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Issue 107, 2016, Issue in Progress
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An adamantane-based disubstituted binding motif with picomolar dissociation constants for cucurbit[n]urils in water and related quaternary assemblies

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Abstract

A non-axial centerpiece based on 1,3-disubstituted adamantane was designed, and three new guests were prepared. In the structure of the heterotritopic guests, the central adamantane site was combined with two terminal butyl or 1-adamantyl sites. The new central binding motif displayed an extraordinarily high affinity towards CB8 (Ka = (5.3 ± 0.3) × 1012 M−1 in water) to allow formation of quaternary assemblies with geometries which are dependent on the nature of macrocycles. Based on the individual binding strengths, the replacement of CB7 by CB8 led to inverse arrangements of the quaternary assemblies; i.e., β-CD is capped at the central site by two CB7 units, while the CB8 prefers the central site to be capped with two β-CD units.

Graphical abstract: An adamantane-based disubstituted binding motif with picomolar dissociation constants for cucurbit[n]urils in water and related quaternary assemblies

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Publication details

The article was received on 21 Sep 2016, accepted on 24 Oct 2016 and first published on 28 Oct 2016


Article type: Paper
DOI: 10.1039/C6RA23524G
Citation: RSC Adv., 2016,6, 105146-105153
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    An adamantane-based disubstituted binding motif with picomolar dissociation constants for cucurbit[n]urils in water and related quaternary assemblies

    E. Babjaková, P. Branná, M. Kuczyńska, M. Rouchal, Z. Prucková, L. Dastychová, J. Vícha and R. Vícha, RSC Adv., 2016, 6, 105146
    DOI: 10.1039/C6RA23524G

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