In this study, we proposed to synthesize soluble poly(azomethine-ether)s derivatives containing aromatic rings and long alkyl groups. For this reason, long alkyl groups containing double bromide or chloride atoms were chosen to synthesize diamines monomers (DIAMs). Seven different poly(azomethine-ether)s were synthesized from the condensation reaction of DIAMs with 4,4′-[1,4-phenylenebis(methyleneoxy)]dibenzaldehyde (PBMODB). The structures of compounds were confirmed by FT-IR, UV–Vis, 1H-NMR and 13C-NMR techniques. The molecular weight distributions of synthesized poly(azomethine-ether)s were determined by size exclusion chromatography (SEC). The synthesized compounds were characterized by solubility tests, TG-DTA and DSC. Optical band gaps of poly(azomethine-ether)s (Eg) were also calculated by UV–Vis spectrophotometer. Electrical conductivities of synthesized poly(azomethine-ether)s were measured by four-point probe technique using a Keithley 2400 electrometer. It was stressed that synthesized poly(azomethine-ether)s were found to be insulators which have a potential for electronic and optoelectronic applications, with fairly high band gaps. Thermal stability properties of synthesized poly(azomethine-ether)s were found to be stable up to 300 °C. The chars of them were observed between 33 and 45% at 1000 °C. Poly(azomethine-ether)s containing flexible ether groups and long alkyl chains showed good solubility in aprotic organic solvents.