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Issue 11, 2014
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Active-template synthesis of “click” [2]rotaxane ligands: self-assembly of mechanically interlocked metallo-supramolecular dimers, macrocycles and oligomers

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Abstract

Due to potential applications in the biological and material sciences there is considerable interest in the development of mechanically interlocked ligands (MILs). The mild functional-group tolerant copper(I)-catalysed azide–alkyne cycloaddition active-metal-template (CuAAC-AMT) method has been exploited to generate mono- and bi-functionalised [2]rotaxanes by interlocking an exo-alcohol functionalised macrocycle and functionalised triphenylmethyl stoppers. These [2]rotaxanes were post-synthetically conjugated to either one or two 2,2′,6′,2′′-terpyridine (terpy) coordinating units to generate mechanically interlocked “super” ligands. Addition of Fe(II) ions to the mono-terpy ligand leads to the formation of a metallo-bis-([2]rotaxane). At high dilution the bi-terpy [2]rotaxane ligand forms a [2]rotaxane metallo-macrocycle, in the presence of Fe(II) ions. Conversely, at high concentration self-assembly of the bi-terpy [2]rotaxane ligand with Fe(II) ions results in the generation of a metallo-supramolecular poly-[2]rotaxane oligomer. The [2]rotaxane ligands and corresponding Fe(II) complexes have been characterised with 1H and 13C NMR and UV-vis spectroscopies, high resolution electrospray ionisation mass spectrometry (HR-ESMS), and elemental analyses. Additionally, 1H DOSY NMR spectroscopy and GPC analysis were used to provide evidence for the constitution of the self-assembled metallo-supramolecular mechanically-interlocked architectures.

Graphical abstract: Active-template synthesis of “click” [2]rotaxane ligands: self-assembly of mechanically interlocked metallo-supramolecular dimers, macrocycles and oligomers

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Article information


Submitted
16 May 2014
Accepted
04 Jul 2014
First published
04 Jul 2014

Chem. Sci., 2014,5, 4283-4290
Article type
Edge Article
Author version available

Active-template synthesis of “click” [2]rotaxane ligands: self-assembly of mechanically interlocked metallo-supramolecular dimers, macrocycles and oligomers

A. Noor, S. C. Moratti and J. D. Crowley, Chem. Sci., 2014, 5, 4283
DOI: 10.1039/C4SC01438C

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