The oxidative polycondensation reaction conditions of 2-[(2-hydroxyphenyliminomethylbenzylidene)amino-phenol] (2-HPIMBAP) has been accomplished by using air O2 and NaOCl oxidants in an aqueous alkaline medium between 50－90°C. The optimum reaction conditions of the oxidative polycondensation and the main parameters of the process were established. At the optimum reaction conditions

yield of the products were found to be 67.72% and 61.49% for air O2 and NaOCl oxidants respectively. The structures of the monomer and oligomer were confirmed by FT-IR

UV-Vis

1H-NMR and 13C-NMR and elemental analysis. Also

TGA-DTA

SEC techniques and solubility tests were applied for characterization. 1H-NMR and 13C-NMR data show that the polymerization proceeded by the C―C and C―O―C coupling systems of ortho and para positions and oxyphenylene according to ―OH group of 2-HPIMBAP. The number-average molecular weight (Mn)

weight-average molecular weight (Mw) and polydispersity index (PDI) values of oligo[2-(2-hydroxyphenylimi-nomethylbenzylidene)aminophenol] (oligo(2-HPIMBAP)) were determined. Thermal analyses of oligomer-metal complexes were investigated in N2 atmosphere between 15－1000°C. Electrical conductivities of oligo(2-HPIMBAP) and oligomer-metal complexes measured with four point technique. Electrical conductivity of the oligo(2-HPIMBAP) was measured

showing that the oligomer is a typical semiconductor. Optical band gaps (Eg) of 2-HPIMBAP

oligo(2-HPIMBAP) and oligomer-metal complex compounds were determined by UV-Vis measurements. The monomer and oligomer were screened for antibacterial activities.