Cooperative binding of cucurbit[n]urils and beta-cyclodextrin to heteroditopic imidazolium-based guests
| Authors | |
|---|---|
| Year of publication | 2016 |
| Type | Article in Periodical |
| Magazine / Source | The Journal of Organic Chemistry |
| MU Faculty or unit | |
| Citation | |
| Web | DOI: 10.1021/acs.joc.6b01564 |
| Doi | http://dx.doi.org/10.1021/acs.joc.6b01564 |
| Field | Organic chemistry |
| Keywords | macrocycle; cyclodextrin; cucurbit[n]uril; NMR; binding; cooperativity |
| Attached files | |
| Description | Imidazolium-based guests containing two distinct binding epitopes are capable of binding beta-cyclodextrin and cucurbit[6/7]uril (CB) simultaneously to form hetero-ternary 1:1:1 inclusion complexes. In the final configuration, the hosts occupy binding sites disfavored in the binary complexes because of the chemically induced reorganization of the intermediate 1:1 aggregate. In addition, the reported guests are capable of binding two CBs to form either 1:2 or 1:1:1 ternary assemblies despite consisting of a single cationic moiety. Whereas the adamantane site binds CB solely via hydrophobic interactions, the CB unit at the butyl site is stabilized by a combination of hydrophobic and ion-dipole interactions. |
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