Details

Autor(en) / Beteiligte

• Hristova, S
• Dobrikov, G
• Kamounah, F. S
• Kawauchi, S
• Hansen, P. E
• Deneva, V
• Nedeltcheva, D
• Antonov, L

Titel

10-Hydroxybenzo[h]quinoline: switching between single- and double-well proton transfer through structural modificationsThis paper is dedicated to Prof. Nikolai Tyutyulkov (1927-2015), founder of quantum chemistry in Bulgaria, memorable teacher and a good person.Electronic supplementary information (ESI) available. See DOI: 10.1039/c5ra20057a

Erscheinungsjahr

2015-11

Link zum Volltext

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• 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. Proton transfer in HBQ and modified compounds was investigated experimentally (steady state absorption and emission spectroscopy, NMR and chemometrics) and theoretically (DFT and TD-DFT M06-2X/TZVP calculations) in ground and excited singlet state.