Optical chemosensors for Cu(II) ion based on BODIPY derivatives: an experimental and theoretical study
Two BODIPY derivatives for Cu2+ ion chemosensors containing 4-[2-(diethylamino)-2-oxoethoxy]phenyl (BDP1) and 3,4-bis[2-(diethylamino)-2-oxoethoxy]phenyl (BDP2) were synthesized by coupling appropriate N,N-diethyl-2-(4-formylphenoxy)acetamide and 2,4-dimethylpyrrole moieties in the presence of trifluoroacetic acid and anhydrous dichloromethane at room temperature. The binding abilities between these chemosensors and 50 equivalents of Na+, K+, Ag+, Ca2+, Fe2+, Ni2+, Cu2+, Zn2+, Cd2+, Hg2+ and Pb2+ ions were studied using UV-vis and fluorescence spectrophotometry. The results show that, compared to other ions, both the UV-vis absorption and fluorescence emission intensity of BDP2 decreased dramatically when Cu2+ ion was added. To explain this behavior, ab initio quantum chemical calculations were performed using correlated second-order Moller-Plesset perturbation theory (MP2/LanL2DZ). The calculated orbital energies indicated that the decrease in UV-vis absorption intensity and the quenching of fluorescene emission were due to the single-electron reduction of Cu2+ to Cu+ ion.
chemosensor bodipy fluorescence mp2 lanl2dz dft