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Synthesis and Structures of Polyphenylphenanthrenes.

Yonglong Xiao1, Joel T Mague1, James P Donahue1

  • 1Department of Chemistry, Tulane University, New Orleans, LA, 70118, USA.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|May 8, 2020
PubMed
Summary

Synthesizing octaphenylphenanthrene and decaphenylphenanthrene yielded highly twisted structures. Decaphenylphenanthrene is configurationally unstable at room temperature due to its low racemization barrier.

Keywords:
arenespolycyclic aromatic hydrocarbonspolyphenyl aromatic compoundsstrained molecules

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Area of Science:

  • Organic Chemistry
  • Supramolecular Chemistry
  • Crystallography

Background:

  • Polycyclic aromatic hydrocarbons (PAHs) with extensive phenyl substitutions exhibit unique structural and electronic properties.
  • Steric hindrance in highly substituted PAHs can lead to significant deviations from planarity.
  • Chirality and racemization dynamics are crucial aspects of molecular stability and function.

Purpose of the Study:

  • To synthesize and characterize novel poly-phenylated phenanthrenes, specifically 1,2,3,4,5,6,7,8-octaphenylphenanthrene and decaphenylphenanthrene.
  • To investigate the impact of extensive phenyl substitution on the molecular geometry and conformational flexibility of the phenanthrene core.
  • To determine the configurational stability and racemization barriers of these sterically hindered molecules.

Main Methods:

  • Short synthetic routes involving tetraphenylfuran and polybrominated benzene derivatives.
  • X-ray crystallography for detailed structural elucidation of the synthesized compounds.
  • Chiral chromatography for the resolution of enantiomers.
  • Determination of activation energy for racemization via experimental measurements and computational studies.

Main Results:

  • Successful synthesis of 1,2,3,4,5,6,7,8-octaphenylphenanthrene (4) and decaphenylphenanthrene (5) in two to three steps.
  • X-ray structures revealed significant twisting of the phenanthrene cores (approx. 40°) due to steric clashes between phenyl groups.
  • Compound 4 was resolved, with a determined free energy of activation for racemization of 24.6 kcal/mol at 40°C.
  • Computational studies predicted a racemization barrier for compound 5 that is ~6 kcal/mol lower than that of compound 4.

Conclusions:

  • Extensive phenyl substitution in phenanthrene derivatives leads to highly non-planar, sterically congested structures.
  • The degree of steric hindrance directly influences the racemization barrier and configurational stability.
  • Decaphenylphenanthrene is predicted to be configurationally unstable at room temperature, highlighting the limits of molecular stability under extreme steric pressure.