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.

Mixing of structurally similar self-assembling materials is a powerful tool to tune their mesomorphic, orientational or dielectric properties. We present design and study of binary mixtures composed of two newly designed chiral lactic acid derivatives with a similar structure but different geometry of the molecular core. One compound possesses a monotropic ferroelectric SmC* phase while another shows a direct isotropic – crystalline phase transition. It has been shown that the binary mixtures possess the eutectic behaviour and the ferroelectric phase temperature range has been extended. Moreover, for certain mixtures induced liquid crystalline phases, namely the cholesteric or TGB_A phases, were detected.

Chiral calamitic photoactive materials exhibiting self-assembling behaviour attract substantial interest in the soft matter community due to their high potential for the contactless control of mesomorphic, structural, optical, and dielectric properties via UV/visible light irradiation. To advance the structure-property relationships of this class of smart organic materials, several azobenzene derivatives bearing two electron-withdrawing groups at the 4,4′-positions and chiral derived from lactic acid were designed and characterized. Depending on the molecular structure, these materials preferentially exhibit various chiral liquid crystalline (LC) smectic phases, whereas lateral substitution completely suppresses LC behaviour. The E-Z photoisomerization and thermal Z-E relaxation of these chiral compounds were investigated using high-performance liquid chromatography, and the kinetics of the Z-E relaxation process are discussed. Owing to their slow E/Z switching kinetics, these photoactive materials hold potential for multicomponent mixtures aimed at bistable photonic bandgap tuning, long-term optical data storage, and bistable circularly polarized light modulators.