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Optically active and organosoluble poly(amide-imide)s derived fromN,N′-(Pyromellitoyl)bis-l-histidine and various diamines: Synthesis and characterization

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Abstract

An optically active diacid containing the L-histidine moiety was prepared by reacting pyromellitic dianhydride (1,2,4,5-benzenetetracarboxylic acid 1,2,4,5-dianhydride)1 withl-histidine2 in acetic acid, and was polymerized with several aromatic diamines5a-g to obtain a new series of optically active poly(amide-imide)s (PAIs) using two different methods, such as direct polycondensation in a medium consisting ofN-methyl-2-pyrrolidone (NMP)/triphenyl phosphite (TPP)/calcium chloride (CaCl2)/pyridine (Py) and direct polycondensation in a tosyl chloride (TsCl)/pyridine (Py)/N,N-dimethylformamide (DMF) system as a condensation agent. The resulting new polymers6a-g with inherent viscosity was obtained in good yield. The polymers were readily soluble in polar organic solvents, such asN,N-dimethyacetamide (DMAc),N,N-dimethyformamide (DMF), and dimethyl sulfoxide (DMSO). The obtained polymers were characterized by FTIR, specific rotation, elemental analysis as well as1HNMR spectroscopy and gel permeation chromatography (GPC). The thermal stability of the resulting PAIs was evaluated with thermogravimetric analysis techniques under a nitrogen atmosphere.

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Authors and Affiliations

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

    Khalil Faghihi, Meisam Shabanian & Mohsen Hajibeygi

Authors
  1. Khalil Faghihi
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  2. Meisam Shabanian
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  3. Mohsen Hajibeygi
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Correspondence to Khalil Faghihi.

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Faghihi, K., Shabanian, M. & Hajibeygi, M. Optically active and organosoluble poly(amide-imide)s derived fromN,N′-(Pyromellitoyl)bis-l-histidine and various diamines: Synthesis and characterization. Macromol. Res. 17, 912–918 (2009). https://doi.org/10.1007/BF03218635

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  • DOI: https://doi.org/10.1007/BF03218635

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