Dual binding site assisted chromogenic and fluorogenic discrimination of fluoride and cyanide by boryl functionalized BODIPY

A new boron-dipyrromethene (BODIPY) derivative bearing a boronate group (1) had been designed and synthesized as a colorimetric and fluorescent chemosensor for F- and CN- with no interference from each other. The addition of F- and CN- to 1 in THE solution induced a rapid color change from rose pink to indigo and faint pink, respectively. At the same time, the emission color of the 1 changed from red to indigo and green in presence of F- and CN-, respectively. 19F and 1H NMR spectra indicated that the preferential binding of cyanide occurred at the boron center of BODIPY core. On the other hand, fluoride binding occurred at the boron center of BODIPY core and boronate moiety. (C) 2016 Elsevier B.V. All rights reserved.