期刊
JOURNAL OF CHROMATOGRAPHY A
卷 1622, 期 -, 页码 -出版社
ELSEVIER
DOI: 10.1016/j.chroma.2020.461173
关键词
Poly(diphenylacetylene); Chiral recognition; Enantioseparation; Chiral stationary phase; High-performance liquid chromatography; Helical conformation
资金
- JSPS KAKENHI [18H05209, 19K15621]
- World Premier International Research Center Initiative (WPI) of the Ministry of Education, Culture, Sports, Science and Technology (MEXT), Japan
- Grants-in-Aid for Scientific Research [19K15621] Funding Source: KAKEN
Poly(diphenylacetylene) having optically active anilide pendants (poly-1) were synthesized by the condensation reaction of an optically active carboxylic acid with a key precursor polymer containing amino (-NH2) groups, which was prepared by the polymerization of a phthalimide-protected diphenylacetylene monomer using WCl6-Ph4Sn as a catalyst, followed by phthalimide deprotection in the resulting polymer using hydrazine monohydrate. Poly-1 formed a preferred-handed helical conformation (h-poly-1) upon thermal annealing in DMF because of chirality of the pendant group. Poly-1 and h-poly-1 showed different chiral recognition abilities from the analogous poly(diphenylacetylene)s, having the corresponding optically active amide pendants, as chiral stationary phases (CSPs) for high-performance liquid chromatography. The resolution results with the h-poly-l-based CSP were much better than those with the poly-1-based CSP owing to the preferred-handed macromolecular helicity. Among the tested racemates, the h-poly-l-based CSP exhibited superior chiral recognition ability, especially toward binaphthyl compounds and chiral metal complexes. (C) 2020 Elsevier B.V. All rights reserved.
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