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

Organic & Biomolecular Chemistry Pub Date: 2014-08-26 DOI: 10.1039/C4OB01500B

Abstract

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?. 1H 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.

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