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Controlling the shape and chirality of an eight-crossing molecular knot

Research output: Contribution to journalArticlepeer-review

John P. Carpenter, Charlie T. McTernan, Jake L. Greenfield, Roy Lavendomme, Tanya K. Ronson, Jonathan R. Nitschke

Original languageEnglish
Pages (from-to)1534-1543
Number of pages10
JournalChem
Volume7
Issue number6
DOIs
Accepted/In press2021
Published10 Jun 2021

Bibliographical note

Funding Information: This work was supported by the European Research Council (695009), the UK Engineering and Physical Sciences Research Council ( EPSRC EP /P027067/1), networking contributions from the COST Action CA17139 EUTOPIA, and a Marie Curie Fellowship for J.P.C. (ITN-2010-264645). C.T.M. thanks the Leverhulme (ECF-2018-684) and Isaac Newton Trusts and Sidney Sussex College, Cambridge for Fellowship support. The authors thank the Department of Chemistry NMR Facility, University of Cambridge for performing some NMR experiments, the EPSRC UK National Mass Spectrometry Facility at Swansea University and the Department of Chemistry Mass Spectrometry Facility, University of Cambridge, for carrying out high resolution mass spectrometry, and Diamond Light Source (UK) for synchrotron beamtime on I19 (MT15768). Funding Information: This work was supported by the European Research Council (695009), the UK Engineering and Physical Sciences Research Council (EPSRC EP/P027067/1), networking contributions from the COST Action CA17139 EUTOPIA, and a Marie Curie Fellowship for J.P.C. (ITN-2010-264645). C.T.M. thanks the Leverhulme (ECF-2018-684) and Isaac Newton Trusts and Sidney Sussex College, Cambridge for Fellowship support. The authors thank the Department of Chemistry NMR Facility, University of Cambridge for performing some NMR experiments, the EPSRC UK National Mass Spectrometry Facility at Swansea University and the Department of Chemistry Mass Spectrometry Facility, University of Cambridge, for carrying out high resolution mass spectrometry, and Diamond Light Source (UK) for synchrotron beamtime on I19 (MT15768). J.P.C. and J.R.N. conceived the project. J.P.C. C.T.M. J.L.G. and R.L. performed the experiments and analyzed the data. T.K.R. collected the X-ray data and refined the structures. C.T.M. and J.P.C. drafted the manuscript. All authors discussed the results and edited the manuscript. The authors declare no competing interests. Publisher Copyright: © 2021 Elsevier Inc. Copyright: Copyright 2021 Elsevier B.V., All rights reserved.

King's Authors

Abstract

The knotting of biomolecules impacts their function and enables them to carry out new tasks. Likewise, complex topologies underpin the operation of many synthetic molecular machines. The ability to generate and control more complex architectures is essential to endow these machines with more advanced functions. Here, we report the synthesis of a molecular knot with eight crossing points, consisting of a single organic loop woven about six templating metal centers, via one-pot self-assembly from a pair of simple dialdehyde and diamine subcomponents and a single metal salt. The structure and topology of the knot were established by NMR spectroscopy, mass spectrometry, and X-ray crystallography. Upon demetallation, the purely organic strand relaxes into a symmetric conformation, while retaining the topology of the original knot. This knot is topologically chiral and may be synthesized diastereoselectively through the use of an enantiopure diamine building block.

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