Development of New Supramolecular Lyotropic Liquid Crystals and Their Application as Alignment Media for Organic Compounds

Most alignment media for the residual dipolar coupling (RDC) based molecular structure determination of small organic compounds consist of rod‐like polymers dissolved in organic solvents or of swollen cross‐linked polymer gels. Thus far, the synthesis of polymer‐based alignment media has been a challenging process, which is often followed by a time‐consuming sample preparation. We herein propose the use of non‐polymeric alignment media based on benzenetricarboxamides (BTAs), which self‐assemble into rod‐like supramolecules. Our newly found supramolecular lyotropic liquid crystals (LLCs) are studied in terms of their LLC properties and their suitability as alignment media in NMR spectroscopy. Scalable enantiodifferentiating properties are introduced through a sergeant‐and‐soldier principle by blending achiral with chiral substituted BTAs.     

“Inherently Chiral” Ionic‐Liquid Media: Effective Chiral Electroanalysis on Achiral Electrodes

To achieve enantioselective electroanalysis either chiral electrodes or chiral media are needed. High enantiodiscrimination properties can be granted by the “inherent chirality” strategy of developing molecular materials in which the stereogenic element responsible for chirality coincides with the molecular portion responsible for their specific properties, an approach recently yielding outstanding performances as electrode surfaces. Inherently chiral ionic liquids (ICILs) have now been prepared starting from atropisomeric 3,3′‐bicollidine, synthesized from inexpensive reagents, resolved into antipodes without need of chiral HPLC and converted into long‐chain dialkyl salts with melting points below room temperature. Both the new ICILs and shorter family terms, solid at room temperature, employed as low‐concentration additives in achiral ILs, afford impressive enantioselection for the enantiomers of different probes on achiral electrodes, regularly increasing with additive concentration.