Marek Štancl

Glycoluril Trimers: Selective Synthesis and Supramolecular Properties

The first selective synthesis of glycoluril trimers is described. Trimers framed by o-xylylene walls represent new supramolecular hosts which are able to encapsulate bispyridinium ethylene and methylviologen guests in the solid state and aqueous solution.

Glycoluril Dimers Bearing Hydrogen Atoms on Their Convex Face and Their Self-Assembly in the Solid State

A selective method for the synthesis of 1,6-substituted glycolurils has been developed. The glycolurils have been used for the synthesis of methylene-bridged glycoluril dimers bearing hydrogen atoms on their convex face. Depending on the side walls of the dimers, different modes of self-assembly in the solid state have been described using X-ray crystallography.

Glycoluril Dimer Isomerization under Aqueous Acidic Conditions Related to Cucurbituril Formation

A water-soluble methylene-bridged glycoluril dimer 2S was isolated. It was shown that 2S is the only kinetic product of the reaction between glycoluril derivative 1 and paraformaldehyde. Compound 2S is subsequently intermolecularly transformed into its diastereomer 2C. The kinetics and thermodynamics of the S- to C-shaped dimer isomerization were investigated under reaction conditions similar to those for cucurbituril synthesis.

Synthesis and supramolecular properties of glycoluril tetramer

Synthesis of glycoluril tetramer bearing hydrogen atoms on its convex face and framed by two xylylene units is reported. This tetramer forms dimeric aggregates in the solid state. Host–guest properties of the tetramer with various ammonium and pyridinium guests were determined using 1H NMR spectroscopy. The results were compared with structurally related host molecules.