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In this study, the oxidative polycondensation reaction conditions of 4- [(thien-2-yl-methylene) amino] phenol (4-TMAP) by using oxidants such as air O2, H 2 O 2  and NaOCl were studied in an aqueous alkaline medium between 313 and 363 °K. The structures of the synthesized monomer and oligomer were confirmed by FT-IR, UV-vis, NMR and elemental analysis. The characterization was made by TG-DTA, size exclusion chromatography (SEC) and solubility tests. At the optimum reaction conditions, the yield of oligo-4-[(thien-2-yl-methylene) amino] phenol (O-4- TMAP) was found to be 36% for air O 2  oxidant, 40% for H 2 O 2  oxidant and 47% for NaOCl oxidant. According to TG analysis, the weight losses of 4-TMAP and O-4- TMAP were found to be 58.11% and 51.38% at 1273°K, respectively. O-4-TMAP was shown higher stability against thermal decomposition. Also, electrical conductivity of the O-4-TMAP was measured, showing that the polymer is a typical semiconductor. The highest occupied molecular orbital (HOMO), the lowest unoccupied molecular orbital (LUMO) and electrochemical energy gaps ( '  gE )  of 4- TMAP and O-4-TMAP were found to be -6.13, -6.02; -2.72, -2.69; 3.41 and 3.33 eV, respectively.

Synthesis, characterization, thermal stability, conductivity and band gaps of monomer and oligo-4-[(thien-2-ylmethylene) amino] phenol