Ionic liquid catalyzed synthesis and characterization of heterocyclic and optically active poly (amide-imide)s incorporating L-amino acids.
N,N'-pyromelliticdiimido-di-L-alanine (1), N,N'-Pyromelliticdiimido-di-L-phenylalanine (2), and N,N'-Pyromelliticdiimido-di-L-leucine (3) 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. A series of poly (amide-imide)s containing L-amino acids were prepared from the synthesized dicarboxylic acids with two synthetic aromatic diamines in an ionic liquid (IL) as a green, safe and eco-friendly medium and also reactions catalysis agent. Evaluation of data shows that IL is the better polyamidation medium than the reported method and the catalysis stand on the higher inherent viscosities of the obtained PAIs and the rate of polymerizations beyond the greener reaction conditions and deletion of some essential reagents in conventional manners. Characterization were performs by means of IR, MS and (1)H NMR spectroscopy, elemental analysis, specific rotation, thermogravimetric analysis and differential scanning calorimetric techniques. Molecular weights of the obtained polymers were evaluated viscometrically, and the measured inherent viscosities were in the range 0.43-0.85 dL/g. These polymers were readily soluble in many organic solvents. These polymers still kept good thermal stability with glass transition temperatures in the range of 94-154°C, and the decomposition temperature under the nitrogen atmosphere for 10% weight-loss temperatures in excess of 308°C.
Zahmatkesh
Saeed
S
Department of Science, Payame Noor University, Tehran, Iran. zahmatkesh1355@yahoo.com
D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D000596:Amino Acids / Q000737:chemistry*; D002384:Catalysis; D007094:Imides / Q000138:chemical synthesis* / Q000737:chemistry; D052578:Ionic Liquids / Q000737:chemistry*; D058105:Polymerization; D011108:Polymers / Q000138:chemical synthesis* / Q000737:chemistry
D000577:Amides; D000596:Amino Acids; D007094:Imides; D052578:Ionic Liquids; D011108:Polymers