Issue 124, 2015

10-Hydroxybenzo[h]quinoline: switching between single- and double-well proton transfer through structural modifications

Abstract

Proton transfer in 10-hydroxybenzo[h]quinoline (HBQ) and structurally modified compounds was investigated experimentally (steady state UV-Vis absorption and emission spectroscopy, NMR and advanced chemometric techniques) and theoretically (DFT and TD-DFT M06-2X/TZVP calculations) in the ground and excited singlet state. We observed that the incorporation of electron acceptor substituents on position 7 of the HBQ backbone led to appearance of a keto tautomer in ground state and changes in the excited state potential energy surface. Both processes were strongly solvent dependent. In the ground state the equilibrium could be driven from the enol to the keto form by change of solvent. The theoretical calculations explain the substitution-determined transition from a single- to a double-well proton transfer mechanism.

Graphical abstract: 10-Hydroxybenzo[h]quinoline: switching between single- and double-well proton transfer through structural modifications

Supplementary files

Article information

Article type
Paper
Submitted
28 Sep 2015
Accepted
18 Nov 2015
First published
23 Nov 2015
This article is Open Access
Creative Commons BY license

RSC Adv., 2015,5, 102495-102507

10-Hydroxybenzo[h]quinoline: switching between single- and double-well proton transfer through structural modifications

S. Hristova, G. Dobrikov, F. S. Kamounah, S. Kawauchi, P. E. Hansen, V. Deneva, D. Nedeltcheva and L. Antonov, RSC Adv., 2015, 5, 102495 DOI: 10.1039/C5RA20057A

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