Preprint Article Version 1 Preserved in Portico This version is not peer-reviewed

Amphiphilic Fluorescein Triazoles: Synthesis and Visible Light Catalysis in Water

Version 1 : Received: 24 July 2024 / Approved: 24 July 2024 / Online: 25 July 2024 (09:25:10 CEST)

How to cite: Artemenko, A.; Sultanova, E.; Mironova, D.; Akhatova, A. E.; Bondareva, E.; Islamov, D. R.; Usachev, K.; Solovieva, S. E.; Burilov, V.; Antipin, I. S. Amphiphilic Fluorescein Triazoles: Synthesis and Visible Light Catalysis in Water. Preprints 2024, 2024072001. https://doi.org/10.20944/preprints202407.2001.v1 Artemenko, A.; Sultanova, E.; Mironova, D.; Akhatova, A. E.; Bondareva, E.; Islamov, D. R.; Usachev, K.; Solovieva, S. E.; Burilov, V.; Antipin, I. S. Amphiphilic Fluorescein Triazoles: Synthesis and Visible Light Catalysis in Water. Preprints 2024, 2024072001. https://doi.org/10.20944/preprints202407.2001.v1

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 py-rene 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 deriva-tive 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.

Keywords

CuAAC; photocatalysis; fluorescein derivatives; aggregation

Subject

Chemistry and Materials Science, Organic Chemistry

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