, Sergii ; Yagupolskii, Yu L. / A novel synthetic route to thiacyanine dyes containing a perfluorinated polymethine chain. In: Dyes and Pigments. 2008 ; Vol. 79, No. 3. pp. 242-246.
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