Organic Letters
Organic Letters
5 years ago

Cubane Arrives on the Cucurbituril Scene

Cubane Arrives on the Cucurbituril Scene
Zdeňka Prucková, Heda Surmová, Lenka Dastychová, Marek Nečas, Kristýna Jelínková, Alena Matelová, Michal Rouchal, Robert Vícha
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01029

DOI: 10.1021/acs.orglett.7b01029

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