β-Lapachone is a natural product with multiple pharmacological activities and mechanistic studies indicated that reactive oxygen species (ROS) generated by β-lapachone play significant roles in its pharmacological actions. As photosensitization is an important ROS-generating pathway, in the present work, the photosensitization mechanisms of β-lapachone are explored on the basis of density functional theory estimated triplet excited state characters. Starting from triplet excited state β-lapachone, the possible generating pathways of 1O2 and O2·– are elucidated and the solvent effects on the photosensitizing reactions are also discussed.
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