Optical chemosensors for Cu(II) ion based on BODIPY derivatives: an experimental and theoretical study |
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Authors: | Tasawan Keawwangchai Banchob Wanno Nongnit Morakot Somchai Keawwangchai |
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Institution: | 1. 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 2. Supramolecular Chemistry Research Unit, Department of Chemistry, Faculty of Science, Mahasarakham University, Maha Sarakham, 44150, Thailand
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Abstract: | Two BODIPY derivatives for Cu2+ ion chemosensors containing 4-2-(diethylamino)-2-oxoethoxy]phenyl (BDP1) and 3,4-bis2-(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 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 Cu2+ to Cu+ ion. Figure Optimized structure, fluorescent spectra, frontier orbital energy diagrams and electron-transfer paths in receptor BDP2 before and after attachment to Cu2+ ion |
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