Determination of Optical Purity of Lactic Acid-Based Chiral Liquid Crystals and Corresponding Building Blocks by Chiral High-Performance Liquid Chromatography and Supercritical Fluid Chromatography

被引:21
|
作者
Poryvai, Anna [1 ]
Vojtylova-Jurkovicova, Terezia [2 ]
Smahel, Michal [1 ]
Kolderova, Natalie [1 ,3 ]
Tomaskova, Petra [2 ]
Sykora, David [4 ]
Kohout, Michal [1 ]
机构
[1] Univ Chem & Technol Prague, Dept Organ Chem, Tech 5, Prague 16628, Czech Republic
[2] Acad Sci Czech Republ, Inst Phys, Slovance 2, Prague 18221, Czech Republic
[3] Univ Chem & Technol Prague, Forens Lab Biol Act Subst, Tech 3, Prague 16628, Czech Republic
[4] Univ Chem & Technol Prague, Dept Analyt Chem, Tech 5, Prague 16628, Czech Republic
来源
MOLECULES | 2019年 / 24卷 / 06期
关键词
chiral liquid crystals; optical purity; chiral separation; supercritical fluid chromatography; enantioseparation of liquid crystals; mass spectrometry detection; mesomorphic properties; STATIONARY-PHASE; ENANTIOSEPARATION;
D O I
10.3390/molecules24061099
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Liquid crystals (LCs) are among the most prominent materials of the current information age, mainly due to their well-known application in liquid crystal displays (LCDs). Their unique electro-optical properties stem from their ability to form organised structures (mesophases) on the transition from solid state to isotropic liquid. Molecules of LCs in a mesophase still maintain the anisotropy of solid crystals, while simultaneously exhibiting the fluidity of liquids, which gives the system the ability to react immediately to external stimuli such as electric or magnetic fields, light, mechanical stress, pressure and, of course, temperature. For the proper function of LC-based devices, not only chemical, but also optical purity of materials is strongly desirable, since any impurity could be detrimental to the self-assembly of the molecules. Therefore, in this study we aimed to verify synthetic methods published in the literature, which are used nowadays to prepare chiral building blocks based on lactic acid, for their enantioselectivity. Moreover, we have focused on the development of an analytical chiral separation method for target liquid crystalline materials. Using a chiral polysaccharide-based column operated in liquid chromatography mode, we show that not all published methods of LC synthesis are enantioselective, which could lead to significant differences in the properties of the resulting materials. We show that high-performance liquid chromatography with UV detection and supercritical fluid chromatography with UV and mass spectrometry detection enable full control over the chemical and optical purity of the target LCs and the corresponding chiral building blocks. For the first time, we utilise supercritical fluid chromatography with mass detection for the direct chiral analysis of liquid crystalline materials and impurities formed during the synthesis.
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页数:11
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