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A Cucurbituril Derivative That Exhibits Cation-Modulated Self Assembly

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USTRNUL Lukáš BABIAK Michal KULHÁNEK Petr ŠINDELÁŘ Vladimír

Rok publikování 2016
Druh Článek v odborném periodiku
Časopis / Zdroj Journal of Organic Chemistry
Fakulta / Pracoviště MU

Přírodovědecká fakulta

Citace
www http://pubs.acs.org/doi/abs/10.1021/acs.joc.6b01288
Doi http://dx.doi.org/10.1021/acs.joc.6b01288
Obor Organická chemie
Klíčová slova SUPRAMOLECULAR CHEMISTRY; CUCURBITURIL; SELF-ASSOCIATION
Popis Cucurbiturils are the most potent artificial receptors known for many organic molecules in water. However, little is known about their supramolecular chemistry in organic solvents. Here we present a new cucurbituril derivative, 1, and investigate its supramolecular properties in methanol. The macrocycle resembles a five -membered cucurbituril in which four glycoluril units are replaced with propanediurea. Macrocyde 1 can bind to one cation such as potassium or anilinium via each of its opposed portals. The stability of these complexes in methanol at nanomolar concentrations exceeds that of complexes between metal cations and crown ethers. Moreover, macrocycle 1 forms a self -assembled tetrameric aggregate in the solid state and in methanol. The tetramer is stabilized by the addition of up to 1 equiv of a cation but is fully disassembled in the presence of 2 equiv of the cation. Cations can thus be used to tune the aggregation of 1 in solution.
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