Excited-state antioxidant capacity of Flavonoids based on solvent effect: A TD-DFT study

作者：Xingzhu Tang, Yajie Zhang, Lei Wang, Lei Wang, Chaofan Sun, Lingling Wang, Lingling Wang, Zhanhua Huang · 发表于：Journal of Molecular Liquids · 年份：2024 · DOI：10.1016/j.molliq.2024.124973 · 被引用次数：14 · 研究领域：Free Radicals and Antioxidants、Phytochemicals and Antioxidant Activities、Antioxidant Activity and Oxidative Stress

Antioxidants have caught a widespread attention because of their applications in various fields such as biomedicine, food additives, cosmetics, and so on, but nevertheless studies on the antioxidant capacity of molecules after photoexcitation are still scarce and rare. In this work, by the application of the density functional theory (DFT) and time-dependent density functional theory (TD-DFT) methods, based on the solvent effect, the antioxidant capacity of 4′-Hydroxyflavone (4′-HF), 6-Hydroxyflavone (6-HF), and 7-Hydroxyflavone (7-HF) in the S 0 and S 1 states are compared. In view of the frontier molecular orbitals (FMOs), depending on the HOMO energy, not only is it analyzed that the electron-donating capacity varies with the solvent, but also that the antioxidant capacity of the mostly molecules in the S 1 state is better than those in the S 0 state, in particular, the 6-HF in ACN in the S 1 state shows a strong antioxidant capacity and is most susceptible to attack by electrophilic radicals, which is also in accordance with the conclusions drawn from the orbital weighted (OW) Fukui functions and OW double descriptors, and global indices including vertical ionization potentials (VIPs), softness ( S ),and so on. Moreover, absorption spectra indicate the potential of these molecules to resist UV radiation and diminished or even quenched fluorescence intensity is caused by intramolecular charge transfer as evidenced by hole-electron analysis. On the basis of the above photop...