Experimental and Theoretical Investigation on Excited State Intramolecular Proton Transfer Coupled Charge Transfer Reaction of Baicalein

2014 ◽  
Vol 27 (1) ◽  
pp. 51-56
Author(s):  
Shan-shan Hu ◽  
Kun Liu ◽  
Qian-qian Ding ◽  
Wei Peng ◽  
Mao-du Chen
Keyword(s):  
Excited State ◽  
Charge Transfer ◽  
Proton Transfer ◽  
Theoretical Investigation ◽  
Transfer Reaction ◽  
Intramolecular Proton Transfer ◽  
Charge Transfer Reaction

Investigation of excited-state intramolecular proton transfer coupled charge transfer reaction of paeonol

2014 ◽  
Vol 92 (4) ◽  
pp. 274-278 ◽  
Author(s):  
Shanshan Hu ◽  
Kun Liu ◽  
Yuanzuo Li ◽  
Qianqian Ding ◽  
Wei Peng ◽  
...  
Keyword(s):  
Density Functional Theory ◽  
Excited State ◽  
Charge Transfer ◽  
Proton Transfer ◽  
Density Functional ◽  
Transfer Reaction ◽  
Intramolecular Proton Transfer ◽  
Ethanol Solution ◽  
Charge Transfer Reaction ◽  
Functional Theory

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.

Experimental and theoretical investigation of long-wavelength fluorescence emission in push–pull benzazoles: intramolecular proton transfer or charge transfer in the excited state?

2019 ◽  
Vol 21 (8) ◽  
pp. 4408-4420 ◽  
Author(s):  
Guilherme Wiethaus ◽  
Josene Maria Toldo ◽  
Fabiano da Silveira Santos ◽  
Rodrigo da Costa Duarte ◽  
Paulo Fernando Bruno Gonçalves ◽  
...  
Keyword(s):  
Excited State ◽  
Charge Transfer ◽  
Proton Transfer ◽  
Theoretical Investigation ◽  
Fluorescence Emission ◽  
Intramolecular Proton Transfer ◽  
Long Wavelength

ESIPT is disfavoured and charge-transfer emission, prior to ESIPT, seems to be responsible for long-emission wavelengths.

scholarly journals Ingenious modification of molecular structure effectively regulates excited-state intramolecular proton and charge transfer: a theoretical study based on 3-hydroxyflavone

RSC Advances ◽  
2018 ◽  
Vol 8 (52) ◽  
pp. 29589-29597 ◽  
Author(s):  
Jianhui Han ◽  
Xiaochun Liu ◽  
Chaofan Sun ◽  
You Li ◽  
Hang Yin ◽  
...  
Keyword(s):  
Molecular Structure ◽  
Excited State ◽  
Charge Transfer ◽  
Proton Transfer ◽  
Theoretical Study ◽  
Intramolecular Charge Transfer ◽  
Intramolecular Proton Transfer ◽  
Great Promise ◽  
Fluorescence Sensing

Harnessing ingenious modification of molecular structure to regulate excited-state intramolecular proton transfer (ESIPT) and intramolecular charge transfer (ICT) characteristics holds great promise in fluorescence sensing and imaging.

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