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Chin. Phys. B, 2020, Vol. 29(5): 058202    DOI: 10.1088/1674-1056/ab7ea1

Relationship between ESIPT properties and antioxidant activities of 5-hydroxyflavone derivates

Chaofan Sun(孙朝范), Bifa Cao(曹必发), Hang Yin(尹航), Ying Shi(石英)
Institute of Atomic and Molecular Physics, Jilin University, Changchun 130012, China
Abstract  It is of great significance to study the relationship between the excited state intramolecular proton transfer (ESIPT) properties and antioxidant activities of compounds in the field of life sciences. In this work, two novel compounds 5HF-OMe and 5HF-NH2 are designed through introducing a methoxy- and amino-group into the structure of 5-hydroxyflavone (5HF) respectively. The relationship between the ESIPT reaction and antioxidant activities of the three compounds is studied via the density functional theory (DFT) and time-dependent DFT (TD-DFT) methods. The calculated potential energy curves suggest that the rate of ESIPT reaction will gradually slow down from 5HF to 5HF-OMe and 5HF-NH2. In addition, the antioxidant activities of the three compounds gradually enhance from 5HF to 5HF-OMe and 5HF-NH2, which can be seen from the calculated energy gaps and ionization potential values. Interestingly, the above results imply that the rate of ESIPT reaction has a negative relationship with the antioxidant activities of the compounds, i.e., the slower rate of ESIPT reaction will reflect the higher antioxidant activity of the compound, which will provide valuable reference for detecting the antioxidant activity of compound via the photophysical method.
Keywords:  5-hydroxyflavone      excited state intramolecular proton transfer      antioxidant activity      density functional theory  
Received:  20 February 2020      Revised:  04 March 2020      Published:  05 May 2020
PACS:  82.39.Jn (Charge (electron, proton) transfer in biological systems) (Time-dependent density functional theory) (Ultrafast dynamics; charge transfer)  
Fund: Project supported by the National Basic Research Program of China (Grant No. 2019YFA0307701), the National Natural Science Foundation of China (Grant No. 11874180), and the Science and Technology Development Project of Jilin Province of China (Grant No. 20190103101JH).
Corresponding Authors:  Ying Shi     E-mail:

Cite this article: 

Chaofan Sun(孙朝范), Bifa Cao(曹必发), Hang Yin(尹航), Ying Shi(石英) Relationship between ESIPT properties and antioxidant activities of 5-hydroxyflavone derivates 2020 Chin. Phys. B 29 058202

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