Diphenyloxazole substituted 3-hydroxychromones - perspective luminophores for ratiometric studies.
In: Ukrainica Bioorganica Acta, Jg. 6 (2008-12-01), Heft 2, S. 38-45
Online
academicJournal
Zugriff:
A new heterocyclic derivatives of 3-hydroxychromone with the 2,5-diphenyloxazole moiety in position 2 were synthesized. It was shown that the composition of these two fragments lead to one of the most effective fluorescent compounds in the 3-hydroxychromone family, preserving anomalous spectral properties caused by a proton phototransfer reaction. Based on computation results, both title compounds were shown to be systems with a reverse charge transfer preserving their ability to form a phototautomer in the excited state. It was stated that an annelated benzene ring leads to decrease of the charge transfer intensity during the excitation, which causes lower solvatofluorochromism as well as lower sensitivity of the ratiometric response on the solvent polarity changes. Spectral and fluorescent properties, as well as solvatofluorochromism and influence of the solvent polarity on the excited state intramolecular proton phototransfer process were investigated for the synthesized compounds in a series of 9 different solvents. Both derivatives are characterized by the absorption and fluorescence maxima close to the ones for the unsubstituted 3-hydroxyflavone, sometimes with slightly higher quantum yields of fluorescence. Both absorption and tautomer emission maxima are almost insensitive to the solvent polarity, while the position of the normal form fluorescence exhibits a significant bathochromic shift with the increase of the solvent polarity. A possibility was shown to use the title compounds as ratiometric probes of the medium polarity. [ABSTRACT FROM AUTHOR]
Titel: |
Diphenyloxazole substituted 3-hydroxychromones - perspective luminophores for ratiometric studies.
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Autor/in / Beteiligte Person: | Svechkarev, D. A. ; Karpushina, G. V. ; Doroshenko, A. O. |
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Zeitschrift: | Ukrainica Bioorganica Acta, Jg. 6 (2008-12-01), Heft 2, S. 38-45 |
Veröffentlichung: | 2008 |
Medientyp: | academicJournal |
ISSN: | 1814-9758 (print) |
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