3. Optically Active Polymers with Chiral Recognition Ability

  1. Mark M. Green2,
  2. R. J. M. Nolte3 and
  3. E. W. Meijer4
  1. Yoshio Okamoto,
  2. Eiji Yashima and
  3. Chiyo Yamamoto

Published Online: 14 MAY 2004

DOI: 10.1002/0471471895.ch3

Materials-Chirality, Volume 24

Materials-Chirality, Volume 24

How to Cite

Okamoto, Y., Yashima, E. and Yamamoto, C. (2003) Optically Active Polymers with Chiral Recognition Ability, in Materials-Chirality, Volume 24 (eds M. M. Green, R. J. M. Nolte and E. W. Meijer), John Wiley & Sons, Inc., Hoboken, NJ, USA. doi: 10.1002/0471471895.ch3

Editor Information

  1. 2

    Polytechnic University, Brooklyn, New York, USA

  2. 3

    Laboratory of Organic Chemistry, Department of Organic Chemistry, NSRIM, University of Nijmegen, Toernooiveld 1, 6525 ED, Nijmegen, The Netherlands

  3. 4

    Laboratory of Macromolecular and Organic Chemistry, Eindhoven University of Technology, P.O. Box 513, 5600 MB, Eindhoven, The Netherlands

Author Information

  1. Department of Applied Chemistry, Graduate School of Engineering, Nagoya University, Nagoya, Japan 464-8603

Publication History

  1. Published Online: 14 MAY 2004
  2. Published Print: 25 SEP 2003

Book Series:

  1. Topics in Stereochemistry

Book Series Editors:

  1. Scott E. Denmark and
  2. Jay Siegel

ISBN Information

Print ISBN: 9780471054979

Online ISBN: 9780471471899

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Keywords:

  • optically active polymers with chiral recognition ability;
  • vinyl polymers – polymethacrylates – other vinyl polymers;
  • polyamides;
  • other synthetic polymers;
  • natural polymers and their derivatives;
  • proteins;
  • polysaccharides – cellulose esters – cellulose and amylose phenylcarbamates – cellulose and amylose arylalkylcarbamates – cellulose and amylose cycloalkylcarbamates – oligosaccharides and cyclodextrins – other phenylcarbamates of polysaccharides;
  • mechanism of chiral recognition on polysaccharide derivatives – chromatographic studies – NMR studies – computational studies

Summary

Several optically active polymers, such as polymethacrylates, polyacrylamides, polyacetylenes, and polysaccharide derivatives, exhibit high chiral recognition when used as a chiral stationary phase for high-performance liquid chromatography (HPLC). The polymers with high chiral recognition ability generally possess a sterically regular structure, and some of the chiral polymers have been practically used to resolve a wide range of racemates. Among these polymers, polysaccharide esters and carbamates are particularly valuable because of high chiral recognition ability. Chiral recognition mechanisms for these derivatives can also be evaluated at a molecular level through NMR and molecular simulation studies. In this chapter, chiral separation and recognition by stereoregular polymers will be discussed in connection with polymer structures.