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Preparation and characterization of novel optically active poly(vinyl alcohol-co-vinyl ester) in nonaqueous medium using l-phenylalanine as a chiral material

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Abstract

In this investigation, poly(vinyl alcohol) was chemically modified by the introduction of different amounts of N-phthaloyl-l-phenylalanine. The modification was carried out by the reaction of PVA hydroxyl groups with (2S)-3-phenyl-2-phthalimidylpropanoyl chloride using N,N-dimethyl acetamide/lithium chloride as a reaction media. The novel copolymers obtained were characterized by spectroscopic techniques, elemental analysis, X-ray diffraction and thermal methods. Optical rotation and viscosities were also measured. The degree of esterification was determined by 1H-NMR. The influence of reagent molar ratio on the degree of modification was also evaluated. The vinyl(3-phenyl-2-phthalimidopropanoate) content in the copolymer was attained up to 52%. Thermal stability of the copolymers was checked by thermogravimetric analysis and differential thermogravimetric analysis. All copolymers displayed improved thermal stability compared to the parent polymer.

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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 Mr. M. Hatami and Mr. M. Dinari for their valuable help.

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Authors and Affiliations

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

    Shadpour Mallakpour

  2. Nanotechnology and Advanced Materials Institute, Isfahan University of Technology, 84156-83111, Esfahān, Islamic Republic of Iran

    Shadpour Mallakpour & Abdolvahid Barati

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  1. Shadpour Mallakpour
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  2. Abdolvahid Barati
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Correspondence to Shadpour Mallakpour.

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Mallakpour, S., Barati, A. Preparation and characterization of novel optically active poly(vinyl alcohol-co-vinyl ester) in nonaqueous medium using l-phenylalanine as a chiral material. Amino Acids 42, 1287–1295 (2012). https://doi.org/10.1007/s00726-010-0823-9

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  • DOI: https://doi.org/10.1007/s00726-010-0823-9

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