Synthesis and characterization of heterocyclic, and optically active poly(amide-imide)s by phosphorylation polycondensation

Abstract

N,N′-Pyromelliticdiimido-di-L-methionine (1), N,N′-Pyromelliticdiimido-di-L-alanine (2), N,N′-Pyromelliticdiimido-di-L-phenylalanine (3) , and N,N′-Pyromelliticdiimido-di-L-leucine (4) were prepared from the reaction of Pyromellitic dianhydride with corresponding L-amino acids in a mixture of glacial acetic acid and pyridine solution (3/2 ratio) under refluxing conditions. The phosphorylation polycondensation of the corresponding diimide-diacid monomers with 4-phenyl-2,6-bis(4-aminophenyl) pyridine (6) or 4-(p-methylthiophenyl)-2,6-bis(4-aminophenyl) pyridine (8) were carried out in N-methyl-2-pyrolidone (NMP). The resulting poly (amide-imide)s were obtained in quantitative yields, showed admirable inherent viscosities (0.20-0.97 dl g-1), were soluble in polar aprotic solvents, showed good thermal stability and high optical purity. The synthetic compounds were characterized by IR, MS, 1H NMR and 13C NMR spectroscopy, elemental analysis and specific rotation.