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Synthesis of a Heavy-Atom-Free BODIPY and its Photooxygenation of 1-Naphthol to 1,4-Naphthoquinone

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Using 6,7-dihydro-1H-indol-4(5H)-one, introduction of carbonyl group into BODIPY as photosensitizer was achieved. This heavy-atom-free BODIPY was highly effective singlet oxygen productivity in heavy-atom-free BODIPY system and calculated to be 0.68,… Click to show full abstract

Using 6,7-dihydro-1H-indol-4(5H)-one, introduction of carbonyl group into BODIPY as photosensitizer was achieved. This heavy-atom-free BODIPY was highly effective singlet oxygen productivity in heavy-atom-free BODIPY system and calculated to be 0.68, comparing to that (Φ∆ = 0.57) of methylene blue. Photooxygenation of 1-naphthol into 1,4-naphthoquinone was achieved by this heavy-atom-free BODIPY in present of white light irradiation under air atmosphere. Our work showed a practical example of the design of heavy-atom-free BODIPY leading to efficient singlet oxygen generation with a potential in photocatalysis.

Keywords: naphthol naphthoquinone; atom free; photooxygenation naphthol; free bodipy; heavy atom

Journal Title: Synlett
Year Published: 2023

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