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Updated: Jul 16, 2025

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Alcoholic Solvent-Mediated Excited-State Proton Transfer Dynamics of a Novel Dihydroxynaphthalene Dye
Gi Rim Han1, Eunhak Lim1, Jooyeon Kang1
1Department of Chemistry, Seoul National University, Seoul 08826, Republic of Korea.
Abstract:
The excited-state proton transfer (ESPT) reaction is an important primary photochemical process because it is closely related to photophysical properties. Although ESPT research in aqueous solutions is predominant, alcoholic solvent-mediated ESPT studies are also significant in terms of photoacid-based reactions. Especially, the research for dihydroxynaphthalenes (DHNs) has been largely neglected due to the challenging data interpretation of two hydroxyl groups. A novel fluorescent dye, resveratrone, synthesized by light irradiation of resveratrol, which is famous for its antioxidant properties, can be regarded as a type of DHN, and it has distinctive optical properties, including high quantum yield, a large two-photon absorption coefficient, a large Stokes shift, and very high biocompatibility. In this study, we investigate the overall kinetics of the optical properties of resveratrone and find evidence for alcoholic solvent-mediated ESPT involvement in the radiative properties of resveratrone with a large Stokes shift. Our investigation provides an opportunity to revisit the overlooked photophysical properties of intriguing photoacid behavior and the large Stokes shift of the dihydroxynaphthalene dye.
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