Synthesis of organosoluble polyamides with bulky triaryl imidazole pendent group

New unsymmetrical diamine monomer containing triaryl imidazole pendent group, 4-[4-(4,5-diphenyl-1H-imidazol-2-yl)phenoxy]-1,3-benzenediamine, was synthesized via aromatic substitution reaction of 1-chloro-2,4-dinitrobenzene with 4-(4,5-diphenyl-1H-imidazol-2-yl)phenol, followed by palladium-catalyzed hydrazine reduction. This new monomer was further confirmed by FT-IR, 1H NMR and 13C NMR. Novel polyamides having pendant triaryl imidazole group were prepared by the phosphorylation polycondensation of four commercially aromatic dicarboxylic acids with the prepared diamine. Inherent viscosities of polyamides were in the range 0.42–0.53 dL/g indicating formation of medium molecular weight polymers. Polyamides exhibited glass-transition temperature (Tg) in the range 236–265 °C. These polymers are essentially amorphous and were soluble in polar aprotic solvents such as DMF, NMP, DMAc. The 10% weight loss temperatures in air atmosphere, measured by TGA were in the range 350–373 °C indicating their good thermal stabilities.