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Preparation of NDI-BODIPY Based Photo Catalyzers for Green LED Irradiated Synthesis of Juglone

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Abstract

Photochemistry related studies have been driven by with the application of new types of photocatalysis. Lately boron-dipyrromethene (BODIPY) as distinguished chromophore with exceptional photophysical and chemical features has emerged as a viable photosensitizer. Within this context, three new NDI-BODIPY triads (8–10) were synthesized/ characterized and used to investigate the efficiencies of singlet oxygen generation and oxidation of 1,5-dihydroxynapthalene to juglone under visible light. Singlet oxygen generation was determined both via indirect method by using 1,3-diphenylisobenzofuran as trap molecule and from the characteristic 1O2 phosphorescence at 1270 nm. Also, NDI with BODIPY dyes bearing bromine and iodine atoms were shown to be highly active photocatalysts in which the activities are comparable or higher to the readily available commercial systems where 36% (9) and 66% (10) juglone production was achieved under 15 min. This work may emphasize good example of applying NDI-BODIPY based triads as photocatalysts for a series of important organic transformations.

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All data analyzed in this study are included in this paper and raw data are available to the corresponding author upon reasonable request.

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Funding

This project is funded by the BIDEP 2209-A, Research Project Support Program for Undergraduate Students.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Gebze Technical University, Gebze, P.O.Box: 141, 41400, Kocaeli, Turkey

    Ümmügülsüm Büyükpolat, Ezel Öztürk Gündüz, Hande Eserci Gürbüz & Elif Okutan

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  1. Ümmügülsüm Büyükpolat
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  2. Ezel Öztürk Gündüz
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  3. Hande Eserci Gürbüz
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  4. Elif Okutan
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Contributions

The synthesis of the compounds were done by Ümmügülsüm BÜYÜKPOLAT, Ezel ÖZTÜRK GÜNDÜZ and Hande ESERCİ GÜRBÜZ. Photophysical and photochemical measurements were made by Ümmügülsüm BÜYÜKPOLAT, Ezel ÖZTÜRK GÜNDÜZ and Hande ESERCİ GÜRBÜZ. Data collection, graphing and interpretation of the data were made by all authors and contributed to the results discussion. The publication has been written and reviewed by all authors. All authors have read and approved the final draft.

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Correspondence to Elif Okutan.

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Büyükpolat, Ü., Öztürk Gündüz, E., Eserci Gürbüz, H. et al. Preparation of NDI-BODIPY Based Photo Catalyzers for Green LED Irradiated Synthesis of Juglone. J Fluoresc 33, 2305–2313 (2023). https://doi.org/10.1007/s10895-023-03203-5

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