In this study, soluble in water poly(azomethine-ester)s (PAEs) were synthesized via elimination reactions of aromatic dihydroxy compounds containing imine bonding with terephthaloyl chloride. The structures of Schiff bases (SBs) and PAEs containing different aliphatic chains were confirmed by FT-IR, 1H-NMR, 13H-NMR C-NMR and UV-Vis analyses. Physicochemical properties of the new polymers were characterized. Thermal properties of the compounds were investigated by TGA-DTA, DMA and DSC. According to TGA measurements, the starting degradation temperatures (Ton) of P-1, P-2, P-3, and P-4 poly(azomethine-ester)s were found as 255 °C, 232 °C, 222 °C, and 221 °C, respectively. The starting degradation temperatures of the poly(azomethine-ester)s were higher than their Schiff base compounds. According to dynamical mechanical analysis (DMA) measurements, glass transition temperature (Tg) of P-1, P-2, P-3, and P-4 poly(azomethine-ester)s were found as 95 °C, 138 °C, 140 °C, and 145 °C, respectively. The morphological and topographic properties of the PAEs containing azomethine linkage in the main chain were investigated by FE-SEM and AFM, respectively. The molecular mass distributions of PAEs were determined by gel permeation chromatography (GPC). Electrochemical (E′g) and optical band gap (Eoptg ) values of the prepared SBs and PAEs were calculated from cyclic voltammetry (CV) and UV-Vis analyses. The electrochemical band gap (E′g) values of P-1, P-2, P-3 and P-4 were found as 2.44 eV, 2.41 eV, 2.39 eV and 2.39 eV, respectively, from the cyclic voltammetry.