Highly selective fluorescence turn-on determination of fluoride ions via chromogenic aggregation of a silyloxy-functionalized salicylaldehyde azine

A novel fluorescent chemsensor TBS-protected salicylaldehyde azine (TSAA) for fluoride ion was developed based on aggregation-induced emission (AIE). The probe TSAA was prepared by the reaction of salicylaldehyde azine (SAA) with tert-butyldimethylsilyl chloride (TBS-Cl) via an unusual synthetic methodology and shows only non-emission. Upon treatment with fluoride in aqueous MeCN solution, the TBS protective group of probe TSAA was removed readily and the fluorescence of the probe was switched on, which resulted in a new fluorescence peak around 543 nm. The fluorescent intensity at 543 nm increases linearly with fluoride ion concentration in the range 1–50 μmol L^?1. This proposed probe shows excellent selectivity toward fluoride ion over other common anions and cations.