A synthetic molecular pentafoil knot

Jean François Ayme, Jonathon E. Beves, David A. Leigh*, Roy T. McBurney, Kari Rissanen, David Schultz

*Corresponding author for this work

Research output: Contribution to journalArticle

269 Citations (Scopus)

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⋯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.

Original languageEnglish
Pages (from-to)15-20
Number of pages6
JournalNature Chemistry
Volume4
Issue number1
DOIs
Publication statusPublished - Jan 2012
Externally publishedYes

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