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Synthesis and characterization of novel organosoluble and optically active aromatic polyesters containing l-methionine and phthalimide pendent groups

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Abstract

5-(4-Methylthio-2-phthalimidylbutanoylamino)isophthalic acid (5) as a novel diacid monomer containing phthalimide and flexible chiral groups was prepared by dehydration of l-methionine and phthalic anhydride followed by reacting with thionyl chloride and then treating with 5-aminoisophthalic acid (5AIPA) in dry N,N-dimethylacetamide (DMAc). A series of novel polyesters (PEs) containing phthalimide group was prepared by the reaction of diacid monomer 5 with several aromatic diols via direct polyesterification with tosyl chloride/pyridine/dimethylformamide (DMF) system as condensing agent. The resulting new polymers were obtained in good yields and inherent viscosities ranging between 0.21 and 0.51 dLg−1 were characterized with FT-IR, 1H NMR, elemental and thermogravimetric analysis techniques. These polymers are readily soluble in polar organic solvents such as DMAc, DMF, dimethyl sulfoxide and protic solvents such as sulfuric acid. Specific rotation experiments demonstrate the optical activity induction due to successful insertion of l-methionine in the structure of pendent groups. Thermogravimetric analysis showed that the 10% weight loss temperature in a nitrogen atmosphere were more than 315°C, which indicates that the resulting PEs have good thermal stability.

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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 Center of Excellency in Sensors and Green Chemistry Research (IUT) is gratefully acknowledged. We also extend our thanks to Miss. Z. Rafiee and Dr. M. Kolahdoozan for helpful discussions.

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

    Shadpour Mallakpour & Hojjat Seyedjamali

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  1. Shadpour Mallakpour
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  2. Hojjat Seyedjamali
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Correspondence to Shadpour Mallakpour.

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Mallakpour, S., Seyedjamali, H. Synthesis and characterization of novel organosoluble and optically active aromatic polyesters containing l-methionine and phthalimide pendent groups. Amino Acids 34, 531–538 (2008). https://doi.org/10.1007/s00726-007-0005-6

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  • DOI: https://doi.org/10.1007/s00726-007-0005-6

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