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Controlling the Reactivity of the SeSe Bond by the Supramolecular Chemistry of Cucurbituril
Author(s) -
Ren Huifeng,
Huang Zehuan,
Yang Hui,
Xu Huaping,
Zhang Xi
Publication year - 2015
Publication title -
chemphyschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.016
H-Index - 140
eISSN - 1439-7641
pISSN - 1439-4235
DOI - 10.1002/cphc.201402840
Subject(s) - cucurbituril , supramolecular chemistry , chemistry , reactivity (psychology) , redox , photochemistry , combinatorial chemistry , organic chemistry , molecule , medicine , alternative medicine , pathology
We describe a new strategy to control the reactivity of SeSe bond by using supramolecular chemistry of cucurbituril. We have demonstrated that selenocystamine (SeCy) and cucurbit[6]uril (CB[6]) can form a stable supramolecular complex ( K a =5.5×10 6 M −1 ). Before complexation, the free SeSe bond in SeCy is rather sensitive to redox stimuli and gets disrupted quickly with addition of reductant or oxidant. However, after binding with CB[6], the SeSe bond becomes quite inert and hardly reacts with reductant or oxidant. One advantage of this supramolecular protection is that it can be applied in a wide pH range from weakly acidic to basic. Additionally, the supramolecular complex formed by SeCy and CB[6] can be reversibly dissociated simply with addition of Ba 2+ .