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The oxidative polycondensation reaction conditions of 4-m-tolylazomethinephenol (4-TAMP) in the presence of air O₂ and NaOCl as oxidants were studied in an aqueous alkaline medium between 50 and 90°C. The structures of the obtained monomer and oligomer were confirmed by FT-IR, UV-Vis, ¹H- and ¹³C-NMR and elemental analysis techniques. The physical characterization was made by TG-DTA, size exclusion chromatography (SEC) and solubility tests. At the optimum reaction conditions, the yield of oligo-4-m-tolylazomethinephenol (O-4-TAMP) was found to be 62.50% (for air O₂ oxidant) and 90.0% (for NaOCl oxidant), respectively. According to the SEC analysis, the number-average molecular weight (M_n), weight-average molecular weight (M_w) and polydispersity index (PDI) values of O-4-TAMP were found to be 2310, 2610 g mol^-1 and 1.13, respectively, using air O₂, and 1390, 1710 g mol^-1 and 1.23, using NaOCl, respectively. According to TG-DTA analyses, O-4-TAMP was more stable than 4-TAMP against thermal decomposition. The weight losses of 4-TAMP and O-4-TAMP were found to be 68% and 58% at 1000°C. Electrical conductivity of the O-4-TAMP was measured, showing that the polymer is a typical semiconductor. Electrochemically, the highest occupied molecular orbital (HOMO), the lowest unoccupied molecular orbital (LUMO) and electrochemical energy gaps (E′_g) for 4-TAMP are -5.96, -3.22 and 2.74 eV, respectively. The HOMO, LUMO and (E′_g) for O-4-TAMP are -5.78, -3.44 and 2.34 eV, respectively. According to UV-Vis measurements, optical band gaps (E_g) of 4-TAMP and O-4-TAMP were found to be 3.45 and 3.10 eV, respectively.

The optimum reaction conditions of the oxidative polycondensation of 2-(thien-2-yl-methylene)aminophenol (2-TMAP) has been accomplished by using air O₂, H₂O₂ and NaOCl oxidants in an aqueous alkaline medium between 20°C and 90°C. The structures of the monomer and oligomer were confirmed by FT-IR, UV-Vis, ¹H-NMR and ¹³C-NMR and elemental analysis. TGA-DTA, size exclusion chromatography (SEC) techniques and solubility tests were applied for characterization. The ¹H-NMR and ¹³C-NMR data show that the polymerization proceeded with C–C and C–O–C coupling system from ortho and para positions and oxyphenylene. The number-average molecular weight (M_n), weight-average molecular weight (M_w) and polydispersity index (PDI) values of oligo[2-(thien-2-yl-methylene)aminophenol] (O-2-TMAP) were determined with SEC measurements. Thermal analyses of oligomer-metal complex compounds of O-2-TMAP with Cd⁺², Co⁺², Cu⁺², Zn⁺², Fe⁺², Zr⁺⁴, Ni⁺² and Pb⁺² ions were investigated in N₂ atmosphere in the temperature range of 15–1000°C. The highest occupied molecular orbital and the lowest unoccupied molecular orbital of monomer and oligomer were determined from the onset potentials for n-doping and p-doping, respectively. Optical band gaps (E_g) of 2-TMAP and O-2-TMAP and oligomer-metal complex compounds determined according to UV-Vis measurements. Also, electrical conductivities of O-2-TMAP and its metal complexes measured with four-point probe technique.