O-tert-Butyldiphenylsilyl coumarin and dicoumarol: a case toward selective sensing of F− ions in organic and aqueous environments

Abstract

O-tert-Butyldiphenylsilyl coumarin 1 and dicoumarol 2 have been synthesized and their anion binding properties have been examined in organic and aqueous organic solvents. Compound 1 senses F⁻ selectively over the other anions examined in CHCl₃ by exhibiting a greater increase in emission. In contrast, compound 2 shows similar selectivity in CHCl₃ giving ratiometric change in emission as well as color. In addition, both 1 and 2 are capable of detecting F⁻ in water ensuing the cleavage of Si–O bonds. They also show cell permeability and demonstrate their abilities to detect F⁻ in a living system.