Synthesis and characterization of novel poly(amide-ether)s bearing imidazole pendants: study of physical and optical properties

Two new para-linked diether-diamines, bis(4-(4-amino-2-(4,5-diphenyl-1H-imidazol-2-yl)phenoxy) phenyl)methanone and bis(4-(4-amino-2-(4,5-diphenyl-1H-imidazol-2-yl)phenoxy) phenyl)hexafluoropropane, bearing two ortho-linked phenyl-substituted imidazole pendants and trifluoromethyl groups were synthesized by the nucleophilic chlorodisplacement reaction of the synthesized 2-(2-chloro-5-nitrophenyl)-4,5-diphenyl-1H-imidazole with 4,4′-dihydroxybenzophenone or 4,4′-(hexafluoroisopropylidene)diphenol in refluxing DMAc in the presence of potassium carbonate. These diamines were utilized to prepare a series of novel poly(amide-ether)s (PAEs) via direct phosphorylation polycondensation with aliphatic and aromatic dicarboxylic acids. The polymeric samples were readily soluble in a variety of organic solvents and formed low-colored and flexible thin films via solution casting. These polymers showed glass-transition temperatures (Tgs) between 204 and 308 °C. Thermal behaviors of the PAEs were characterized by thermogravimetric analysis, and the 10 % weight loss temperatures were found to be in the range of 330–450 °C in N2. The PAEs exhibited fluorescence emission in solution and in solid state with maxima around 423–494 nm and with the quantum yields in the range of 6–28 %.