Abstract
Cucurbiturils (CB) with seven and eight glycoluril units form inclusion complexes with 1-butyl-3-methylimidazolium tetrafluoroborate (bmimBF 4). These complexes have been characterized by the chemical shift changes in the 1H NMR and by the ESI-MS peaks. Due to complex formation, solubility of CB[7] and CB[8] in bmimBF 4 is remarkably high (up to one order of magnitude higher than in water). In contrast, no evidence for complex formation was obtained in the case of CB[5] and CB[6]. Molecular modelling has provided a justification of these facts based on the relative molecular size of bmim + and the corresponding dimensions of the CB capsule. Addition of minor quantities of CB[7] and CB[8] to bmimBF4 (in the order of 1–1000 molar ratio) is able to produce a remarkable influence on the viscosity of the ionic liquid. Also, the presence of low amounts of CB plays a strong influence on the performance of bmimBF 4 as reaction medium for the Knoevenagel condensation of benzaldehyde and diethyl malonate catalyzed by NaOH. The results exemplify the potential of applying supramolecular chemistry to derive a generation of advanced ionic liquids specially tuned for a catalytic reaction.
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