Papers

Peer-reviewed
Aug, 2015

Influence of Helical Structure on Chiral Recognition of Poly(phenylacetylene)s Bearing Phenylcarbamate Residues of L-Phenylglycinol and Amide Linage as Pendants

CHIRALITY
  • Chunhong Zhang
  • ,
  • Rui Ma
  • ,
  • Hailun Wang
  • ,
  • Ryosuke Sakai
  • ,
  • Toshifumi Satoh
  • ,
  • Toyoji Kakuchi
  • ,
  • Lijia Liu
  • ,
  • Yoshio Okamoto

Volume
27
Number
8
First page
500
Last page
506
Language
English
Publishing type
Research paper (scientific journal)
DOI
10.1002/chir.22453
Publisher
WILEY-BLACKWELL

Four poly(phenylacetylene)s (PPA-1, PPA-2, PPA-3, PPA-4) bearing phenylcarbamate residues of L-phenylglycinol and amide linkage as pendants were prepared to be used as chiral stationary phases (CSPs) for high-performance liquid chromatography (HPLC), and the influences of coating solvents, dimethylformamide (DMF) and tetrahydrofuran (THF), which were used for coating the polymers on silica gel, on the helical structure of the polymers and their chiral recognition abilities were investigated. The structure analysis of PPA-1, PPA-2, PPA-3, PPA-4 by H-1 nuclear magnetic resonance (NMR), size exclusion chromatography (SEC), optical rotation, and circular dichroism (CD) spectra indicated that the polymers possess the cis-transoidal structure with dynamic helical conformation. The polymers in THF seem to have shorter conjugated helical main chains along with a tighter twist conformation than those in DMF. The chiral recognition abilities of PPA-1, PPA-2, PPA-3, PPA-4 with the different helical structures induced by the coating solvents were evaluated as the CSPs in HPLC. The helical structures of PPA-1, PPA-2, PPA-3, PPA-4 induced with THF are preferable for chiral recognition for some racemates compared to those induced with DMF, and higher chiral recognition abilities of PPA-1, PPA-2, PPA-3, PPA-4 were achieved using THF. Chirality 27:500-506, 2015. (c) 2015 Wiley Periodicals, Inc.

Link information
DOI
https://doi.org/10.1002/chir.22453
Web of Science
https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=JSTA_CEL&SrcApp=J_Gate_JST&DestLinkType=FullRecord&KeyUT=WOS:000358643100009&DestApp=WOS_CPL
ID information
  • DOI : 10.1002/chir.22453
  • ISSN : 0899-0042
  • eISSN : 1520-636X
  • Web of Science ID : WOS:000358643100009

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