ArticleACS omega2026
Hydroxy-Group Topology as a Molecular Trigger Between Antioxidant and Photosensitizing Properties in Dihydroxynaphthalenes.
Article in ACS omega, 2026. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.
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6 authors.
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Abstract
Dihydroxynaphthalenes (DHN) provide a simple molecular platform to probe how hydroxy-group topology governs the interplay between antioxidant activity and photoinduced reactive oxygen species generation. Four regioisomeric dihydroxynaphthalenes (1,3-, 1,5-, 1,8-, and 2,7-DHN) have been investigated by combining steady-state spectroscopy, time-correlated single-photon counting, and femtosecond transient absorption with functional assays. The results show that intramolecular hydrogen bonding and π-electron delocalization control excited-state relaxation pathways, determining the balance between nonradiative energy dissipation and intersystem crossing. Peri-hydrogen-bonded 1,8-DHN exhibits the highest radical-scavenging efficiency while suppressing triplet formation and singlet-oxygen generation, whereas isomers lacking intramolecular hydrogen bonding display enhanced photosensitizing behavior. These findings establish hydroxy-group topology as a key structural parameter linking ground-state redox chemistry with excited-state photophysics.
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