In this study, the oxidative polycondensation reaction conditions of 2,2'-[(2,5-dichloro-1,4-phenylene) bisnitrilomethylylidene]diphenol (DCPMDP) were studied between 40 and 90 degrees C using different times and concentrations in the alkaline medium to determine effect on the yield of these parameters. Polymerization of 2,2'-piperazine-1,4-diylbis[propane-3,1-diylnitrilomethy-lylidene] diphenol (PDMDP) was performed at two steps with graft polycondensation method. Additionally, seven different metal complexes were also synthesized from PDMDP with some metal salts. The structures of the compounds were confirmed by UV-vis, FT-IR, (1)H and (13)C NMR spectroscopy analyses. The characterization was made by TG-DTA, size exclusion chromatography (SEC), elemental analysis, and solubility tests. HOMO-LUMO energy levels and electrochemical band (E(g)(')) gaps were determined from cyclic voltammetry (CV) measurements. Also, optical band (E(g)) gaps were calculated from UV-vis measurements. Electrical conductivity of doped and undoped monomer and oligomer were measured by four-point probe technique using an electrometer. (C) 2011 Wiley Periodicals, Inc. J Appl Polym Sci 120: 3325-3336, 2011