New complexes of 2,3-bis(5-(4-chlorophenyl)diazenyl)-2-hydroxybenzylideneamino)maleonitrile (CDHBDMN) with VO(II), Mn(II), Co(II), Ni(II), Cu(II), and Zn(II) were synthesized and characterized by analytical and physicochemical techniques, that is, elemental analyses, molar conductivity, UV, IR, EPR, 1 H-NMR spectra, magnetic susceptibility and also by aid of scanning electron microscopy (SEM), nonlinear optical study (NLO), �uorescence spectral studies, and solvatochromic behaviors. Electronic and magnetic susceptibility measurements of the complexes indicate square pyramidal geometry for VO(II), octahedral for Ni(II), and square planar geometry for all the other complexes. e EPR spectral data provide information about their structures on the basis of Hamiltonian parameters and the degree of covalency. ese metal complexes were also tested for their antibacterial and antifungal activities to assess their inhibiting potential. Metal-mediated �uorescence enhancement is observed on complexation of the azo Schiff base ligand. e synthesized compounds were investigated for nonlinear optical properties, and the surface morphology of the Cu(II) complex was studied by scanning electron microscopy.