A Star of David catenane

We describe the synthesis of a [2]catenane that consists of two triply entwined 114-membered rings, a molecular link. The woven scaffold is a hexameric circular helicate generated by the assembly of six tris(bipyridine) ligands with six iron( II ) cations, with the size of the helicate promoted by t...

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Bibliographic Details
Published in:Nature chemistry 2014-11, Vol.6 (11), p.978-982
Main Authors: Leigh, David A., Pritchard, Robin G., Stephens, Alexander J.
Format: Article
Language:English
Subjects:
639/638/541/964
Analytical Chemistry
Biochemistry
Cations
Chemistry
Chemistry/Food Science
Crystallography
Inorganic Chemistry
Ions
Iron
Ligands
Mass spectrometry
Organic Chemistry
Physical Chemistry
Scientific imaging
Spectroscopy
Sulfates
Topology
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Summary:We describe the synthesis of a [2]catenane that consists of two triply entwined 114-membered rings, a molecular link. The woven scaffold is a hexameric circular helicate generated by the assembly of six tris(bipyridine) ligands with six iron( II ) cations, with the size of the helicate promoted by the use of sulfate counterions. The structure of the ligand extension directs subsequent covalent capture of the catenane by ring-closing olefin metathesis. Confirmation of the Star of David topology (two rings, six crossings) is provided by NMR spectroscopy, mass spectrometry and X-ray crystallography. Extraction of the iron( II ) ions with tetrasodium ethylenediaminetetraacetate affords the wholly organic molecular link. The self-assembly of interwoven circular frameworks of controlled size, and their subsequent closure by multiple directed covalent bond-forming reactions, provides a powerful strategy for the synthesis of molecular topologies of ever-increasing complexity. The Star of David topology is an iconic symbol that has been used in religious and cultural contexts for thousands of years. Now it is assembled in molecular form through a hexameric circular helicate generated by six tris(bipyridine) ligands entwined about six iron( II ) cations. The structure of the two triply-entwined 114-membered rings is revealed by X-ray crystallography.
ISSN:1755-4330
1755-4349
DOI:10.1038/nchem.2056