Selective Recognition of Fluoride by using a Benzobisimidazolium Derivative through Aggregation-Induced Fluorescence

Abstract

A new benzobisimidazolium derivative (1) bearing four naphthalene moieties was synthesized and demonstrated as an F- ion-selective fluorescent chemosensor. The fluorescence of 1 in acetonitrile (CH3CN) is significantly stronger with F- and acetate (CH3CO2-), but not with other anions (Cl-, Br-, I-, HSO4-, and H2PO4-). The fluorescence of 1 is enhanced selectively with F- in the presence of a small amount of water. Our DFT calculations indicate that the electrostatic interactions between the positively charged benzobisimidazolium moieties and F- play an important role in the formation of stable aggregates. The formation of stable aggregates of 1 with F- in CH3CN is a key step for the selective sensing of F-, and the fluorescence of the aggregates is further enhanced in a mixture of 95% CH3CN and 5% water, which can be attributed to the aggregation-induced emission.