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Multiple C-H Bond Activations in Corannulene by a Dirhenium Complex.

Richard D Adams1, Poonam Dhull1, Matthew Pennachio2

  • 1Department of Chemistry and Biochemistry, University of South Carolina, Columbia, SC, 29208, USA.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|February 19, 2019
PubMed
Summary

This study details the synthesis of novel rhenium-metalated corannulene compounds. Researchers achieved single and double metalation of corannulene using a rhenium precursor, forming unique organometallic structures.

Keywords:
C−H activationcorannulenemetalationoxidative additionrhenium

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Area of Science:

  • Organometallic Chemistry
  • Materials Science
  • Supramolecular Chemistry

Background:

  • Corannulene, a nonplanar polycyclic aromatic hydrocarbon, presents unique reactivity due to its curved structure.
  • Rhenium carbonyl complexes are known for their catalytic and synthetic applications.
  • Understanding C-H bond activation on polycyclic aromatic hydrocarbons is crucial for developing new materials and catalysts.

Purpose of the Study:

  • To investigate the reaction of a specific rhenium precursor with corannulene.
  • To synthesize and characterize novel metalated corannulene derivatives.
  • To explore the possibility of multiple C-H bond activations and the formation of di-metalated products.

Main Methods:

  • Reaction of Re2(CO)8(μ-C6H5)(μ-H) with corannulene.
  • Isolation and purification of reaction products.
  • Structural characterization using single crystal X-ray diffraction analysis.

Main Results:

  • Successful synthesis of a mono-metalated corannulene product, Re2(CO)8(μ-H)(μ-η2-1,2-C20H9), in 65% yield.
  • Formation of three distinct di-metalated corannulene isomers (compounds 3, 4, and 5) via a second C-H activation event.
  • Structural elucidation revealing bridging η2-σ+π coordination of the corannulenyl ligand and varying orientations of the rhenium groups in di-metalated products.

Conclusions:

  • The rhenium precursor readily undergoes oxidative addition to corannulene's C-H bonds, leading to metalation.
  • Corannulene can accommodate multiple rhenium metal centers, forming complex di-metalated structures.
  • The study demonstrates a new route to functionalized corannulene derivatives with potential applications in catalysis and materials science.