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Issue 92, 2019
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Unveiling the formation 1 : 2 supramolecular complexes between cucurbit[7]uril and a cationic calix[4]arene derivative

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Abstract

The formation of host–guest complexes between cucurbit[7]uril (CB7) and a tetracationic calix[4]arene derivative in the so-called cone conformation was investigated by 1H NMR, DOSY NMR, isothermal titration calorimetry and ESI-MS. The results point to the formation of 1 : 1, 1 : 2 and 2 : 1 CB7 : calixarene complexes with binding constants of 3 × 106 M−1, ≈2 × 102 M−1, and 9 × 104 M−1 respectively. The study demonstrates, on one hand, that despite having four potential recognition sites, the calixarene only binds two CB7 molecules and, on the other, that for sterically crowded binding motifs that prevent CB7 inclusion with optimized hydrophobic and ion–dipole interactions, the formation of 1 : 2 complexes can be observed most likely due to formation of external binding of the cationic moieties to the CB7 carbonyl portals.

Graphical abstract: Unveiling the formation 1 : 2 supramolecular complexes between cucurbit[7]uril and a cationic calix[4]arene derivative

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Supplementary files

Article information


Submitted
17 Sep 2019
Accepted
17 Oct 2019
First published
21 Oct 2019

Chem. Commun., 2019,55, 13828-13831
Article type
Communication

Unveiling the formation 1 : 2 supramolecular complexes between cucurbit[7]uril and a cationic calix[4]arene derivative

M. Pessêgo, J. Mendoza, J. P. da Silva, N. Basílio and L. Garcia-Rio, Chem. Commun., 2019, 55, 13828
DOI: 10.1039/C9CC07280B

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