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Construction of chiral polyesters from polycondensation of multifunctional monomer containing both flexible amino acid and rigid pendant groups with aromatic diols

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Abstract

A number of chiral wholly aromatic polyesters (PEs) with phthalimido and flexible chiral unit in the backbone were prepared from a chiral synthesized diacid monomer, 5-(3-methyl-2-phthalimidylpentanoylamino)isophthalic acid (1), and various aromatic diols via the polyesterification reaction. The tosyl chloride/pyridine/N,N-dimethylformamide (DMF) system was used as a condensing agent. All of the these polymers having bulky phthalimido and amino acid functionalities in the side chain showed excellent solubility and readily dissolved in various solvents such as N-methyl-2-pyrrolidinone, N,N-dimethylacetamide and DMF. Since, these chiral polymers have natural amino acids in the polymer architecture, they are expected to be biodegradable and therefore may be classified under eco-friendly polymers. They had useful levels of thermal stability associated with excellent solubility. Thermogravimetric analysis (TGA) showed that the obtained PEs are rather thermally stable, 10% weight loss temperatures in excess of 317°C, and char yields at 700°C in the nitrogen atmosphere higher than 24%. The resulting polymers were obtained in good yields with inherent viscosities ranging between 0.22 and 0.56 dL/g and were characterized with FT-IR, 1H-NMR, elemental and TGA techniques.

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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. We also like to thank Dr Z. Rafiee and Mr. M. Dinari.

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

    Shadpour Mallakpour & Marziyeh Khani

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  1. Shadpour Mallakpour
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  2. Marziyeh Khani
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Correspondence to Shadpour Mallakpour.

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Mallakpour, S., Khani, M. Construction of chiral polyesters from polycondensation of multifunctional monomer containing both flexible amino acid and rigid pendant groups with aromatic diols. Amino Acids 39, 841–848 (2010). https://doi.org/10.1007/s00726-010-0539-x

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  • DOI: https://doi.org/10.1007/s00726-010-0539-x

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