Design, synthesis, characterization and cation sensing behavior of amino-naphthoquinone receptor: Selective colorimetric sensing of Cu(II) ion in nearly aqueous solution with mimicking logic gate operation.

An amino-naphthoquione receptor (R1) has been rationally designed, synthesized and characterized using 1 H and 13 C NMR, LCMS and single crystal X-ray diffraction studies. The receptor exhibits an instantaneous colour change from yellow to blue selectively with Cu(II) ions in water-DMF (98:2% v/v) medium. The results of UV-Vis and fluorescence spectral studies indicates that the mechanism of sensing involves formation of a 1:1 complex between R1 and Cu(II) ion. The proposed mechanism has been confirmed through product analysis using FT-IR, UV-Vis, EPR and HRMS studies in addition to magnetic moment and elemental analysis measurements. The formed [Cu(R1)Cl2 ] possess a square planar geometry. The binding constant for the interaction of Cu(II) ion with the present unsubstituted quinone is found to be relatively higher than that with quinones containing electron withdrawing chlorine atom and electron releasing methyl group reported in literature. The detection limit of Cu(II) ion in aqueous solution by R1 is observed to be 8.7nM. The detection of Cu(II) ion by R1 in aqueous solution produces remarkable changes in the electronic and fluorescence spectra, which is applied to construct logic gate at molecular level.