Title: Theoretical Investigation of Excited-State Intramolecular Proton Transfer Mechanism of Flavonoid Derivatives
Abstract: Hydrogen-Bonding Research in Photochemistry, Photobiology, and Optoelectronic Materials, pp. 179-213 (2019) No AccessChapter 8: Theoretical Investigation of Excited-State Intramolecular Proton Transfer Mechanism of Flavonoid DerivativesZhe Tang, Yi Wang, and Ningjiu ZhaoZhe TangSchool of Biological Engineering, Dalian Polytechnic University, Dalian 116034, ChinaState Key Laboratory of Molecular Reaction Dynamics, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, China, Yi WangSchool of Biological Engineering, Dalian Polytechnic University, Dalian 116034, China, and Ningjiu ZhaoState Key Laboratory of Molecular Reaction Dynamics, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, Chinahttps://doi.org/10.1142/9781786346087_0008Cited by:2 PreviousNext AboutSectionsPDF/EPUB ToolsAdd to favoritesDownload CitationsTrack CitationsRecommend to Library ShareShare onFacebookTwitterLinked InRedditEmail Abstract: The flavonoid derivatives of 4′-dimethylaminoflavonol (DMAF) in acetonitrile solvent and 3,7-dihydroxy-4-oxo-2-phenyl-4H-chromene-8-carbaldehyde (2a) in methylcyclohexane solvent have been investigated on the excited-state intramolecular proton transfer (ESIPT) based on the time-dependent density functional theory (TDDFT) method. The calculated absorption and fluorescence spectra agree well with the experimental results. The analyses of bond distance, bond angle, the molecular electrostatic potential surface and the infrared vibrational spectra show that intramolecular hydrogen bonds were formed in the S0 state, and upon excitation, the intramolecular hydrogen bonds were strengthened in the S1 state, which can facilitate the proton-transfer (PT) process. The constructed potential-energy curves/surfaces (PES) on the S1 and S0 states can be used to demonstrate the PT process. In terms of DMAF with one hydrogen bond, our calculations suggest that intramolecular hydrogen bonds can boost intramolecular PT in the twisted intramolecular charge-transfer (TICT) state. For the flavonoid derivative bearing two hydrogen bonds, i.e., 2a, however, the TICT state has little impact on 2a. Instead, three PT types in the excited state (ES) occur. By analyzing the PES, the preferred pathway was also determined. Our work not only gives a detailed PT process in the ES but also provides theoretical significance for further study of flavonoid derivatives. Keywords: Flavonoid derivativesTDDFTESIPTTICTPES FiguresReferencesRelatedDetailsCited By 2Modern Theoretical Approaches to Modeling the Excited-State Intramolecular Proton Transfer: An OverviewJoanna Jankowska and Andrzej L. Sobolewski25 August 2021 | Molecules, Vol. 26, No. 17Molecular design of amino-type hydrogen-bonding molecules for excited-state intramolecular proton transfer (ESIPT)-based fluorescent probe using the TD-DFT approachNarissa Kanlayakan and Nawee Kungwan1 January 2021 | New Journal of Chemistry, Vol. 45, No. 28 Hydrogen-Bonding Research in Photochemistry, Photobiology, and Optoelectronic MaterialsMetrics History KeywordsFlavonoid derivativesTDDFTESIPTTICTPESPDF download
Publication Year: 2019
Publication Date: 2019-03-01
Language: en
Type: book-chapter
Indexed In: ['crossref']
Access and Citation
Cited By Count: 2
AI Researcher Chatbot
Get quick answers to your questions about the article from our AI researcher chatbot