Unusually slow proton transfer dynamics of a 3-hydroxychromone dye in protic solvents

Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology
Ranjan DasY Mély

Abstract

The photophysics of a 3-hydroxychromone dye, 2-(2-furyl)-3-hydroxychromone (FHC) was explored in different types of protic solvents by steady-state and time-resolved fluorescence spectroscopy. FHC exhibits a dual emission, attributable to the excited normal (N*) and tautomer (T*) forms resulting from an excited state intramolecular proton transfer (ESIPT) reaction (N*-->T*). The ESIPT rate decreases with an increase in the hydrogen-bond donating ability of protic solvents. The proton-transfer dynamics is found to be unusually slow ( approximately 10(3) times slower than 3-hydroxyflavone) in strong hydrogen-bond donating solvents like methanol, trifluoroethanol or formamide, where it occurs on a time scale of approximately 100-260 picoseconds. This slow dynamics is likely to be related to the intermolecular solvent-solute H-bonding interactions that compete with the intramolecular H-bond in FHC required for the ESIPT reaction. These data provide a physical background for recent applications of this dye as a fluorescence probe of the microenvironment in biomolecules.

References

Oct 10, 2002·Journal of the American Chemical Society·Andrey S Klymchenko, Alexander P Demchenko
Nov 26, 2002·Chemistry & Biology·Andrey S KlymchenkoAlexander P Demchenko
Mar 1, 2003·Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy·Andrey S KlymchenkoAlexander P Demchenko
Mar 2, 2005·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Fabiano Severo RodembuschValter Stefani
Jun 1, 2005·Biochimica Et Biophysica Acta·Vasyl V ShynkarYves Mély
Jan 4, 2007·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Mateus Borba CardosoValter Stefani
Jan 30, 2007·Journal of the American Chemical Society·Vasyl V ShynkarYves Mely
Oct 4, 2007·The Journal of Physical Chemistry. a·Dmytro A YushchenkoYves Mély
Aug 30, 2008·The Journal of Physical Chemistry. B·Ranjan DasYves Mély
Sep 5, 2008·The Journal of Physical Chemistry. B·Andrey S KlymchenkoYves Mély

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Citations

Mar 27, 2012·Annual Review of Biochemistry·Liguo Wang
Nov 12, 2015·Journal of Photochemistry and Photobiology. B, Biology·Asli CapanTuran Ozturk
Feb 17, 2017·Physical Chemistry Chemical Physics : PCCP·Aurelie PerveauxDavid Lauvergnat
Mar 7, 2018·Physical Chemistry Chemical Physics : PCCP·Anastasia Ioanna SkilitsiJérémie Léonard
May 25, 2010·Journal of the American Chemical Society·Dmytro A YushchenkoThomas M Jovin
Dec 23, 2010·Bioconjugate Chemistry·Oleksandr M ZamotaievYves Mély
Mar 8, 2012·The Journal of Physical Chemistry. a·Vasyl G PivovarenkoYves Mély
Nov 10, 2018·The Journal of Physical Chemistry. a·Quinton J MeisnerLei Zhu
Nov 17, 2012·Bioconjugate Chemistry·Aleksandr V StrizhakYves Mély

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