Cooperative Binding of Cucurbit[n]urils and beta-Cyclodextrin to Heteroditopic Imidazolium-Based Guests

作者：Branna Petra; Cernochova Jarmila; Rouchal Michal; Kulhanek Petr; Babinsky Martin; Marek Radek; Necas Marek; Kuritka Ivo; Vicha Robert^*

来源：Journal of Organic Chemistry, 2016, 81(20): 9595-9604.

DOI：10.1021/acs.joc.6b01564

Imidazolium-based guests containing two distinct binding epitopes are capable of binding beta-cyclodextrin and cucurbit[6/7]uril (CB) simultaneously to form heteroternary 1:1:1 inclusion complexes. In the final 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.

• 出版日期2016-10-21