Cyclotriveratrylene (CTV) is a C 3-symmetrical macrocycle, which can be used as a chiral building block in the construction of supramolecular containers. Coupling of the CTV unit with a sucrose molecule gave enantiopure water-soluble (after deprotection) containers. The absolute configuration of the synthesized capsules was determined by NMR and ECD spectroscopies and DFT calculations.

The synthesis of four fluorescent diastereoisomeric molecular cages containing cyclotriveratrylene and sucrose moieties connected via the naphthalene linkers is reported. These diastereoisomers were found to be selective and efficient receptors for acetylcholine and choline. Compound P -5a has a better affinity for choline over acetylcholine, while cage M -5a exhibits a higher association constant for acetylcholine over choline. The highest selectivity value was observed for compound M -5a ( K ACh / K Ch = 3.1). Cages P -5a , P -5b , M -5a , and M -5b were fully characterized by the advanced NMR techniques, and ECD spectroscopy was supported by DFT calculations. The binding constants K a of these receptors were determined by fluorescence titration experiments in acetonitrile.

Four diastereomeric molecular cages based on cyclotriveratrylene (CTV) and sucrose scaffolds, connected via p‐phenylene linkers, were synthesized in a few steps synthesis. The absolute configuration of these diastereoisomers was determined by advanced NMR and ECD spectroscopies supported by DFT calculations. The X‐Ray crystal structure of P‐4 b cage gave an insight into its unique structure. The binding properties of P‐4 a and M‐4 a cages towards small ammonium guests (1‐methylpyridinium and 1,3‐dimethylimidazolium salts) were investigated.