Vladimír Šindelář

Bambus[n]urils: a new family of macrocyclic anion receptors.

A recently discovered anion receptor is jointed by three related macrocycles differing in the number of glycoluril units and type of substitution. The synthesis is carried out in nonpolar solvents compared to aqueous media used in the case of the original macrocycle. The size of macrocycle is controlled by a template. A hexameric macrocycle with benzyl substitution binds halide anions with an affinity exceeding 10(9) M(-1) while a tetrameric analog does not bind any of the investigated anions.

Anion Binding by Bambus[6]uril Probed in the Gas Phase and in Solution

Electrospray ionization mass spectrometry (ESI-MS) is used to probe the binding of small anions to the macrocycle of bambus[6]uril. For the halide ions, the experimental patterns suggest F(-) < Cl(-) < Br(-) < I(-), which is consistent with the order of anion binding found in the condensed phase. Parallel equilibrium studies in the condensed phase establish the association constants of halide anions and bambus[6]uril in mixed solvents. A detailed analysis of the mass spectrometric data is used to shed light on the correlations between the binding constants in the condensed phase and the ion abundances observed using ESI-MS. From the analysis it becomes apparent that ESI-MS can indeed represent the situation in solution to some extent, but the sampling in the gas-phase experiment is not 1:1 compared to that in solution.

Supramolecular Shuttle Based on Inclusion Complex between Cucurbit[6]uril and Bispyridinium Ethylene

Cucurbit[6]uril (CB6) and bispyridinium ethylene form a stable inclusion complex. A rotaxane derived from this complex was prepared in which a CB6 wheel shuttles along an axle in an NMR time-resolved regime.

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.

Pressocucurbit[5]uril

A novel macrocycle, decamethylpressocucurbit[5]uril (Me10prCB[5]), was synthesized by acid-catalyzed condensation of propanediurea and paraformaldehyde. This macrocycle binds methane with higher affinity than cucurbit[5]uril and its permethylated derivative.

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.

Chiral Bambusurils for Enantioselective Recognition of Carboxylate Anion Guests

Synthesis of the first enantiomerically pure chiral bambusurils is reported. The bambusurils were prepared on the gram scale without using any chromatography techniques. The bambusurils formed supramolecular complexes with all tested chiral carboxylates including amino acids and drug molecules with the enantioselectivity ranging from 1.1 to 3.2.

Unsubstituted Bambusurils: Post-Macrocyclization Modification of Versatile Intermediates

A new bambusuril derivative, (H)BU[6], lacking substituents on the ureidic nitrogen atoms, has been isolated and characterized. This macrocycle was prepared by the deprotection of bambusuril (PMB)BU[6]. (H)BU[6] is attractive for use as a starting compound for the preparation of other bambusuril derivatives, which was demonstrated via propargylation and the copper-catalyzed click reaction performed on the macrocycle.