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Open Chemistry

formerly Central European Journal of Chemistry

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IMPACT FACTOR 2016 (Open Chemistry): 1.027
IMPACT FACTOR 2016 (Central European Journal of Chemistry): 1.460

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2391-5420
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Volume 8, Issue 2 (Apr 2010)

Issues

Structure and spectal properties of cinnamoyl pyrones and their vinylogs

Dmytro Tykhanov
  • Department of Physical Organic Chemistry, Institute of Chemistry at Kharkov National University, Kharkov, 61077, Ukraine
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/ Irina Serikova
  • Danilevskii Institute of Endocrine Pathology Problems, Ukrainian Academy of Medical Sciences, Kharkov, 61002, Ukraine
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/ Fedor Yaremenko
  • Danilevskii Institute of Endocrine Pathology Problems, Ukrainian Academy of Medical Sciences, Kharkov, 61002, Ukraine
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/ Alexander Roshal
  • Department of Physical Organic Chemistry, Institute of Chemistry at Kharkov National University, Kharkov, 61077, Ukraine
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Published Online: 2010-03-23 | DOI: https://doi.org/10.2478/s11532-009-0138-4

Abstract

The 1H-NMR and quantum chemical analysis of the stability of tautomers of cinnamoyl pyrone derivatives and vinylogs has been studied. The relationship between the structure of the most stable tautomer and its spectral properties has been investigated. It has been determined that the tautomer of highest stability (88–100 molar %) has an α-pyrone structure and exhibits a trans-conformation in the cinnamoyl fragment. An intense fluorescence of dyes has been observed in non-polar solvents with cinnamoyl fragments having electron-donating substituents or several double bonds in the polymethine chain. A gradient in solvent polarity resulted in fluorescence quenching which permits the use of the dyes as intensometric fluorometric probes for medium polarity examination.

Keywords: Cinnamoyl pyrones; Fluorescent dyes; Quantum chemical calculations; Absorption and fluorescence spectral properties; Fluorescent probes

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About the article

Published Online: 2010-03-23

Published in Print: 2010-04-01


Citation Information: Open Chemistry, ISSN (Online) 2391-5420, DOI: https://doi.org/10.2478/s11532-009-0138-4.

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