A Simple Water-Soluble ESIPT Fluorescent Probe for Fluoride Ion with Large Stokes Shift in Living Cells.

Abstract

Developing an effective method for monitoring fluoride ion in biological samples is meaningful because fluoride ion plays a vital role in biological processes. In this contribution, a simple water-soluble ESIPT fluorescent probe 2-((4-((tert-butyldiphenylsilyl)oxy)-1,3-dioxoisoindolin-2-yl)methyl)-1-ethylpyridin-1-ium iodide (SPI) was constructed for monitoring fluoride ion. The probe SPI containing pyridinium salt group exhibited preeminent water solubility. The probe SPI introducing a trimethyldiphenylsilyl ether recognition group displayed excellent selectivity for fluoride ion over other biologically relevant species. Additionally, the probe SPI exhibited a fast response for a fluoride ion, suggesting that it could provide real-time fluoride ion detection. Importantly, the probe could detect fluoride ion with a linear range of 0–70.0 × 10–6 M and a low detection limit of 1.16 × 10–6 M. Furthermore, probe SPI could detect fluoride ion with a large Stokes shift (98 nm), which was attributed to ESIPT fluorescence sensing process. At last, probe SPI was successfully employed to monitor fluoride ion in living cells.