Akman Feride, Kutlu Buşra
Vocational School of Food, Agriculture and Livestock, Bingol University, 12000 Bingol, Turkey.
Chemistry Program, Institute of Sciences, Bingol University, 12000 Bingol, Turkey.
ACS Omega. 2025 Apr 8;10(15):14884-14907. doi: 10.1021/acsomega.4c10102. eCollection 2025 Apr 22.
This study aimed to find a theoretical solution to the problem of photochemical instability of organic UV filters by changing the solvent environments. For this purpose, the four most important organic filters containing UV-sensitive groups, such as oxybenzone, avobenzone, octinoxate, and padimate O, were first selected, and the theoretically optimized geometries were determined by the density functional theory (DFT) method using the B3LYP/6-31G(d,p) basis set. Frontier molecular orbitals (FMOs) and molecular electrostatic potential (MEP) analyses were conducted to reveal differences in the reactivities of the molecules. The oscillator strengths, absorption wavelengths, and excitation energies in gas, water, ethanol, and -hexane phases were determined with the help of the conductor-like polarizable continuum model (CPCM) and time-dependent density functional theory (TD-DFT) to study the effect of solvents on chemical parameters. In light of the obtained data, Natural localized molecular orbital (NLMO), atoms in molecules (AIM), and natural bond orbital (NBO) analyses were done to determine the stability and UV filtering capacity of the molecules. Additionally, topological and Fukui investigations were included. Molecular docking, ADME (absorption, delivery, metabolism, and excretion) properties, and Hirshfeld surface analysis were conducted. Finally, with the help of the theoretical data obtained, the results in different solvent environments are interpreted and compared with each other.
本研究旨在通过改变溶剂环境找到解决有机紫外线过滤剂光化学不稳定性问题的理论方案。为此，首先选取了四种含有紫外线敏感基团的最重要的有机过滤剂，如二苯甲酰甲烷、阿伏苯宗、桂皮酸盐和对氨基苯甲酸，并用密度泛函理论（DFT）方法，采用B3LYP/6-31G(d,p)基组确定了理论优化几何结构。进行了前线分子轨道（FMO）和分子静电势（MEP）分析，以揭示分子反应性的差异。借助导体类极化连续介质模型（CPCM）和含时密度泛函理论（TD-DFT）确定了气体、水、乙醇和正己烷相中分子的振子强度、吸收波长和激发能，以研究溶剂对化学参数的影响。根据所得数据，进行了自然定域分子轨道（NLMO）、分子中的原子（AIM）和自然键轨道（NBO）分析，以确定分子的稳定性和紫外线过滤能力。此外，还进行了拓扑和福井研究。进行了分子对接、ADME（吸收、递送、代谢和排泄）性质及 Hirshfeld 表面分析。最后，借助获得的理论数据，对不同溶剂环境下的结果进行了解释并相互比较。
