Extending the Chemistry of Reaction between BODIPY and Cyanide Ions: An Application in Selective Sensing of Fluoride and Cyanide Ions

Abstract

A novel colorimetric BODIPY-based probe for selective detection of fluoride and cyanide has been developed. The color of the solution significantly changes upon addition of fluoride and cyanide ions with detection limits of 2.2 × 10-7and 1.8 × 10-7M calculated by UV-vis absorption method for F-and CN-respectively. An unprecedented phenomenon about the interaction of cyanide ions with the probe was discovered which has not been reported yet. The green color of the paper strip in the presence of cyanide ions changes with time. This observation indicates that unlike fluoride, the cyanide ion interaction with the probe is beyond mere deprotonation of the phenolic group rather envisaged as nucleophilic addition reaction. The phenomenon was also observed in the solution phase and subsequently the reaction order and rate constant of the reaction were determined from absorption versus time graph which were found to be first order and 0.3465 s-1respectively. The emission spectra also showed different behavior of interaction with time for the two ions. The rate of the reaction was found to be independent of the solvent polarity. The plausible mechanism of the reaction between cyanide and fluoride ions with the probe was proposed based on 1H NMR titration experiments and mass spectrometry.