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- Title
Investigation of excited-state intramolecular proton transfer coupled charge transfer reaction of paeonol.
- Authors
Hu, Shanshan; Liu, Kun; Li, Yuanzuo; Ding, Qianqian; Peng, Wei; Chen, Maodu
- Abstract
An excited-state intramolecular proton transfer (ESIPT) coupled charge transfer reaction of paeonol was investigated both experimentally and theoretically. The ESIPT reaction of paeonol was predicted based on the large Stokes shift, which is observed in steady-state absorption and fluorescence spectra in an ethanol solution. The steady-state spectra in some solutions, such as methanol, ethanol, propanol, dichloromethane, and n-hexane, illustrate that the ESIPT reaction of paeonol has no dependence on the solvent properties. Therefore, the excited-state intermolecular proton transfer cannot be generated in protic solvents. Using the density functional theory and time-dependent density functional theory methods, we make a subsequent theoretical calculation that indicates that the ESIPT reaction of paeonol occurs through the intramolecular hydrogen bond O−H···O=C. The excited-state potential energy curve of paeonol indicates that the ESIPT reaction is a barrierless process, and the fluorescence emission of paeonol at 493 nm in the ethanol solution was assigned to the keto isomer fluorescence. Additionally, we also found an intramolecular charge transfer in the excited state by analysing the frontier molecular orbitals of paeonol.
- Subjects
INTRAMOLECULAR proton transfer reactions; DICHLOROMETHANE; ACETOPHENONE; DENSITY functional theory; EXCITED state chemistry; CHARGE transfer; FLUORESCENCE spectroscopy
- Publication
Canadian Journal of Chemistry, 2014, Vol 92, Issue 4, p274
- ISSN
0008-4042
- Publication type
Article
- DOI
10.1139/cjc-2013-0286