Investigation of ESIPT in a panel of chromophores presenting N-H⋯N intramolecular hydrogen bonds

Pierre O. Hubin, Adèle D. Laurent, Daniel P. Vercauteren, Denis Jacquemin

Research output: Contribution to journalArticle

Abstract

Thermodynamic and kinetic aspects of excited state intramolecular proton transfer (ESIPT) are investigated in 11 chromophores harboring an intramolecular N-H⋯N hydrogen bond [pyridyl pyrazole, pyridyl pyrrole, azaindole, pyridyl indole, pyrroloquinoline, and an analogue of the Blue Fluorescent Protein (BFP) chromophore] with the help of quantum mechanical calculations. For pyridyl pyrazoles, simulated spectra are used to help the interpretation of experimental ones and the effects of several substituents are investigated. Then it is shown that Time-Dependent Density Functional Theory fails to satisfactorily describe the energetic aspects of ESIPT for the BFP chromophore analogue. Equation-of-Motion Coupled Cluster theory is thus used to reach accurate insights for this challenging case. This journal is

Original languageEnglish
Pages (from-to)25288-25295
Number of pages8
JournalPhysical Chemistry Chemical Physics
Volume16
Issue number46
Early online date30 Sep 2014
DOIs
Publication statusPublished - 14 Dec 2014

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Proton transfer
Chromophores
Excited states
chromophores
Hydrogen bonds
hydrogen bonds
protons
Pyrazoles
analogs
excitation
proteins
Pyrroles
indoles
pyrroles
Equations of motion
Density functional theory
equations of motion
Proteins
Thermodynamics
density functional theory

Cite this

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abstract = "Thermodynamic and kinetic aspects of excited state intramolecular proton transfer (ESIPT) are investigated in 11 chromophores harboring an intramolecular N-H⋯N hydrogen bond [pyridyl pyrazole, pyridyl pyrrole, azaindole, pyridyl indole, pyrroloquinoline, and an analogue of the Blue Fluorescent Protein (BFP) chromophore] with the help of quantum mechanical calculations. For pyridyl pyrazoles, simulated spectra are used to help the interpretation of experimental ones and the effects of several substituents are investigated. Then it is shown that Time-Dependent Density Functional Theory fails to satisfactorily describe the energetic aspects of ESIPT for the BFP chromophore analogue. Equation-of-Motion Coupled Cluster theory is thus used to reach accurate insights for this challenging case. This journal is",
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Investigation of ESIPT in a panel of chromophores presenting N-H⋯N intramolecular hydrogen bonds. / Hubin, Pierre O.; Laurent, Adèle D.; Vercauteren, Daniel P.; Jacquemin, Denis.

In: Physical Chemistry Chemical Physics, Vol. 16, No. 46, 14.12.2014, p. 25288-25295.

Research output: Contribution to journalArticle

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