Issue 13, 2011

Solvent effect on the excited-state proton transfer of 7-hydroxyquinoline along a hydrogen-bonded ethanol dimer

Abstract

We have studied the solvent effect on structures and potential energy surfaces along proton transfer in the ground and the excited states of 7-hydroxyquinoline interacting with an ethanol dimer using ab initio calculations. The proton transfer is forbidden in the ground state not only in vacuum but also in solvents of n-heptane, ethanol, and dimethyl sulfoxide. In the excited state, although the proton transfer is forbidden in vacuum, it is possible in solvent due to its greatly reduced barrier (∼10 kcal mol−1) and highly stabilized product. It has also been found from the calculations that the proton-transfer barrier in the excited state decreases as the dielectric constant of a solvent increases. Our calculations are consistent with experimental results that the proton transfer does not take place in the ground state and that the excited-state proton-transfer rate increases as the solvent polarity increases. Our calculated absorption and emission properties are in excellent agreement with experimental results. Projection factors (reflecting geometrical change from the ground state to the excited state) and reorganization energies for several low frequency vibrations in connection with the excited-state proton transfer are discussed as well.

Graphical abstract: Solvent effect on the excited-state proton transfer of 7-hydroxyquinoline along a hydrogen-bonded ethanol dimer

Supplementary files

Article information

Article type
Paper
Submitted
01 Nov 2010
Accepted
02 Feb 2011
First published
28 Feb 2011

Phys. Chem. Chem. Phys., 2011,13, 6332-6339

Solvent effect on the excited-state proton transfer of 7-hydroxyquinoline along a hydrogen-bonded ethanol dimer

B. Kang, K. C. Ko, S. Park, D. Jang and J. Y. Lee, Phys. Chem. Chem. Phys., 2011, 13, 6332 DOI: 10.1039/C0CP02347G

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