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An efficient microwave-assisted synthesis of optically active polyamides in the presence of ionic liquid and conventional solvent: a comparative study Shadpour Mallakpour • Zahra Rafiee Received: 1 May 2010 / Revised: 10 June 2010 / Accepted: 10 June 2010 /Published online: 17 June 2010 Springer-Verlag 2010 Monomer synthesis Optically active dicarboxylic acid monomer 8 was synthesized according to previous publications (Scheme 1) [10, 20]. Polymer synthesis In the present study, several optically active PAs containing L-phenylalanine and anthracenic groups were synthesized based on the phosphorylation polyamidation technique of dicarboxylic acid 8 with various aromatic diamines by two systems of the condensing agent under microwave activation and properties of the resulting polymers were compared (Scheme 1). In the first method IL, [1,3-(pr)2im]Br in the presence of TPP was promoted polyamidation reactions, and microwave irradiation was applied as a source of heating for rapid synthesis of PAs and in the second method NMP/Py/TPP/CaCl2 system was employed as condensing agent under microwave activation. The mechanism of activation by TPP/IL is cited in [19]. The higher inherent viscosities and shorter reaction time were advantages of polymerization using method I than method II. The yields and thermal stability of the polymers were comparative under both conditions and all of the obtained PAs are white color. The results of the polymerization reactions are presented in Tables 1 and 2. |
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