Journal
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA
Volume 110, Issue 26, Pages 10531-10535Publisher
NATL ACAD SCIENCES
DOI: 10.1073/pnas.1302683110
Keywords
coordination chemistry; metal-organic capsules; self-assembly; supramolecular chemistry; stereochemistry
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Funding
- European Research Council
- Engineering and Physical Sciences Research Council [EP/I005447/1] Funding Source: researchfish
- EPSRC [EP/I005447/1] Funding Source: UKRI
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Here we describe the phenomenon of symmetry breaking within a series of M4L6 container molecules. These containers were synthesized using planar rigid bis-bidentate ligands based on 2,6-substituted naphthalene, anthracene, or anthraquinone spacers and FeII ions. The planarity of the ligand spacer favors a stereochemical configuration in which each cage contains two metal centers of opposite handedness to the other two, which would ordinarily result in an S-4-symmetric, achiral configuration. Reduction of symmetry from S-4 to C-1 is achieved by the spatial offset between each ligand's pair of binding sites, which breaks the S-4 symmetry axis. Using larger Cd-II or Co-II ions instead of Fe-II resulted, in some cases, in the observation of dynamic motion of the symmetry-breaking ligands in solution. NMR spectra of these dynamic complexes thus reflected apparent S-4 symmetry owing to rapid interconversion between energetically degenerate, enantiomeric C-1-symmetric conformations.
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