A BODIPY derivative for colorimetric and fluorometric sensing of fluoride ion and its logic gates behavior

A novel BODIPY-based colorimetric and fluorescent sensor with an attached urea group (S1) has been synthesized and characterized by FTIR, NMR, and MS analyses. S1 shows high selectivity and sensitivity toward F- ions among several tested anions (Cl-, Br-, I-, OAc-, NO3-, HSO4-, H2PO4-, CN-) in CHCl3. Upon addition of F- ions, the maximum absorption band of S1 in CHCl3 displayed a red shift from 581 to588 nm. This shift was visually manifested as a color change from pink to blue. When excited at 550 nm, the fluorescent emission intensity of S1 at 608 nm was quenched to over 87% of its initial value. Both a Job'splot and H-1 NMR spectra analysis revealed a 1:1 stoichiometric relationship between S1 and the added F- ions. Moreover, we found that the absorption and fluorescence of the S1-F- complex was reversible upon addition of HSO(4)(-)ions. Finally, by using F- and HSO4- ions as chemical inputs and the absorbance and fluorescence intensity as outputs, a complementary INHIBIT/IMPLICATION (INH/IMP) logic gate was constructed at the nanoscale level. (C) 2014 Elsevier B.V. All rights reserved.