Journal
JOURNAL OF SEPARATION SCIENCE
Volume 38, Issue 24, Pages 4211-4215Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/jssc.201500816
Keywords
Azobenzenes; Chiral separation; High-performance liquid chromatography; Liquid-crystalline materials; Photoinduced isomerization
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Funding
- Czech Science Foundation [13-14133S]
- specific university research grant (MSMT) [20/2015]
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Two new types of potential liquid-crystalline azo compounds were synthesized in the form of racemic mixtures and as the individual S enantiomers. Both materials consisting of two substituted aromatic rings in the molecular core and one chiral center at the aliphatic moiety showed mesomorphic behavior. The separation of the R and S enantiomers by chiral high-performance liquid chromatography was unsuccessful when the azo compounds were in their natural E state. However, the irradiation of the compounds in the solution by UV light led to an almost quantitative transition to their Z forms. The chromatographic behavior of the compounds in their Z forms was significantly different, and partial separation of the individual enantiomers on chiral polysaccharide-based stationary phases was obtained. Thus, the proposed procedure represents a novel approach to the enantioseparation of chiral diazenes.
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