Excited-State Intramolecular Proton Transfer Reaction of 3-Hydroxyflavone

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• 作者：Yanxue Jiang ; Yajing Peng
• 关键词：TD ; DFT ; Infrared spectra ; Frontier molecular orbitals ; Excited ; state intramolecular proton transfer ; Potential energy curves
• 刊名：Journal of Cluster Science
• 出版年：2015
• 出版时间：November 2015
• 年：2015
• 卷：26
• 期：6
• 页码：1983-1992
• 全文大小：1,490 KB
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• 作者单位：Yanxue Jiang (1)
  Yajing Peng (1) (2) (3)
  
  1. Academy of Mathematics and Physics, Department of Physics, Bohai University, Jinzhou, 121013, China
  2. State Key Lab of Molecular Reaction Dynamics, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, 116023, China
  3. State Key Laboratory of Explosion Science and Technology, Beijing Institute of Technology, Beijing, 100081, China
  
• 刊物类别：Chemistry and Materials Science
• 刊物主题：Chemistry
  Catalysis
  Inorganic Chemistry
  Physical Chemistry
  
• 出版者：Springer Netherlands
• ISSN：1572-8862

文摘

The excited-state intramolecular proton transfer (ESIPT) reaction of 3-hydroxyflavone (3-HF) in methylcyclohexane solvent has been investigated by using the DFT and TD-DFT methods. The geometric structure, IR vibrational spectra, frontier molecular orbitals, natural bond orbital, and potential energy curves in the ground state (S₀) and first excited state (S₁) are analyzed to reveal the mechanism of proton transfer. The results demonstrate that there are enol- and keto- two isomers for 3-HF in the S₁, which is accorded with the experimental double fluorescence bands. The 3-HF-enol can be isomerized into 3-HF-keto via ESIPT. The mechanism of proton transfer is attributed to the strengthening of hydrogen bond originated from intramolecular charge transfer. The potential energy curves in the S₀ and S₁ states also illuminate the tautomerism mechanism between 3-HF-enol and 3-HF-keto, and the ground-state 3-HF-keto might not exist long and is isomerized mostly into the 3-HF-enol due to its high energy or instability. This is the reason that only one absorption peak is observed for 3-HF in experiment. Keywords TD-DFT Infrared spectra Frontier molecular orbitals Excited-state intramolecular proton transfer Potential energy curves