Mono- and diselenylated fluorescein derivatives: Synthesis using arylseleninic acids as selenylating agents and application as fluorescent probes

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作者：
da Rosa, Kethelyn M. [1 ]
Washio, Nicole M.N. [1 ]
de Quadros, Samara [2 ]
Dreyer, Juliana P. [2 ]
Machado, Vanderlei G. [2 ]
Roehrs, Juliano A. [3 ]
Oliboni, Robson S. [1 ]
Lenardão, Eder J. [1 ]
机构：
[1] Centro de Ciências Químicas, Farmacêuticas e de Alimentos, CCQFA, Universidade Federal de Pelotas, UFPel, P. O. box 354, RS, Pelotas,96010-900, Brazil
[2] Departamento de Química, Universidade Federal de Santa Catarina, UFSC, SC, Florianópolis,CEP: 88035-972, Brazil
[3] Instituto Federal de Educação, Ciência e Tecnologia Sul-rio-grandense, IFSul, RS, Pelotas,CEP: 96015-360, Brazil
来源：
Journal of Molecular Liquids | 2024年 / 416卷
关键词：
Fluorescein and its derivatives are important fluorophores with diverse applications. This study presents an efficient method for synthesizing mono- and diarylselanyl-fluoresceins using arylseleninic acids as selenylating agents in ethanol. This approach yields water and diselenide as by-products; which can be reused; promoting sustainability. We synthesized twelve fluoroprobes; nine of which are novel. The photophysical properties were examined in polar solvents; revealing negative solvatochromism influenced by the selenium atom; which affects fluorescence emission through a photoinduced electron transfer (PET) mechanism. These findings suggest potential applications for these derivatives in analyte detection. © 2024 Elsevier B.V;
D O I：
10.1016/j.molliq.2024.126528
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