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Title: | Two squares in a barrel: An axially disubstituted conformationally rigid aliphatic binding motif for cucurbit[6]uril | ||||||||||
Author: | Jelínková, Kristýna; Závodná, Aneta; Kaleta, Jiří; Janovský, Petr; Zatloukal, Filip; Nečas, Marek; Prucková, Zdeňka; Dastychová, Lenka; Rouchal, Michal; Vícha, Robert | ||||||||||
Document type: | Peer-reviewed article (English) | ||||||||||
Source document: | Journal of Organic Chemistry. 2023, vol. 88, issue 22, p. 15615-15625 | ||||||||||
ISSN: | 0022-3263 (Sherpa/RoMEO, JCR) | ||||||||||
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DOI: | https://doi.org/10.1021/acs.joc.3c01556 | ||||||||||
Abstract: | Novel binding motifs suitable for the construction of multitopic guest-based molecular devices (e.g., switches, sensors, data storage, and catalysts) are needed in supramolecular chemistry. No rigid, aliphatic binding motif that allows for axial disubstitution has been described for cucurbit[6]uril (CB6) so far. We prepared three model guests combining spiro[3.3]heptane and bicyclo[1.1.1]pentane centerpieces with imidazolium and ammonium termini. We described their binding properties toward CB6/7 and α-/β-CD using NMR, titration calorimetry, mass spectrometry, and single-crystal X-ray diffraction. We found that a bisimidazolio spiro[3.3]heptane guest forms inclusion complexes with CB6, CB7, and β-CD with respective association constants of 4.0 × 104, 1.2 × 1012, and 1.4 × 102. Due to less hindering terminal groups, the diammonio analogue forms more stable complexes with CB6 (K = 1.4 × 106) and CB7 (K = 3.8 × 1012). The bisimidazolio bicyclo[1.1.1]pentane guest forms a highly stable complex only with CB7 with a K value of 1.1 × 1011. The high selectivity of the new binding motifs implies promising potential in the construction of multitopic supramolecular components. | ||||||||||
Full text: | https://pubs.acs.org/doi/10.1021/acs.joc.3c01556 | ||||||||||
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