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

Abstract

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.