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Unusually slow proton transfer dynamics of a 3-hydroxychromone dye in protic solvents.
Photochem Photobiol Sci. 2009 Nov; 8(11):1583-9.PP

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.

Authors+Show Affiliations

Laboratoire de Biophotonique et Pharmacologie, UMR 7213 du CNRS, Université de Strasbourg, Faculté de Pharmacie, 74 route du Rhin, 67401, Illkirch, France. bkgcranjandas@rediffmail.comNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

19862417

Citation

Das, Ranjan, et al. "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, vol. 8, no. 11, 2009, pp. 1583-9.
Das R, Klymchenko AS, Duportail G, et al. Unusually slow proton transfer dynamics of a 3-hydroxychromone dye in protic solvents. Photochem Photobiol Sci. 2009;8(11):1583-9.
Das, R., Klymchenko, A. S., Duportail, G., & Mély, Y. (2009). 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, 8(11), 1583-9. https://doi.org/10.1039/b906710h
Das R, et al. Unusually Slow Proton Transfer Dynamics of a 3-hydroxychromone Dye in Protic Solvents. Photochem Photobiol Sci. 2009;8(11):1583-9. PubMed PMID: 19862417.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Unusually slow proton transfer dynamics of a 3-hydroxychromone dye in protic solvents. AU - Das,Ranjan, AU - Klymchenko,Andrey S, AU - Duportail,Guy, AU - Mély,Yves, Y1 - 2009/09/21/ PY - 2009/10/29/entrez PY - 2009/10/29/pubmed PY - 2010/2/24/medline SP - 1583 EP - 9 JF - Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology JO - Photochem Photobiol Sci VL - 8 IS - 11 N2 - 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. SN - 1474-9092 UR - https://www.unboundmedicine.com/medline/citation/19862417/Unusually_slow_proton_transfer_dynamics_of_a_3_hydroxychromone_dye_in_protic_solvents_ L2 - https://doi.org/10.1039/b906710h DB - PRIME DP - Unbound Medicine ER -