Structure and spectal properties of cinnamoyl pyrones and their vinylogs |
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Authors: | Dmytro A Tykhanov Irina I Serikova Fedor G Yaremenko Alexander D Roshal |
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Institution: | (1) Pyatigorsk State Pharmaceutical Academy, Pyatigorsk, Russia;(2) North-Ossetian State University, Vladikavkaz, North Ossetia, Russia; |
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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.
![MediaObjects/11532_2009_138_Fig1_HTML.jpg](/content/46616603514R78W2/MediaObjects/11532_2009_138_Fig1_HTML.jpg) |
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