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

Roy Lavendomme; Florent Desroches; Steven Moerkerke; Filip Topić; Johan Wouters; Kari Rissanen; Michel Luhmer; Ivan Jabin

doi:10.1080/10610278.2019.1679374

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

Roy Lavendomme, Florent Desroches, Steven Moerkerke, Filip Topić, Johan Wouters, Kari Rissanen, Michel Luhmer, Ivan Jabin

Unit of theoretical and structural physico-chemistry

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	23-29
Number of pages	7
Journal	Supramolecular Chemistry
Volume	32
Issue number	1
DOIs	https://doi.org/10.1080/10610278.2019.1679374
Publication status	Published - 2 Jan 2020

Keywords

Calixarenes
host-guest
inclusion complexes
macrocycles
molecular recognition

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10.1080/10610278.2019.1679374

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Physical Chemistry and characterization(PC2)
Johan Wouters (Manager) & Carmela Aprile (Manager)
Technological Platform Physical Chemistry and characterization
Facility/equipment: Technological Platform

CCDC 1959492: Experimental Crystal Structure Determination
Lavendomme, R. (Creator), Desroches, F. (Creator), Moerkerke, S. (Creator), Topić, F. (Creator), Wouters, J. (Contributor), Rissanen, K. (Creator), Luhmer, M. (Creator) & Jabin, I. (Creator), University of Namur, 2 Jan 2020
DOI: 10.5517/ccdc.csd.cc23s0fc, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc23s0fc&sid=DataCite
Dataset
CCDC 1952601: Experimental Crystal Structure Determination
Lavendomme, R. (Creator), Desroches, F. (Creator), Moerkerke, S. (Creator), Topić, F. (Creator), Wouters, J. (Contributor), Rissanen, K. (Creator), Luhmer, M. (Creator) & Jabin, I. (Creator), University of Namur, 2 Jan 2020
DOI: 10.5517/ccdc.csd.cc23jv4n, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc23jv4n&sid=DataCite
Dataset

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@article{18820df364454ce09babae577f384d37,

title = "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.",

keywords = "Calixarenes, host-guest, inclusion complexes, macrocycles, molecular recognition",

author = "Roy Lavendomme and Florent Desroches and Steven Moerkerke and Filip Topi{\'c} and Johan Wouters and Kari Rissanen and Michel Luhmer and Ivan Jabin",

note = "Funding Information: This work was supported by the Universit{\'e} libre de Bruxelles (ULB) and the Fonds pour la Formation {\`a} la Recherche dans l{\textquoteright}Industrie et dans l{\textquoteright}Agriculture (FRIA). The crystallographic study benefited from equipment available at UNamur as part of the “Plateforme de Caract{\'e}risation PC2” and from valuable technical support of Mrs B. Norberg. We thank Diamond Light Source for time on Beamline I19 (CY21497). Funding Information: This work was supported by the Fonds pour la Formation ? la Recherche dans l?Industrie et dans l?Agriculture?. This work was supported by the Universit? libre de Bruxelles (ULB) and the Fonds pour la Formation ? 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 Caract?risation PC2? and from valuable technical support of Mrs B. Norberg. We thank Diamond Light Source for time on Beamline I19 (CY21497). Publisher Copyright: {\textcopyright} 2019, {\textcopyright} 2019 Informa UK Limited, trading as Taylor & Francis Group.",

year = "2020",

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doi = "10.1080/10610278.2019.1679374",

language = "English",

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Selective recognition of small hydrogen bond acceptors by a calix[6]arene-based molecular container. / Lavendomme, Roy; Desroches, Florent; Moerkerke, Steven; Topić, Filip; Wouters, Johan; Rissanen, Kari; Luhmer, Michel; Jabin, Ivan.

In: Supramolecular Chemistry, Vol. 32, No. 1, 02.01.2020, p. 23-29.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

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AU - Desroches, Florent

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AU - Rissanen, Kari

AU - Luhmer, Michel

AU - Jabin, Ivan

N1 - Funding Information: 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). Funding Information: This work was supported by the Fonds pour la Formation ? la Recherche dans l?Industrie et dans l?Agriculture?. This work was supported by the Universit? libre de Bruxelles (ULB) and the Fonds pour la Formation ? 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 Caract?risation PC2? and from valuable technical support of Mrs B. Norberg. We thank Diamond Light Source for time on Beamline I19 (CY21497). Publisher Copyright: © 2019, © 2019 Informa UK Limited, trading as Taylor & Francis Group.

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N2 - 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.

AB - 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.

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KW - inclusion complexes

KW - macrocycles

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JO - Supramolecular Chemistry

JF - Supramolecular Chemistry

SN - 1061-0278

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

Abstract

Keywords

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Physical Chemistry and characterization(PC2)

CCDC 1959492: Experimental Crystal Structure Determination

CCDC 1952601: Experimental Crystal Structure Determination

Cite this