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Environment-sensitive quinolone demonstrating long-lived fluorescence and unusually slow excited-state intramolecular proton transfer kinetics
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SYSNO ASEP 0471842 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Environment-sensitive quinolone demonstrating long-lived fluorescence and unusually slow excited-state intramolecular proton transfer kinetics Author(s) Zamotaiev, O. M. (UA)
Shvadchak, Volodymyr (UOCHB-X) RID, ORCID
Sych, T. P. (FR)
Melnychuk, N. A. (UA)
Yushchenko, Dmytro A. (UOCHB-X) ORCID, RID
Mely, Y. (FR)
Pivovarenko, V. G. (UA)Article number 034004 Source Title Methods and Applications in Fluorescence. - : Institute of Physics Publishing - ISSN 2050-6120
Roč. 4, č. 3 (2016)Number of pages 10 s. Language eng - English Country GB - United Kingdom Keywords quinolone ; fluorescent probes ; local polarity ; hydration ; excited-state intramolecular proton transfer ; kinetics Subject RIV CC - Organic Chemistry Institutional support UOCHB-X - RVO:61388963 UT WOS 000396085000001 DOI 10.1088/2050-6120/4/3/034004 Annotation A new small fluorescent dye based on 3-hydroxybenzo[g]quinolone, a benzo-analogue of Pseudomonas quinolone signal species, has been synthesized. The dye demonstrates interesting optical properties, with absorption in the visible region, two band emission due to an excited-state intramolecular proton transfer (ESIPT) reaction and high fluorescence quantum yield in both protic and aprotic media. Time-resolved fluorescence spectroscopy shows that the ESIPT reaction time is unusually long (up to 8 ns), indicating that both forward and backward ESIPT reactions are very slow in comparison to other 3-hydroxyquinolones. In spite of these slow rate constants, the ESIPT reaction was found to show a reversible character as a result of the very long lifetimes of both N* and T* forms (up to 16 ns). The ESIPT reaction rate is mainly controlled by the hydrogen bond donor ability in protic solvents and the polarity in aprotic solvents. Using large unilamellar vesicles and giant unilamellar vesicles of different lipid compositions, the probe was shown to preferentially label liquid disordered phases. Workplace Institute of Organic Chemistry and Biochemistry Contact asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Viktorie Chládková, Tel.: 232 002 434 Year of Publishing 2017
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