Propanediurea-Based Molecular Clips Bind Halide Anions: An Insight into the Mechanism of Cucurbituril Formation

Vladimir Sindelar, Marek Necas, Tomas Lizal & Lukas Ustrnul
The synthesis and supramolecular properties of the first methylene-bridged propanediurea-based dimers are described. These dimers, bearing an aromatic sidewall, have the shape of molecular clips. Unlike glycoluril-based dimers, these clips neither dimerize nor accept any organic guests, due to their small cavities. Both propanediurea- and glycoluril-based dimers bind halide anions on the convex side of the molecules, even in highly polar organic solvents. This observation brings new insights into the mechanism of cucurbituril formation.
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