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Related Experiment Videos

Embracing C(60) with multiarmed geodesic partners.

S Mizyed1, P E Georghiou, M Bancu

  • 1Department of Chemistry, Memorial University of Newfoundland, St. John's, Newfoundland, Canada A1B 3X7.

Journal of the American Chemical Society
|December 26, 2001
PubMed
Summary
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Novel bowl-shaped corannulene derivatives were synthesized and found to form complexes with C(60) fullerenes. These host-guest complexes exhibit varying binding strengths, indicating potential applications in molecular recognition and supramolecular chemistry.

Area of Science:

  • Supramolecular Chemistry
  • Organic Synthesis
  • Materials Science

Background:

  • Corannulene, a unique curved polycyclic aromatic hydrocarbon, serves as a versatile platform for constructing host molecules.
  • Functionalized corannulenes with thioether linkages offer tailored electronic and steric properties for molecular recognition.

Purpose of the Study:

  • To synthesize novel pentakis- and tetrakis-substituted thiophenyl corannulene derivatives.
  • To investigate the host-guest complexation behavior of these corannulenes with C(60) fullerenes.

Main Methods:

  • Synthesis via chlorination of corannulene followed by nucleophilic aromatic substitution with sodium thiophenolates.
  • Characterization using spectroscopic techniques.
  • Binding studies employing (1)H NMR titration in toluene-d(8).

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Main Results:

  • Successful synthesis of 1,3,5,7,9-pentakis(4-methoxyphenylthio)corannulene, 1,3,5,7,9-pentakis(2-naphthylthio)corannulene, and 1,3,6,8-tetrakis(4-methoxyphenylthio)corannulene.
  • Demonstration of 1:1 complex formation between the synthesized corannulenes and C(60) fullerenes.
  • Quantification of association constants (454, 368, and 280 M(-1)) for the respective complexes.

Conclusions:

  • The synthesized corannulene derivatives act as effective hosts for C(60) fullerenes.
  • The binding affinity is influenced by the nature and position of the thiophenyl substituents.
  • These findings highlight the potential of functionalized corannulenes in fullerene encapsulation and separation.