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pH Control on the Sequential Uptake and Release of Organic Cations by Cucurbit[7]uril
Author(s) -
Mikulu Lukas,
Michalicova Romana,
Iglesias Vivian,
Yawer Mirza A.,
Kaifer Angel E.,
Lubal Premysl,
Sindelar Vladimir
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201604417
Subject(s) - supramolecular chemistry , dissociation (chemistry) , chemistry , cucurbituril , combinatorial chemistry , ferrocene , stereochemistry , molecule , organic chemistry , electrochemistry , electrode
Cucurbit[7]uril (CB7) is a macrocycle with the ability to form the most stable supramolecular complexes in water ever reported for an artificial receptor. Its use for the design of advanced functional materials is, however, very limited because there is no example of a fully reversible CB7 based supramolecular complex enabling repetitious dissociation/association controlled by external stimuli. We report the synthesis of a new ferrocene amino acid that forms with CB7 a 1:1 inclusion complex that is stable in submicromolar concentration at low pH but dissociates at high pH. This reversible process was used for the sequential uptake and release of bispyridinium and antraquinone guests by CB7, which is controlled by adjusting the pH of the solution.