Synthesis and properties of new thermally stable and optically active organosoluble poly(ether-amide-imide)s containing bicyclo segment in the main chain

Authors

  • Khalil Faghihi,

    Corresponding author
    1. Organic Polymer Chemistry Research Laboratory, Department of Chemistry, Faculty of Science, Arak University, Arak 38156, Iran
    • Organic Polymer Chemistry Research Laboratory, Department of Chemistry, Faculty of Science, Arak University, Arak 38156, Iran
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  • Meisam Shabanian,

    1. Organic Polymer Chemistry Research Laboratory, Department of Chemistry, Faculty of Science, Arak University, Arak 38156, Iran
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  • Mohsen Hajibeygi,

    1. Organic Polymer Chemistry Research Laboratory, Department of Chemistry, Faculty of Science, Arak University, Arak 38156, Iran
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  • Yasser Mohammadi

    1. Organic Polymer Chemistry Research Laboratory, Department of Chemistry, Faculty of Science, Arak University, Arak 38156, Iran
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Abstract

N,N′-(bicyclo[2,2,2]oct-7-ene-tetracarboxylic)-bis-L-amino acids 3a-f were synthesized by the condensation reaction of bicyclo[2,2,2]oct-7-ene-2,3,5,6-tetracarboxylic dianhydride 1 with two equimolars of L-alanine 2a, L-valine 2b, L-leucine 2c, L-isoleucine 2d, L-phenyl alanine 2e and L-2-aminobutyric acid 2f in an acetic acid solution. Also 1,4-bis[4′-nitrophenoxy]butane 6 was prepared by reaction of 4-nitrophenol 4 with 1,4-dibromo butane 5 in DMF solution. Then dinitro 6 was reduced to 1,4-bis[4′-aminophenoxy]butane 7 by using 10% Pd-C, ethanol and hydrazine monohydrate. Then, six new poly(ether-amide-imide)s PEAIs 8a-f were synthesized through the direct polycondensation reaction of six chiral N,N′-(bicyclo[2,2,2]oct-7-ene-tetracarboxylic)-bis-L-amino acids 3a-f with diamine 7 by direct polycondensation methods in a medium consisting of N-methyl-2-pyrrolidone (NMP)/triphenyl phosphite (TPP)/calcium chloride (CaCl2)/pyridine (Py). The polymerization reaction produced a series of organsoluble and thermally stable poly (ether-amide-imide)s 8a-f with high yield. The resulted polymers were fully characterized by means of FTIR, 1H-NMR spectroscopy, elemental analyzes, inherent viscosity, specific rotation and solubility tests. Data obtained by thermal analysis (TGA and DTG) revealed that these polymers show good thermal stability. © 2010 Wiley Periodicals, Inc. J Appl Polym Sci, 2010

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