Excellent BODIPY Dye Containing Dimesitylboryl Groups as PeT-Based Fluorescent Probes for Fluoride

A highly selective fluorescent probe BBDPB for F- was realized on the basis of the boron-dipyrromethene (BODIPY) dye containing two dimesitylboryl (Mes(2)B) moieties. The fluorophore displays highly efficient orange-red fluorescence with an emission peak of 602 urn and quantum efficiency (Phi) of 0.65 in dichloromethane solution. Signaling changes were observed through UV/vis absorption and photoluminescence spectra. Obvious spectral changes in absorption and fluorescent emission bands were detected after adding F- in company with an obvious solution color change from pink to deep blue. The effects of F- on the electronic structure of BBDPB were studied in detail by performing theoretical calculations using the Gaussian 03 package. According to the theoretical calculation and contrast experiments, the binding of Mes(2)B moieties with F- would give rise to nonradiative photoinduced-electron-transfer (PeT) deactivation from Mes(2)B moieties to BODIPY core and then quench the fluorescence. To implement this approach, an excellent solid-film sensing device was designed by doping BBDPB in polymethylmethacrylate (PMMA).