The oxidative polycondensation reaction conditions of 2-[(4-chlorophenyl) imino methylene] phenol (CPIMP) were studied by air O-2 and NaOCl oxidants at various temperatures and times. Optimum reaction conditions of air O-2 and NaOCl were determined for CPIMP. Oligo-2-[(4-chlorophenyl) imino methylene] phenol (OCPIMP) was synthesized from the oxidative polycondensation of CPIMP with air O-2 and NaOCl in alkaline medium between 50 and 90 degrees C. The number-average molecular weight (M-n) weight-average molecular weight (M-n) and polydispersity index (PDI) values of OCPIMP were found to be 470 g mol(-1), 895 g mol(-1), and 1.90, using NaOCl, and 455 g mol(-1), 765 g mol(-1), and 1.68, using air O-2, respectively. At the optimum reaction conditions, the yield of OCPIMP was found to be 62.80% (for air O-2 oxidant) and 87.50% (for NaOCl oxidant). The OCPIMP was characterized by H-1-NMR, FT-IR, UV-Vis and elemental analysis. The thermogravimetric (TGA)-DTA analyses were shown to be stable of OCPIMP and its oligomer metal complexes (such as Co+2, Ni+2, and Cu+2) against thermo-oxidative decomposition. The weight loss of OCPIMP and its oligomer metal complexes (such as Co+2, Ni+2, and Cu+2) were found to be 98%, 85%, 80%, and 82%, respectively, at 1000 degrees C.