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A synthetic molecular pentafoil knot

DOI: 10.1038/nchem.1193 DOI Help
PMID: 22169866 PMID Help

Authors: Jean-françois Ayme (University of Edinburgh) , Jonathon E. Beves (University of Edinburgh) , David Leigh (University of Edinburgh) , Roy T. Mcburney (University of Edinburgh) , Kari Rissanen (University of Jyväskylä) , David Schultz (University of Edinburgh)
Co-authored by industrial partner: No

Type: Journal Paper
Journal: Nature Chemistry

State: Published (Approved)
Published: November 2011

Abstract: Knots are being discovered with increasing frequency in both biological and synthetic macromolecules and have been fundamental topological targets for chemical synthesis for the past two decades. Here, we report on the synthesis of the most complex non-DNA molecular knot prepared to date: the self-assembly of five bis-aldehyde and five bis-amine building blocks about five metal cations and one chloride anion to form a 160-atom-loop molecular pentafoil knot (five crossing points). The structure and topology of the knot is established by NMR spectroscopy, mass spectrometry and X-ray crystallography, revealing a symmetrical closed-loop double helicate with the chloride anion held at the centre of the pentafoil knot by ten CH center dot center dot center dot Cl- hydrogen bonds. The one-pot self-assembly reaction features an exceptional number of different design elements-some well precedented and others less well known within the context of directing the formation of (supra)molecular species. We anticipate that the strategies and tactics used here can be applied to the rational synthesis of other higher-order interlocked molecular architectures.

Subject Areas: Chemistry

Instruments: I19-Small Molecule Single Crystal Diffraction

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