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Synthesis and characterization of heterocyclic, and optically active poly(amide-imide)s by phosphorylation polycondensation

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Summary

N,N′-Pyromelliticdiimido-di-L-methionine (1), N,N′-Pyromelliticdiimido-di-L-alanine (2), N,N′-Pyromelliticdiimido-di-L-phenylalanine (3) , and N,N′-Pyromelliticdiimido-di-L-leucine (4) 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. The phosphorylation polycondensation of the corresponding diimide-diacid monomers with 4-phenyl-2,6-bis(4-aminophenyl) pyridine (6) or 4-(p-methylthiophenyl)-2,6-bis(4-aminophenyl) pyridine (8) were carried out in N-methyl-2-pyrolidone (NMP). The resulting poly (amide-imide)s were obtained in quantitative yields, showed admirable inherent viscosities (0.20-0.97 dl g-1), were soluble in polar aprotic solvents, showed good thermal stability and high optical purity. The synthetic compounds were characterized by IR, MS, 1H NMR and 13C NMR spectroscopy, elemental analysis and specific rotation.

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Authors and Affiliations

  1. Pharmaceutical Research Laboratory, College of Chemistry, Isfahan University of Technology, Isfahan, 84156, Iran

    Abdol R. Hajipour & Saeed Zahmatkesh

  2. Department of Pharmacology, University of Wisconsin, Medical School, 1300 University Avenue, Madison, 53706-1532, WI, USA

    Abdol R. Hajipour & Arnold E. Ruoho

  3. Department of Chemistry, College of Science, Shiraz University, Shiraz, 71454, Iran

    Ahmad Banihashemi

Authors
  1. Abdol R. Hajipour
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  2. Saeed Zahmatkesh
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  3. Ahmad Banihashemi
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  4. Arnold E. Ruoho
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Correspondence to Abdol R. Hajipour.

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Hajipour, A., Zahmatkesh, S., Banihashemi, A. et al. Synthesis and characterization of heterocyclic, and optically active poly(amide-imide)s by phosphorylation polycondensation. Polym. Bull. 59, 145–159 (2007). https://doi.org/10.1007/s00289-007-0750-4

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  • DOI: https://doi.org/10.1007/s00289-007-0750-4

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