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Preparation of thermally stable and optically active organosoluble aromatic polyamides containing l-leucine amino acid under green conditions

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Abstract

An optically active bulky dicarboxylic acid (2S)-4-[(4-methyl-2-phthalimidylpentanoylamino)benzoylamino]isophthalic acid (1), was synthesized in five step starting from l-leucine and phthalic anhydride. A set of new aromatic polyamides containing (N-phthaloyl-l-leucine) units was synthesized by the direct one-pot phosphorylation polycondensation of diacid 1 with various aromatic diamines in the presence of different imidazolium salts and triphenyl phosphite (TPP) without adding extra compounds (Method I). This method was compared with a classical method in a medium consisting of TPP, N-methyl-2-pyrrolidinone, pyridine, and calcium chloride (Method II) and the results are comparable. The polymers were produced with high yields and from moderate to high inherent viscosities (0.43–0.81 dL g−1). Amino acid existence in this backbone results in optically active polymers. The chemical structures of some of these polymers were characterized by 1H-NMR and elemental analysis, and all of them with FT-IR and specific rotation tools. By introduction of bulky and flexible clusters in these new polyamides pendent group; make them soluble in most polar aprotic solvents.

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Acknowledgments

We wish to express our gratitude to the Research Affairs Division Isfahan University of Technology (IUT), Isfahan, for partial financial support. Further financial support from National Elite Foundation (NEF) and Center of Excellency in Sensors and Green Chemistry Research (IUT) is gratefully acknowledged.

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Authors and Affiliations

  1. Organic Polymer Chemistry Research Laboratory, Department of Chemistry, Isfahan University of Technology, 84156-83111, Isfahan, Iran

    Shadpour Mallakpour & Mohammad Dinari

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  1. Shadpour Mallakpour
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  2. Mohammad Dinari
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Correspondence to Shadpour Mallakpour.

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Mallakpour, S., Dinari, M. Preparation of thermally stable and optically active organosoluble aromatic polyamides containing l-leucine amino acid under green conditions. Polym. Bull. 63, 623–635 (2009). https://doi.org/10.1007/s00289-009-0113-4

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  • DOI: https://doi.org/10.1007/s00289-009-0113-4

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