Yoshinaga Mariana, Toldo Josene M, Rocha Willian R, Barbatti Mario
Laboratório de Estudos Computacionais em Sistemas Moleculares, eCsMo, Departamento de Química, ICEx, Universidade Federal de Minas Gerais, Belo Horizonte, Minas Gerais, Brazil.
University Claude Bernard Lyon 1, ENS de Lyon, CNRS, LCH, UMR 5182, 69342 Lyon cedex 07, France.
Phys Chem Chem Phys. 2025 Jun 11;27(23):12560-12568. doi: 10.1039/d5cp00840a.
-Resveratrol, a naturally occurring antioxidant, undergoes significant photochemical transformations upon UV irradiation, producing photoisomers and derivatives such as -resveratrol, 2,4,6-trihydroxy-phenanthrene (THP), and resveratrone. Using quantum chemical methods, we investigated the photophysical properties of these species, including their absorption spectra, fluorescence, internal conversion (IC), and intersystem crossing (ISC) rates, to assess their potential for singlet oxygen generation. Our results indicate that while - and -resveratrol exhibit limited ISC, resveratrone and THP exhibit competitive ISC and fluorescence rates, making them suitable photosensitizers for singlet oxygen production at the same excitation energy as -resveratrol. However, THP is experimentally more abundant than resveratrone upon -resveratrol excitation and also demonstrates favorable ISC properties, suggesting that it plays a predominant role in singlet oxygen generation. These findings highlight the potential of resveratrone and THP in photodynamic applications, expanding the functional versatility of resveratrol-derived compounds.
白藜芦醇是一种天然存在的抗氧化剂，在紫外线照射下会发生显著的光化学转化，产生光异构体和衍生物，如 -白藜芦醇、2,4,6-三羟基菲（THP）和白藜芦酮。我们使用量子化学方法研究了这些物质的光物理性质，包括它们的吸收光谱、荧光、内转换（IC）和系间窜越（ISC）速率，以评估它们产生单线态氧的潜力。我们的结果表明，虽然 -白藜芦醇和 -白藜芦醇表现出有限的ISC，但白藜芦酮和THP表现出竞争性的ISC和荧光速率，使它们在与 -白藜芦醇相同的激发能量下成为产生单线态氧的合适光敏剂。然而，在 -白藜芦醇激发后，THP在实验上比白藜芦酮更丰富，并且还表现出有利的ISC性质，这表明它在单线态氧的产生中起主要作用。这些发现突出了白藜芦酮和THP在光动力应用中的潜力，扩展了白藜芦醇衍生化合物的功能多样性。
