Synthesis of chiral polymers having camphanediol moieties and their applications on the optical resolution of some racemates

Jui-Hsiang Liu, Fu‐Ren ‐R Tsai, Yuh‐Chung ‐C Lai

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

Optically active exo‐exo‐2,3‐camphanediol (CPO) (3) was synthesized from (+)‐camphor. Chiral polymers poly(CPO‐co‐TDI) (6) and poly(CPO‐co‐IPDI) (7) were synthesized by the step polymerization of chiral compound CPO (3) with toluene‐2,4‐diisocyanate (TDI) and isophorone diisocyanate (IPDI). To investigate the stereo structure of the chiral polymers, two kinds of model compounds, exo‐exo‐2,3‐di[(phenylamido)oxy]camphane (4) and exo‐exo‐2,3‐di[(propylamido)oxy]camphane (5), related to polymers (6) and (7) were synthesized. Chiroptical characteristics and stereo structures of the chiral polymers were investigated using a circular dichroic spectrometer. The results obtained in this investigation suggest that the chiral polymers (6) and (7) have no one‐handed helix conformation. The optical resolution ability as chiral adsorbent for HPLC of the chiral polymers was investigated. It was found that chiral polymers (6) and (7) are effective for the optical resolution of some racemates. © 1995 John Wiley & Sons, Inc.

Original languageEnglish
Pages (from-to)1713-1720
Number of pages8
JournalJournal of Applied Polymer Science
Volume58
Issue number10
DOIs
Publication statusPublished - 1995

Fingerprint

Polymers
Camphor
Adsorbents
Conformations
Spectrometers
Polymerization
camphane

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Surfaces, Coatings and Films
  • Polymers and Plastics
  • Materials Chemistry

Cite this

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title = "Synthesis of chiral polymers having camphanediol moieties and their applications on the optical resolution of some racemates",
abstract = "Optically active exo‐exo‐2,3‐camphanediol (CPO) (3) was synthesized from (+)‐camphor. Chiral polymers poly(CPO‐co‐TDI) (6) and poly(CPO‐co‐IPDI) (7) were synthesized by the step polymerization of chiral compound CPO (3) with toluene‐2,4‐diisocyanate (TDI) and isophorone diisocyanate (IPDI). To investigate the stereo structure of the chiral polymers, two kinds of model compounds, exo‐exo‐2,3‐di[(phenylamido)oxy]camphane (4) and exo‐exo‐2,3‐di[(propylamido)oxy]camphane (5), related to polymers (6) and (7) were synthesized. Chiroptical characteristics and stereo structures of the chiral polymers were investigated using a circular dichroic spectrometer. The results obtained in this investigation suggest that the chiral polymers (6) and (7) have no one‐handed helix conformation. The optical resolution ability as chiral adsorbent for HPLC of the chiral polymers was investigated. It was found that chiral polymers (6) and (7) are effective for the optical resolution of some racemates. {\circledC} 1995 John Wiley & Sons, Inc.",
author = "Jui-Hsiang Liu and Tsai, {Fu‐Ren ‐R} and Lai, {Yuh‐Chung ‐C}",
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Synthesis of chiral polymers having camphanediol moieties and their applications on the optical resolution of some racemates. / Liu, Jui-Hsiang; Tsai, Fu‐Ren ‐R; Lai, Yuh‐Chung ‐C.

In: Journal of Applied Polymer Science, Vol. 58, No. 10, 1995, p. 1713-1720.

Research output: Contribution to journalArticle

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AU - Tsai, Fu‐Ren ‐R

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PY - 1995

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AB - Optically active exo‐exo‐2,3‐camphanediol (CPO) (3) was synthesized from (+)‐camphor. Chiral polymers poly(CPO‐co‐TDI) (6) and poly(CPO‐co‐IPDI) (7) were synthesized by the step polymerization of chiral compound CPO (3) with toluene‐2,4‐diisocyanate (TDI) and isophorone diisocyanate (IPDI). To investigate the stereo structure of the chiral polymers, two kinds of model compounds, exo‐exo‐2,3‐di[(phenylamido)oxy]camphane (4) and exo‐exo‐2,3‐di[(propylamido)oxy]camphane (5), related to polymers (6) and (7) were synthesized. Chiroptical characteristics and stereo structures of the chiral polymers were investigated using a circular dichroic spectrometer. The results obtained in this investigation suggest that the chiral polymers (6) and (7) have no one‐handed helix conformation. The optical resolution ability as chiral adsorbent for HPLC of the chiral polymers was investigated. It was found that chiral polymers (6) and (7) are effective for the optical resolution of some racemates. © 1995 John Wiley & Sons, Inc.

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