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

doi:10.1016/j.dyepig.2008.03.003

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 journal › Article › peer-review

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 language	English (US)
Pages (from-to)	242-246
Number of pages	5
Journal	Dyes and Pigments
Volume	79
Issue number	3
DOIs	https://doi.org/10.1016/j.dyepig.2008.03.003
State	Published - Dec 2008
Externally published	Yes

Keywords

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

ASJC Scopus subject areas

General Chemical Engineering
Process Chemistry and Technology

Access to Document

10.1016/j.dyepig.2008.03.003

Cite this

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title = "A novel synthetic route to thiacyanine dyes containing a perfluorinated polymethine chain",

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.",

keywords = "2-Trifluorovinylbenzothiazole, Fluoride ion, Perfluorinated polymethine chain, Thiacarbocyanine dye, α,β-Difluorosubstituted dyes",

author = "Yagupolskii, {L. M.} and Kondratenko, {N. V.} and Chernega, {O. I.} and Chernega, {A. N.} and Buth, {S. A.} and Yagupolskii, {Yu L.}",

year = "2008",

month = dec,

doi = "10.1016/j.dyepig.2008.03.003",

language = "English (US)",

volume = "79",

pages = "242--246",

journal = "Dyes and Pigments",

issn = "0143-7208",

publisher = "Elsevier BV",

number = "3",

}

TY - JOUR

T1 - A novel synthetic route to thiacyanine dyes containing a perfluorinated polymethine chain

AU - Yagupolskii, L. M.

AU - Kondratenko, N. V.

AU - Chernega, O. I.

AU - Chernega, A. N.

AU - Buth, S. A.

AU - Yagupolskii, Yu L.

PY - 2008/12

Y1 - 2008/12

N2 - 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.

AB - 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.

KW - 2-Trifluorovinylbenzothiazole

KW - Fluoride ion

KW - Perfluorinated polymethine chain

KW - Thiacarbocyanine dye

KW - α,β-Difluorosubstituted dyes

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U2 - 10.1016/j.dyepig.2008.03.003

DO - 10.1016/j.dyepig.2008.03.003

M3 - Article

AN - SCOPUS:44749087514

SN - 0143-7208

VL - 79

SP - 242

EP - 246

JO - Dyes and Pigments

JF - Dyes and Pigments

IS - 3

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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