Russian Chemical Bulletin

, Volume 54, Issue 12, pp 2820–2830 | Cite as

Synthesis and spectral properties of malononitrile-based merocyanine dyes

  • A. V. Kulinich
  • N. A. Derevyanko
  • A. A. Ishchenko


Di-, tetra-, and hexamethine merocyanines derived from malononitrile and heterocycles with moderate (dyes 1–6), strong (7–9), and weak (10 and 11) electron-releasing ability were synthesized. The electronic structures of merocyanines 10 and 11 are similar to the neutral polyene state, whereas those of 7–9 are similar to the ideal polymethine state. These tendencies become more pronounced with increasing length of the polymethine chain. The merocyanines derived from heterocyclic residues with weak or moderate electron-releasing ability exhibit a positive solvatochromism, whereas those with strong electron-releasing ability show a negative solvatochromism. An increase in the polarity of the solvent makes the former compounds more similar to polymethines, whereas the latter become more similar to polyenes bearing opposite charges on the end groups. The nature of the factors (nonspecific solvation, specific nucleophilic and electrophilic solvation, and vibronic interactions) responsible for the observed characteristic features was analyzed.

Key words

merocyanines polyene and polymethine states positive and negative solvato-chromism vibronic and intermolecular interactions 


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Copyright information

© Springer Science+Business Media, Inc. 2005

Authors and Affiliations

  • A. V. Kulinich
    • 1
  • N. A. Derevyanko
    • 2
  • A. A. Ishchenko
    • 2
  1. 1.Taras Shevchenko Kiev State UniversityKievUkraine
  2. 2.Institute of Organic ChemistryNational Academy of Sciences of UkraineKievUkraine

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