Abstract

In the course of this work, a new fluorene-based Schiff base compound (SB) from the condensation reaction 2-aminofluorene and 4-(diethylamino)salicylaldehyde was synthesized and its structure was characterized by FTIR, 1H/13C NMR spectroscopies and elemental analysis. Crystal structure of the synthesized compound (SB) was determined single crystal X-ray diffraction study. Crystal structure of the compound was solved in monoclinic unit cell and P21 space group. The molecule shows phenol-imine intramolecular hydrogen bond and molecules are connected by CH····π interactions. The Schiff base compound was then screened for its DNA binding properties by using UV–vis absorption, fluorescence and viscosity studies. All DNA binding data showed that the compound interacts with FSdsDNA via intercalation. The intrinsic DNA binding constant of the compound from UV–vis spectral data was 3.00×104 M−1 which is significantly lower than ethidium bromide (an intercalating agent). The compound was further investigated for colorimetric sensing of metal ions. Colorimetric sensor properties of the compound towards Fe(III), Pb(II), Zn(II), Cu(II), Al(III), Hg(II), Co(II), Mn(II) and Ni(II) ions were investigated in solution. The compound showed selective sensing properties for Cu(II) under 365 nm light. Jobs variation study indicated that the Cu(II) to receptor ratio was 2:1.

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