title: Optical chemosensors for Cu(II) ion based on BODIPY derivatives: an experimental and theoretical study.
abstract: Two BODIPY derivatives for Cu(2+) 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(+), Ca(2+), Fe(2+), Ni(2+), Cu(2+), Zn(2+), Cd(2+), Hg(2+) and Pb(2+) 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 Cu(2+) ion was added. To explain this behavior, ab initio quantum chemical calculations were performed using correlated second-order Møller-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 Cu(2+) to Cu(+) ion.
authors.affiliation: The Center of Excellence for Innovation in Chemistry (PERCH-CIC) and Supramolecular Chemistry Research Unit, Department of Chemistry, Faculty of Science, Mahasarakham University, Maha Sarakham, 44150, Thailand, k.tasawan@gmail.com.
authors.forename: Tasawan
authors.initials: T
authors.lastname: Keawwangchai
authors.forename: Banchob
authors.initials: B
authors.lastname: Wanno
authors.forename: Nongnit
authors.initials: N
authors.lastname: Morakot
authors.forename: Somchai
authors.initials: S
authors.lastname: Keawwangchai