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Russian Chemical Bulletin

, Volume 58, Issue 4, pp 828–837 | Cite as

Deeply colored anionic polymethine dyes derived from bis(2,2,3,3,4,4,5,5-octafluoropentyl) 9 H-fluorene-2,7-disulfonate

  • I. V. Kurdyukova
  • N. A. Derevyanko
  • A. A. Ishchenko
  • D. D. Mysyk
Full Articles

Abstract

Anionic symmetric polymethine dyes have been synthesized based on bis(2,2,3,3,4,4,5,5-octafluoropentyl) 9H-fluorene-2,7-disulfonate, which exhibit intensive absorption in the near IR region of the spectrum: pentamethine with an open polymethine chain (⋉max = 790 nm) and nonamethine with six- and five-membered saturated rings at δ-positions of the chain (@#@max = 1044 and 1086 nm, respectively). To make comparisons, anionic dyes with analogous structure of the polymethine chain, viz., 1,3-dimethylbarbituric and 1,3-diethylthiobarbituric acid derivatives, have been also synthesized. Quantum chemical analysis of the electron structure of the dyes has been performed. Their solvatochromism in polar solvents depends weakly on electrophilicity and nucleophilicity of the medium and is primarily determined by universal interactions. This is the reason that they, in contrast to cationic dyes, retain a high selectivity of absorption (sharp absorption bands) and universal contour of electronic bands in strong polar solvents even with the long polymethine chain. Special solvatochromic effects of the anionic dyes in weakly polar media have been revealed and interpreted. The role of a counterion in these effects has been analyzed.

fluorene anionic dyes intimate ion pairs solvatochromism absorption spectra organofluorine compounds 

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Copyright information

© Springer Science+Business Media, Inc.  2009

Authors and Affiliations

  • I. V. Kurdyukova
    • 1
  • N. A. Derevyanko
    • 1
  • A. A. Ishchenko
    • 1
  • D. D. Mysyk
    • 2
  1. 1.Institute of Organic ChemistryNational Academy of Sciences of UkraineKievUkraine
  2. 2.Donetsk National Technical UniversityDonetskUkraine

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