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Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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Selective surface decoration of corannulene.

Alexander V Zabula1, Cristina Dubceac, Alexander S Filatov

  • 1Department of Chemistry, University at Albany, State University of New York, 1400 Washington Avenue, Albany, New York 12222, USA.

The Journal of Organic Chemistry
|October 28, 2011
PubMed
Summary

This study details the synthesis of novel nonplanar carbocations derived from corannulene, functionalized with haloalkyl chains. These carbocations undergo further reactions, leading to decorated polyarenes with intramolecular hydrogen bonds.

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Area of Science:

  • Organic Chemistry
  • Supramolecular Chemistry
  • Materials Science

Background:

  • Corannulene is a nonplanar polycyclic aromatic hydrocarbon with a unique bowl shape.
  • Functionalization of corannulene is key to developing novel materials and understanding its chemical properties.

Purpose of the Study:

  • To synthesize and characterize novel nonplanar carbocations from corannulene.
  • To investigate the selective functionalization of corannulene derivatives.
  • To explore the subsequent reactions and structural features of these decorated polyarenes.

Main Methods:

  • Reaction of corannulene with 1,2-dihaloethanes in the presence of aluminum chloride (AlCl(3)).
  • Single-crystal X-ray diffraction for structural elucidation of carbocation salts.
  • Nuclear Magnetic Resonance (NMR) spectroscopy for product characterization.

Main Results:

  • Stable nonplanar carbocations C(20)H(10)CH(2)CH(2)Hal(+) were synthesized.
  • Selective abstraction of chloride over bromide was observed with 1-bromo-2-chloroethane.
  • X-ray diffraction confirmed the bowl-shaped structures of carbocations 1 and 2.
  • Further functionalization with alkoxy groups and observation of intramolecular hydrogen bonds (H···O and H···Br) in products 3 and 4.

Conclusions:

  • The synthesis of stable, nonplanar carbocations from corannulene is achievable.
  • Selective functionalization strategies for corannulene derivatives were demonstrated.
  • The resulting decorated polyarenes exhibit interesting structural features, including intramolecular hydrogen bonding.