New macrocyclic derivatives of glycolurils, and method of preparing and using the same

Field: Macromolecular chemistry | Material chemistry | Organic chemistry


The present invention covers a new class of macrocyclic compounds which was named bambus[n]urils (wherein n is ranging from 4 to 24), wherein glycerol is a bicyclic molecule capable of binding other substances by non-covalent bonds. Due to the flexible structure bambus[n]urils are able to form a cycle containing only four glycoluril units (n = 4) and can adapt to the shape of a substance interacting with it. Bambus[n]urils have shown good solubility in organic solvents including chloroform, methanol, dimethylsulfoxide or mixtures of these solvents, but they are also dissolved in water in the presence of specific ions. The solubility of bambus[n]urils can be further influenced by a type of substitution. Bambus[n]urils can be easily modified, for example by introducing bulky substituents and significantly influencing their properties due to a conformational change of the macrocycle. It is also possible to introduce a suitable functional group on the macrocycle to allow it to be attached to silica, polymer or metal surface.

Commercial opportunity 

Bambos[n]urils can be used, for example, in water purification, removal of dissolved compounds from solutions, separations of gas or organic vapor mixtures. For their ability to selectively bind some anions and cations bambus[n]urils can be used as an ion-exchange material. Bambus[n]urils can be also used for the preparation of sensors for anion and cation detection and for the extraction, transportation, and regulation of anions. Because of the ability to bind various compounds, bambus[n]urils may be used for drug transportation and targeting in organisms, or in the food and pharmaceutical industry as a matrix bearing aromatic or curative compounds.

Their further advantage is easy preparation - the starting compounds and the solvents used are cheap and well-available. For this reason, scientists continue to investigate bambos[n]urils for the preparation of anion sensors, ion-selective electrodes, and other applications.

IP protection status

Granted patents in the Czech Republic, US, and Europe

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