Selective recognition of small hydrogen bond acceptors by a calix[6]arene-based molecular container

ABSTRACT

Selective molecular recognition is of primary importance for applications such as sensing and separation of chemicals. This work describes the host-guest and crystallisation properties of a penta-carbamated calix[6]arene designed as a molecular container with a H-donating recognition group directed towards the heart of the cavity. As demonstrated by NMR spectroscopy and X-ray diffraction studies, this macrocyclic receptor can selectively recognise small H-bond acceptors through one or two hydrogen bonds, the guests nesting inside the polyaromatic cavity surrounded by eleven bulky tert-butyl groups.

Graphical Abstract

KEYWORDS:

• Calixarenes
• host-guest
• inclusion complexes
• molecular recognition
• macrocycles

Acknowledgments

This work was supported by the Université libre de Bruxelles (ULB) and the Fonds pour la Formation à la Recherche dans l’Industrie et dans l’Agriculture (FRIA). The crystallographic study benefited from equipment available at UNamur as part of the “Plateforme de Caractérisation PC2” and from valuable technical support of Mrs B. Norberg. We thank Diamond Light Source for time on Beamline I19 (CY21497).

Disclosure statement

No potential conflict of interest was reported by the authors.

Data availability

The crystal structures of 2 and 2⊃DMSO are available at the Cambridge Crystallographic Data Centre: CCDC 1959492 and 1952601.

Supplementary material

Supplemental data for this article can be accessed here.

Additional information

Funding

This work was supported by the Fonds pour la Formation à la Recherche dans l’Industrie et dans l’Agriculture.