https://doi.org/10.1140/epjp/s13360-025-06723-0
Regular Article
Effects of electronegativity and functional groups on ESIPT and antioxidant activity of acacetin
Xinjiang Normal University School of Physics and Electronic Engineering, Ürümqi, China
a
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Received:
24
May
2025
Accepted:
5
August
2025
Published online:
23
August
2025
Acacetin exhibits unique antioxidant activity due to its excited state intramolecular proton transfer (ESIPT) characteristics, but there is a lack of systematic research on the antioxidant mechanism of acacetin derivatives without the E* state. In this paper, based on density functional theory and time-dependent density functional theory (TD-DFT), the effects of functional group modification and electronegativity regulation on the ESIPT process and antioxidant activity of acacetin derivatives were investigated. Five novel molecules (ACN-CN, ACN-NH2, ANN, ANN-CN, ANN-NH2) were designed by introducing electron-withdrawing/electron-donating groups (–CN, –NH2) and changing the atom-regulated electronegativity (O and N). The results showed that the electron-withdrawing –CN group promoted the ESIPT process, but weakened the antioxidant activity. The electron-donating –NH2 group inhibited the ESIPT process, but significantly enhanced the antioxidant properties. In addition, reducing the electronegativity of the atom will increase the ESIPT energy barrier, but at the same time improve its antioxidant capacity. This study provides a theoretical basis and molecular design strategy for optimizing the antioxidant activity of flavonoids without the E* state, and has guiding significance for the development of high-efficiency antioxidant drugs.
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© The Author(s), under exclusive licence to Società Italiana di Fisica and Springer-Verlag GmbH Germany, part of Springer Nature 2025
Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.
