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Research Article Open access CC BY 4.0

Amphiphilic Fluorescein Triazoles: Synthesis and Visible-Light Catalysis in Water

Alina Artemenko, Elza Sultanova, Diana Mironova, Aliya Akhatova, Ekaterina Bondareva, Daut Islamov, Konstantin Usachev, Svetlana E. Solovieva, Vladimir Burilov, Igor Antipin

Organics · pp. 346–360 · Published 11 Sep 2024

10.3390/org5030018

Abstract

Triazole derivatives of fluorescein-containing N,N-dimethylaminopropyl fragments and their ammonium salts were synthesized with yields of 74–85%. The resulting compounds exhibit fluorescent properties in the green region of the visible spectrum. The critical aggregation concentration (CAC) was estimated using a pyrene fluorescent probe corresponding to a range of 0.28–1.43 mM, and at concentrations above the CAC, the compounds form stable aggregates ranging from 165 to 202 nm. A relative quantum yield of 5–24% has been calculated based on fluorescence and UV spectra. The best value is shown by a derivative containing a tetradecyl substituent. When studying the photocatalytic properties of synthesized compounds through the reaction between N-substituted 1,2,3,4-tetrahydroisoquinoline and malonic ester, the mono-tetradecyl derivative demonstrated the best results. According to gas chromatography–mass spectrometry (GC-MS) data, the conversion of the initial heterocycle reached 95%. Therefore, these resulting compounds have the potential to act as an effective photocatalysts.

Fluorescein Amphiphile Catalysis Visible spectrum Chemistry Photochemistry Materials science Fluorescence

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Cited by 4

Synthesis and Сharacterization of Novel Fluorescein-Based Surfactants

Elza D. Sultanova, Ekaterina A. Bondareva, Alina A. Artemenko · Russian Journal of General Chemistry · 2025

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