In this study, a Schiff base was synthesized by the condensation reaction of 4-bromobenzaldehyde and 4-aminophenol. Then, phenylacetylene substituted Schiff base monomer (IPA) was obtained by HBr elimination reaction of IPA with phenylacetylene through Sonogashira reaction. IPA was polymerized via chemical oxidative polycondensation reaction. FT-IR and NMR measurements were used for the structural analyses of the synthesized substances. Fluorescence and UV-Vis analyses were carried out for optical characterization. Electrochemical characteristics, electrical conductivities and thermal properties were determined using cyclic voltammetry (CV), four-point probe conductometer, TG-DTA and DSC methods. The main purpose of the present study was to investigate the effects of phenylacetylene bearing units on the properties of conjugated aromatic polyimines. The spectral analysis signified a green light emission behavior when irradiated at different wavelengths. Combined with fluorescent behavior and good thermal stability, the electrical conductivity was found to be very crucial for pi-conjugated polymer.