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Centrohexaindane: six benzene rings mutually fixed in three dimensions - solid-state structure and six-fold

Dietmar Kuck1, Jens Linke2, Lisa Christin Teichmann2

  • 1Department of Chemistry, Bielefeld University, Universitätsstraße 25, 33615 Bielefeld, Germany. dietmar.kuck@uni-bielefeld.de and Center for Molecular Materials (CM2), Universitätsstraße 25, 33615 Bielefeld, Germany.

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Centrohexaindane, a unique 3D hydrocarbon, has its solid-state structure and molecular packing detailed. Six-fold nitration yields four isomers, indicating independent aromatic π-electron systems and enabling structural identification via NMR spectroscopy.

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Area of Science:

  • Organic Chemistry
  • Supramolecular Chemistry
  • Crystallography

Background:

  • Centrohexaindane is a unique hydrocarbon with six benzene rings around a neopentane core.
  • Understanding its solid-state structure and reactivity is crucial for developing novel molecular architectures.

Purpose of the Study:

  • To elucidate the solid-state molecular structure and packing of centrohexaindane.
  • To investigate the electrophilic aromatic substitution reactions of centrohexaindane, specifically nitration.
  • To characterize the resulting nitrofunctionalized derivatives.

Main Methods:

  • X-ray crystallography was used to determine the molecular structure and packing.
  • Electrophilic aromatic substitution (nitration) was performed on centrohexaindane and its congener, tribenzotriquinacene.
  • Nuclear Magnetic Resonance (NMR) spectroscopy was employed for structural identification of the isomers.

Main Results:

  • The Td-symmetry and precise orientation of centrohexaindane in the solid state were confirmed.
  • Six-fold nitration of centrohexaindane was achieved in high yield, producing four constitutional isomers.
  • The isomer distribution suggests independent electronic behavior of the six aromatic rings.

Conclusions:

  • The study provides a comprehensive understanding of centrohexaindane's solid-state properties and reactivity.
  • The conformational rigidity of centrohexaindane facilitates the structural elucidation of its complex derivatives.
  • This work opens avenues for designing novel functional materials based on this unique molecular scaffold.