Influence of photoinduced isomerization on the chiral separation of novel liquid crystalline materials with a diazene moiety

The influence of photoinduced isomerization on the enantiomeric separation of two newly synthesized liquid crystalline materials, liquid crystals 1 and 2, was studied by high-performance liquid chromatography on a chiral stationary phase Chiralpack AD-3. Both materials have one chiral center and one diazene moiety. The compounds were separated into their E and Z isomeric forms. The conditions and time scale of the ultraviolet-induced E to Z transition were briefly evaluated. Under the optimized conditions, we were able to baseline separate the S and R enantiomers of both the studied materials in their E isomeric form. The chiral separation of liquid crystal 2 after ultraviolet irradiation was unsuccessful. In contrast, the chiral separation of liquid crystal 1 possessing a similar structure to liquid crystal 2 provided baseline separation in its Z isomeric form as well. Previously, we have shown the influence of photoinduced isomerization and its utilization in the enantioseparation on relatively simple molecules. Here, we demonstrate that (1) much more complex compounds can also be successfully separated despite the bulkiness of the achiral part of the structure and (2) photoinduced isomerization even for such complex molecules still strongly influences their chromatographic properties.