The dicyanoaurate anion plays a central role in the gold mining industry. Its recovery from an aqueous solution is dominantly achieved using activated carbon, which, however, suffers from several drawbacks. Herein, we report a simple preparation of a new material containing the bambusuril macrocycle physically sorbed on the surface of silica gel particles. We utilized the ability of bambusuril to form a unique material that extracts dicyanoaurate from an aqueous solution via supramolecular host-guest interactions. Notably, the material selectively removed dicyanoaurate over dicyanoargentate. Equilibrium sorption and desorption of the anion were achieved within minutes at ambient temperature, significantly outperforming activated carbon.

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Bambus[6]urils and biotin[6]urils are macrocycles with an exceptional affinity for inorganic anions. Here, we investigated statistical condensation of 2,4-dibenzylglycoluril and d-biotin, monomers of the corresponding macrocycles, to prepare the enantiomerically pure macrocycle 1 containing a single d-biotin and five glycoluril units. Host-guest properties of 1 in chloroform solution and solid state were investigated. The macrocycle 1 bearing a single functional group was employed in the formation of [1]rotaxane utilizing reversible covalent bonds.

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A general strategy for the synthesis of 2N,4N'-disubstituted glycoluril enantiomers on a multigram scale using orthogonal protection is reported. The use of these glycolurils is demonstrated in the synthesis of enantiomerically pure bambus[6]uril macrocycles. Moreover, the deprotection of (S)-1-phenylethyl substituents on the macrocycle was achieved, opening access to various chiral bambus[6]urils via post-macrocyclization modification strategy.

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