One-pot polyamidation reaction of optically active aromatic diacid containing methionine and phthalimide moieties with aromatic diamines under microwave irradiation and traditional heating

An optically active diacid containing phthalimide and L-methionine moiety was prepared in three steps, and was polymerized with several aromatic diamines to obtain a new series of optically active polyamides (PAs) through direct polyamidation using triphenyl phosphate/pyridine/N-methyl-2-pyrrolidone/CaCl2 system as condensing agent. The polymerization reactions were carried out under both conventional heating and microwave-assisted irradiation. The data obtained by these methods indicate that, high yields and similar inherent viscosities are resulted. It is worth to mention that in the case of microwave conditions, a drastic decrease in reaction time (3 min vs. 5 h) and cleaner reaction have been achieved. These polymers are readily soluble in polar organic solvents such as N,N-dimethyacetamide, N,N-dimethyformamide, dimethyl sulfoxide. The obtained polymers were characterized by FT-IR, specific rotation measurements, elemental analysis and H-1 NMR techniques. The thermal stability of the resulting PAs were evaluated with thermogravimetric analysis and differential scanning calorimetry techniques under a nitrogen atmosphere which indicate they are moderately stable. (C) 2008 Elsevier Ltd. All rights reserved.