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A phenylazo appended ortho-vanillin Schiff base scaffold (HAZ) has been used for selective colorimetric sensing of Cu 2+ in semi-aqueous medium (methanol-water, 1:1, v/v) in the presence of 16 cations and 20 anions, and the limit of detection is 1.8 Â 10 À7 M. The structures of HAZ and Cu (II) complex, [Cu (AZ) 2 ], have been characterised by spectroscopic data (UV-Vis, Fourier transform infrared and electron paramagnetic resonance) and established by the single crystal X-ray diffraction measurement. The Job's plot from the absorption studies has also confirmed the 1:2 stoichiometry of Cu 2+ :HAZ. The absorption spectrum of [Cu (AZ) 2 ] has returned to the spectrum of HAZ on the addition of Na 2 EDTA solution which is again recovered upon the addition of Cu 2+ solution. Discrete Fourier transform computations were carried out using the coordinates of the X-ray structures of the compounds, and the molecular functions were used to correlate the solution spectroscopic properties. In addition to this, the probe is treated on MDA-MB 231 breast cancer cells to check the cytotoxicity. The probe is used for the detection of trace quantity of Cu 2+ in the cancer cell. K E Y W O R D Scell imaging assay, cytotoxicity study, colorimetric sensor of Cu 2+ ions, phenylazo appended ortho-vanillin Schiff base, X-ray structures

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