Investigation of desilylation in the recognition mechanism to fluoride by a 1,8-naphthalimide derivative.

A reaction-based chemosensor (AF-1) was designed, synthesized and applied as an optical approach for quantitative measurement of F(-) in MeCN. In the presence of F(-), selective fluoride-assisted desilylation instantly gave colorimetric and fluorogenic signals, providing a dual-optical channel for the detection of F(-). (1)H NMR titration was carried out to investigate the desilylation process, revealing F(-) triggered rapid cleavage of Si-O bond in trimethylsilyl ether. AF-1 exhibited high sensitivity and selectivity to F(-) over other anions. The detection limit to F(-) was calculated to be 0.05 ppm.