Synlett 2024; 35(01): 91-94
DOI: 10.1055/a-2082-0688
cluster
Functional Dyes

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

Meizhu Zhou
,
Xinhu Hu
,
Dongxiang Zhang
,
Tianfang Cui
,

This work was supported by the National Natural Science Foundation of China (Nos. 22078201 and U1908202), the Natural Science Foundation of Liaoning Province (No. 2021NLTS1206), Liaoning & Shenyang Key Laboratory of Functional Dye and Pigment (Nos. 2021JH13/10200018, 21-104-0-23).


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Abstract

By using 1,5,6,7-dihydro-4H-indol-4-one, a carbonyl group was introduced onto a BODIPY photosensitizer. The resulting heavy-atom-free BODIPY is a highly effective producer of singlet oxygen with a calculated quantum yield (ΦΔ) of 0.68, compared with that of methylene blue (ΦΔ = 0.57). Photooxygenation of 1-naphthol to 1,4-naphthoquinone was achieved by using this heavy-atom-free BODIPY catalyst in the presence of white-light irradiation under air atmosphere. Our work demonstrated a practical example of the design of a heavy-atom-free BODIPY, capable of efficient singlet-oxygen generation, with a potential in photocatalysis.

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Publikationsverlauf

Eingereicht: 27. Februar 2023

Angenommen nach Revision: 26. April 2023

Accepted Manuscript online:
26. April 2023

Artikel online veröffentlicht:
26. Mai 2023

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