Enantioseparation of doubly functionalized polar norbornenes by HPLC and their ruthenium-catalyzed ring-opening metathesis polymerization

Yasushi Nishihara, Yukiko Doi, Seisuke Izawa, Horng Yi Li, Yoshiaki Inoue, Masaaki Kojima, Jwu Ting Chen, Kentaro Takagi

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

A study was conducted to demonstrate enantioseparation of exo-2,3-disubstituted norbornene 1 and the subsequent Ru-catalyzed living ROMP of the obtained optically active norbornene derivatives. The resulting polymers were characterized with various spectra, such as 1H and 13C{H} NMR, UV-vis, and circular dichroism (CD). The influence of the microstructure of the main chain of the prepared polynorbornenes on the optical behavior was discussed, based on polynorbornene backbones. It was observed that the microstructure of polynorbornenes prepared by ROMP depended the relationship between adjacent chain units. The exo-2,3-disubstituted polynorbornene main chain consisted of up to eight different relationships between two units.

Original languageEnglish
Pages (from-to)485-491
Number of pages7
JournalJournal of Polymer Science, Part A: Polymer Chemistry
Volume48
Issue number2
DOIs
Publication statusPublished - Jan 15 2010

Keywords

  • Chiral
  • Cycloolefins
  • Enantioseparation
  • High performance liquid chromatography (HPLC)
  • Norbornenes
  • Optically active polymers
  • ROMP
  • Resolution
  • Ruthenium catalyst

ASJC Scopus subject areas

  • Polymers and Plastics
  • Organic Chemistry
  • Materials Chemistry

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