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

0578236 - ÚOCHB 2024 RIV US eng J - Článek v odborném periodiku
Jelínková, Kristýna - Závodná, A. - Kaleta, Jiří - Janovský, P. - Zatloukal, F. - Nečas, M. - Prucková, Z. - Dastychová, L. - Rouchal, M. - Vícha, R.
Two Squares in a Barrel: An Axially Disubstituted Conformationally Rigid Aliphatic Binding Motif for Cucurbit[6]uril.
Journal of Organic Chemistry. Roč. 88, č. 22 (2023), s. 15615-15625. ISSN 0022-3263. E-ISSN 1520-6904
Grant CEP: GA MŠMT(CZ) LUAUS23144
Výzkumná infrastruktura: CIISB III - 90242
Institucionální podpora: RVO:61388963
Klíčová slova: host-guest binding * affinity * movement
Obor OECD: Organic chemistry
Impakt faktor: 3.6, rok: 2022
Způsob publikování: Open access
https://doi.org/10.1021/acs.joc.3c01556

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.
Trvalý link: https://hdl.handle.net/11104/0347272


Vědecká data: CCDC, CCDC