論文

査読有り
2015年3月

Synthesis and Chiral Recognition of Helical Poly(phenylacetylene)s Bearing L-Phenylglycinol and its Phenylcarbamates as Pendants

JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY
  • Chunhong Zhang
  • ,
  • Hailun Wang
  • ,
  • Taotao Yang
  • ,
  • Rui Ma
  • ,
  • Lijia Liu
  • ,
  • Ryosuke Sakai
  • ,
  • Toshifumi Satoh
  • ,
  • Toyoji Kakuchi
  • ,
  • Yoshio Okamoto

53
6
開始ページ
809
終了ページ
821
記述言語
英語
掲載種別
研究論文(学術雑誌)
DOI
10.1002/pola.27506
出版者・発行元
WILEY-BLACKWELL

A series of novel stereoregular one-handed helical poly(phenylacetylene) derivatives (PPA-1 and PPA-1a similar to g) bearing L-phenylglycinol and its phenylcarbamate residues as pendants was synthesized for use as chiral stationary phases (CSPs) for HPLC, and their chiral recognition abilities were evaluated using 13 racemates. The phenylcarbamate residues include an unsubstituted phenyl, three chloro-substituted phenyls (3-Cl, 4-Cl, 3,5-Cl-2), and three methyl-substituted phenyls (3-CH3, 4-CH3, 3,5-(CH3)(2)). The acidity of the phenylcarbamate N-H proton and the hydrogen bonds formed between the N-H groups of the phenylcarbamate residues were dependent on the type, position, and the number of substituents on the phenylcarbamate residues. The chiral recognition abilities of these polymers significantly depended on the dynamic helical conformation of the main chain with more or less regularly arranged pendants. The chiral recognition abilities seem to be improved by the introduction of substituents on the phenylcarbamate residues, and PPA-1d bearing the more acidic N-H groups due to the 3,5-dichloro substituents, exhibited a higher chiral recognition than the others. PPA-1d showed an efficient chiral recognition for some racemates, and baseline separation was possible for racemates 5, 11, 12, and 15. (C) 2014 Wiley Periodicals, Inc.

Web of Science ® 被引用回数 : 19

リンク情報
DOI
https://doi.org/10.1002/pola.27506
Web of Science
https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=JSTA_CEL&SrcApp=J_Gate_JST&DestLinkType=FullRecord&KeyUT=WOS:000350277500011&DestApp=WOS_CPL

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