Cubane, an intriguing chemical curiosity first studied in the early 1960s, has become a valuable structural motif and has recently been involved in the structures of a great number of prospective compounds. The first dicationic supramolecular guest 5 is prepared and derived from a 1,4-disubstituted cubane moiety, and its binding behavior toward cucurbit[n]urils (CBn) and cyclodextrins (CD) is studied. The bisimidazolium salt 5 forms 1:1 inclusion complexes with CB7, CB8, and β-CD with the respective association constants (6.7 ± 0.5) × 1011 M-1, (1.5 ± 0.2) × 109 M-1, and <102 M-1 in water. The solid-state structures of the 5@CB7 and 5@CB8 complexes are also reported.

Department of Chemistry Faculty of Science Masaryk University Kamenice 5 625 00 Brno Czech Republic

Department of Chemistry Faculty of Technology Tomas Bata University in Zlín Vavrečkova 275 760 01 Zlín Czech Republic

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Chlorinated Cubane-1,4-dicarboxylic Acids

Two Squares in a Barrel: An Axially Disubstituted Conformationally Rigid Aliphatic Binding Motif for Cucurbit[6]uril