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Uptake of Hydrocarbons in Aqueous Solution by Encapsulation in Acyclic Cucurbit[ n ]uril‐Type Molecular Containers
Author(s) -
Lu Xiaoyong,
Isaacs Lyle
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201602671
Subject(s) - naphthalene , aqueous solution , chemistry , solubility , benzene , hydrocarbon , organic chemistry
The ability of two water‐soluble acyclic cucurbit[ n ]uril (CB[ n ]) type containers, whose hydrophobic cavity is defined by a glycoluril tetramer backbone and terminal aromatic (benzene, naphthalene) sidewalls, to act as solubilizing agents for hydrocarbons in water is described. 1 H NMR spectroscopy studies and phase‐solubility diagrams establish that the naphthalene‐walled container performs as well as, or better than, CB[7] and CB[8] in promoting the uptake of poorly soluble hydrocarbons into aqueous solution through formation of host–hydrocarbon complexes. The naphthalene‐walled acyclic CB[ n ] container is able to extract large hydrocarbons from crude oil into aqueous solution.