Dual fluorescence of 1-hydroxy-substituted Nile Red dye in the red and near-infrared spectral range: Excited-state proton transfer along intramolecular hydrogen bond

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Abstract

Photophysical properties of 1-hydroxy-substituted Nile Red dye proved to be entirely different from those of its 2-hydroxy isomer. Strong hydrogen bonding between the 1-HO-moiety and the heterocyclic nitrogen of the molecule made deprotonation with bases very difficult but facilitated photoinduced tautomerization via intramolecular proton transfer. Dual fluorescence was found in all solvents and the relative intensity of the two bands markedly changed with the polarity as well as hydrogen bond donating power of the medium. The quantum yield for both the normal fluorescence and the tautomer emission went through a maximum as a function of the ET(30) solvent polarity parameter with highest values obtained in dichloromethane.

Original languageEnglish
Pages (from-to)92-97
Number of pages6
JournalChemical Physics Letters
Volume440
Issue number1-3
DOIs
Publication statusPublished - May 25 2007

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Proton transfer
Excited states
polarity
Hydrogen bonds
Coloring Agents
dyes
Fluorescence
hydrogen bonds
Infrared radiation
fluorescence
Deprotonation
protons
Methylene Chloride
tautomers
Quantum yield
Isomers
excitation
Nitrogen
isomers
nitrogen

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Spectroscopy
  • Atomic and Molecular Physics, and Optics
  • Surfaces and Interfaces
  • Condensed Matter Physics

Cite this

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title = "Dual fluorescence of 1-hydroxy-substituted Nile Red dye in the red and near-infrared spectral range: Excited-state proton transfer along intramolecular hydrogen bond",
abstract = "Photophysical properties of 1-hydroxy-substituted Nile Red dye proved to be entirely different from those of its 2-hydroxy isomer. Strong hydrogen bonding between the 1-HO-moiety and the heterocyclic nitrogen of the molecule made deprotonation with bases very difficult but facilitated photoinduced tautomerization via intramolecular proton transfer. Dual fluorescence was found in all solvents and the relative intensity of the two bands markedly changed with the polarity as well as hydrogen bond donating power of the medium. The quantum yield for both the normal fluorescence and the tautomer emission went through a maximum as a function of the ET(30) solvent polarity parameter with highest values obtained in dichloromethane.",
author = "Z. Miskolczy and L. Bicz{\'o}k and I. Jablonkai",
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T1 - Dual fluorescence of 1-hydroxy-substituted Nile Red dye in the red and near-infrared spectral range

T2 - Excited-state proton transfer along intramolecular hydrogen bond

AU - Miskolczy, Z.

AU - Biczók, L.

AU - Jablonkai, I.

PY - 2007/5/25

Y1 - 2007/5/25

N2 - Photophysical properties of 1-hydroxy-substituted Nile Red dye proved to be entirely different from those of its 2-hydroxy isomer. Strong hydrogen bonding between the 1-HO-moiety and the heterocyclic nitrogen of the molecule made deprotonation with bases very difficult but facilitated photoinduced tautomerization via intramolecular proton transfer. Dual fluorescence was found in all solvents and the relative intensity of the two bands markedly changed with the polarity as well as hydrogen bond donating power of the medium. The quantum yield for both the normal fluorescence and the tautomer emission went through a maximum as a function of the ET(30) solvent polarity parameter with highest values obtained in dichloromethane.

AB - Photophysical properties of 1-hydroxy-substituted Nile Red dye proved to be entirely different from those of its 2-hydroxy isomer. Strong hydrogen bonding between the 1-HO-moiety and the heterocyclic nitrogen of the molecule made deprotonation with bases very difficult but facilitated photoinduced tautomerization via intramolecular proton transfer. Dual fluorescence was found in all solvents and the relative intensity of the two bands markedly changed with the polarity as well as hydrogen bond donating power of the medium. The quantum yield for both the normal fluorescence and the tautomer emission went through a maximum as a function of the ET(30) solvent polarity parameter with highest values obtained in dichloromethane.

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