Journal
DESIGNED MONOMERS AND POLYMERS
Volume 11, Issue 6, Pages 535-546Publisher
TAYLOR & FRANCIS LTD
DOI: 10.1163/156855508X363825
Keywords
Optically active polymers; L-phenylalanine; polyamides; microwave irradiation; diisocyanate route; green chemistry
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Funding
- Research Affairs Division of the Isfahan University of Technology (IUT), Isfahan
- Center of Excellency in Sensors and Green Research (IUT)
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Phthalic anhydride was reacted with L-phenylalanine in N,N-dimethylformamide solution at refluxing temperature, which led to the formation of imide acid. Treatment of this imide acid with excess thionyl chloride gave acid chloride in high yield, which further reacted with 5-aminoisophthalic acid to yield (2S)-5-(3-phenyl-2-phthalimidylpropanoylanimo)isophthalic acid as a bulky chiral aromatic diacid monomer. The polycondensation reaction of this diacid with different aromatic and aliphatic diisocyanates such as 4,4'-methylene bis(4-phenylisocyanate), toluylene-2,4-diisocyanate, hexamethylcne diisocyanate and isophorone diisocyanate was developed by two different methods: microwave-assisted and classical heating in the presence of N-methyl-2-pyrrolidone as a solvent. The polymerization reactions proceeded fast and produced a series of new optically active polyamides (PAs) with good yield and moderate inherent viscosity of 0.25-0.46 dl/g. The resulting PAs are optically active and thermally stable. All of the above compounds were fully characterized by means of FT-IR spectroscopy and specific rotation techniques and typical ones by H-1-NMR, elemental analysis and thermogravimetric analysis. (C) Koninklijke Brill NV, Leiden, 2008
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