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Electrocyclic reactions, cycloadditions, and sigmatropic rearrangements are concerted pericyclic reactions that proceed via a cyclic transition state. These reactions are stereospecific and regioselective. The stereochemistry of the products depends on the symmetry characteristics of the interacting orbitals and the reaction conditions. Accordingly, pericyclic reactions are classified as either symmetry-allowed or symmetry-forbidden. Woodward and Hoffmann presented the selection criteria for...
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Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
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Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
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The chair conformation is the most stable form of cyclohexane due to the absence of angle and torsional strain. The absence of angle strain is a result of cyclohexane’s bond angle being very close to the ideal tetrahedral bond angle of 109.5° in its chair conformer. Similarly, the torsional strain is also absent owing to the perfectly staggered arrangement of bonds.
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Cucurbit[8]uril-mediated pseudo[2,3]rotaxanes.

Guanglu Wu1, István Szabó2, Edina Rosta2

  • 1Melville Laboratory for Polymer Synthesis, Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW, UK. oas23@cam.ac.uk.

Chemical Communications (Cambridge, England)
|October 22, 2019
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Summary

Researchers created pseudo[2,3]rotaxanes using cucurbit[8]uril (CB[8]) macrocycles and viologen derivatives. Adding a third CB[8] macrocycle precisely aligns chromophores, enabling electron delocalization along the molecular axis.

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Area of Science:

  • Supramolecular Chemistry
  • Materials Science

Background:

  • Pseudo[2,3]rotaxanes are supramolecular architectures formed by macrocycle complexation.
  • Extended viologen derivatives serve as suitable guest molecules for macrocyclic hosts.

Purpose of the Study:

  • To fabricate pseudo[2,3]rotaxanes using cucurbit[8]uril (CB[8]) and extended viologen derivatives.
  • To explore the structural implications of incorporating a third CB[8] macrocycle onto pseudo[2,2]rotaxanes.
  • To investigate the resulting electronic properties, specifically electron delocalization.

Main Methods:

  • Complexation of cucurbit[8]uril (CB[8]) macrocycles with extended viologen derivatives.
  • Application of two specific design rules for incorporating a third CB[8] macrocycle.
  • Structural analysis to confirm the alignment of chromophores.

Main Results:

  • Successful fabrication of pseudo[2,3]rotaxanes.
  • Demonstration of design rules for incorporating a third CB[8] macrocycle.
  • Confinement of dimeric chromophore stacking into specific alignment.
  • Observation of effective electron delocalization along the molecular axis.

Conclusions:

  • Pseudo[2,3]rotaxanes can be effectively synthesized via CB[8]-viologen complexation.
  • The incorporation of a third CB[8] macrocycle provides precise control over molecular assembly.
  • Controlled alignment facilitates enhanced electron delocalization, opening avenues for advanced molecular materials.