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

doi:10.1002/pola.23781

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 Institute for Interdisciplinary Science

Research output: Contribution to journal › Article › peer-review

12 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 language	English
Pages (from-to)	485-491
Number of pages	7
Journal	Journal of Polymer Science, Part A: Polymer Chemistry
Volume	48
Issue number	2
DOIs	https://doi.org/10.1002/pola.23781
Publication status	Published - 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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title = "Enantioseparation of doubly functionalized polar norbornenes by HPLC and their ruthenium-catalyzed ring-opening metathesis polymerization",

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.",

keywords = "Chiral, Cycloolefins, Enantioseparation, High performance liquid chromatography (HPLC), Norbornenes, Optically active polymers, ROMP, Resolution, Ruthenium catalyst",

author = "Yasushi Nishihara and Yukiko Doi and Seisuke Izawa and Li, {Horng Yi} and Yoshiaki Inoue and Masaaki Kojima and Chen, {Jwu Ting} and Kentaro Takagi",

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doi = "10.1002/pola.23781",

language = "English",

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AU - Nishihara, Yasushi

AU - Doi, Yukiko

AU - Izawa, Seisuke

AU - Li, Horng Yi

AU - Inoue, Yoshiaki

AU - Kojima, Masaaki

AU - Chen, Jwu Ting

AU - Takagi, Kentaro

PY - 2010/1/15

Y1 - 2010/1/15

N2 - 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.

AB - 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.

KW - Chiral

KW - Cycloolefins

KW - Enantioseparation

KW - High performance liquid chromatography (HPLC)

KW - Norbornenes

KW - Optically active polymers

KW - ROMP

KW - Resolution

KW - Ruthenium catalyst

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DO - 10.1002/pola.23781

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VL - 48

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EP - 491

JO - Journal of Polymer Science, Part A: Polymer Chemistry

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SN - 0887-624X

IS - 2

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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