%0 Journal Article %A Basa, Prem N. %A Sykes, Andrew G. %D 2016 %T Differential Sensing of Zn(II) and Cu(II) via Two Independent Mechanisms %U https://acs.figshare.com/articles/journal_contribution/Differential_Sensing_of_Zn_II_and_Cu_II_via_Two_Independent_Mechanisms/2480506 %R 10.1021/jo301193n.s001 %2 https://acs.figshare.com/ndownloader/files/4123186 %K presence %K NaBH 4 %K analysis results %K colorimetric change %K metal ion response %K anthracene fluorophore formation %K competition studies %K hydrolysis phenomenon %K 1 H NMR %K XRD %K Lewis base %K fluorescence data %K Zn %K UV %K FTIR %K spectroscopic changes %K 1.0 equiv %K Cu %K 13 C NMR %K Spectroscopic investigations %K Independent MechanismsSelective reduction %K imine hydrolysis %X Selective reduction of an anthracenone–quinoline imine derivative, 2, using 1.0 equiv of NaBH4 in 95% ethanol affords the corresponding anthracen-9-ol derivative, 3, as confirmed by 1H NMR, 13C NMR, ESI-MS, FTIR, and elemental analysis results. UV–vis and fluorescence data reveal dramatic spectroscopic changes in the presence of Zn­(II) and Cu­(II). Zinc­(II) coordination induces a 1,5-prototropic shift resulting in anthracene fluorophore formation via an imine–enamine tautomerization pathway. Copper­(II) induces a colorimetric change from pale yellow to orange-red and results in imine hydrolysis in the presence of water. Spectroscopic investigations of metal ion response, selectivity, stoichiometry, and competition studies all suggest the proposed mechanisms. ESI-MS analysis, FTIR, and single-crystal XRD further support the hydrolysis phenomenon. This is a rare case of a single sensor that can be used either as a chemosensor (reversibly in the case of Zn­(II)) or as a chemodosimeter (irreversibly in the case of Cu­(II)); however, the imine must contain a coordinating Lewis base, such as quinoline, to be active for Cu­(II). %I ACS Publications