Issue 45, 2011
From the journal:

Dalton Transactions

Clipping and stoppering anion templated synthesis of a [2]rotaxanehost system†

Yitong Li,a   Kathleen M. Mullen,ac   João Sardinha,b   Vítor Félixb  and  Paul D. Beer*a  

* Corresponding authors

a Inorganic Chemistry Laboratory, Department of Chemistry, University of Oxford, South Parks Road, Oxford, UK
E-mail: paul.beer@chem.ox.ac.uk
Fax: (+44) 1865-272-690

b Departamento de Química, CICECO and Secção Autónoma de Ciências da Saúde Universidade de Aveiro, Aveiro, Portugal
E-mail: vitor.felix@ua.pt
Fax: (+351) 234 370084

c Current address: Chemistry, Faculty of Science and Technology, Queensland University of Technology, G. P. O. Box 2434, Brisbane, Australia
E-mail: kathleen.mullen@qut.edu.au
Fax: +61-7-3864-1804

Abstract

A new [2]rotaxane host system containing nitro-isophthalamide macrocycle and polyether functionalised pyridinium axle components is prepared via clipping and stoppering synthetic methodologies using chloride anion templation. After removing the chloride anion template, 1H NMR titration experiments reveal the unique interlocked host cavity to be highly selective for binding chloride and bromide in preference to basic oxoanions in competitive aqueous solvent mixtures. The rotaxane host system proved to be a superior anion complexant in comparison to the individual macrocycle and axle components. The anion binding affinity of the novel rotaxane is also investigated via molecular dynamics simulations and in general the structural data obtained corroborates the experimental solution anion recognition behaviour.

Graphical abstract: Clipping and stoppering anion templated synthesis of a [2]rotaxane host system

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Article information

DOI
https://doi.org/10.1039/C1DT10887E
Article type
Paper
Submitted
11 May 2011
Accepted
07 Jul 2011
First published
25 Aug 2011

Dalton Trans., 2011,40, 12180-12190

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Clipping and stoppering anion templated synthesis of a [2]rotaxane host system

Y. Li, K. M. Mullen, J. Sardinha, V. Félix and P. D. Beer, Dalton Trans., 2011, 40, 12180 DOI: 10.1039/C1DT10887E

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