A novel Schiff base N,N’-bis(3-(4-methoxyphenyl)-1-(thiophen-2-yl)allylidene)-6-phenyl-1,3,5-triazine-2,4-diamine is synthesized by the condensation reaction of 2,4-diamino-6-phenyl-1,3,5-triazine with chalcone [3-(4-methoxyphenyl)-1-(thiophen-2-yl)prop-2-en-1-one]. Metal complexes of the Schiff base ligand with molecular formula ML.Cl2 where, M=Cu(II), Co(II), Zn(II) have been synthesized and characterized on the basis of IR, magnetic susceptibility, UV-Visible, 1H-NMR, EPR spectral studies. From spectral data of the complexes, it have been tentatively assigned as square planar geometry for Cu(II), Zn(II) complexes and tetrahedral geometry for Co(II) complex. The molar conductance of the metal(II) complexes show the non-electrolytic nature of the complexes. The redox behavior of the copper(II) complex was studied by cyclic voltammetry. All the synthesized compounds may serve as potential photoactive materials as indicated from their characteristic fluorescence spectrum. The ligand–ligand charge transfer is reflected in emission spectra and is due to the presence of phenyl rings in the ligands. The nonlinear optical behaviour of the ligand and the metal(II) complexes are investigated and the second harmonic generation efficiency of the complexes have more activity than the organic ligand. The in-vitro antimicrobial activities of the compound were tested against the microorganisms the bacteria Klebsiella pneumonia and the fungi Candida albicans by well diffusion method and the result reveals that the ligand and its metal(II) complexes have significant antimicrobial activity.