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Tridecacyclene: A Cyclic Tetramer of Acenaphthylene.
Journal article

Tridecacyclene: A Cyclic Tetramer of Acenaphthylene.

  • Sumy DP Department of Chemistry, University of Vermont, Burlington, Vermont, 05405, USA.
  • Dodge NJ Department of Chemistry, University of Vermont, Burlington, Vermont, 05405, USA.
  • Harrison CM Department of Chemistry, University of Vermont, Burlington, Vermont, 05405, USA.
  • Finke AD Swiss Light Source, Paul Scherrer Institute, 5232, Villigen PSI, Switzerland.
  • Whalley AC Department of Chemistry, University of Vermont, Burlington, Vermont, 05405, USA. Adam.Whalley@uvm.edu.
  • 2016-01-22
Published in:
  • Chemistry (Weinheim an der Bergstrasse, Germany). - 2016
Lewis acids
arenes
buckminsterfullerene
polycyclic aromatic hydrocarbons
supramolecular chemistry
Acenaphthenes
Catalysis
Cyclization
Lewis Acids
Molecular Structure
English In this manuscript, we describe the single-step preparation of a cyclic tetramer of acenaphthylene through a Lewis acid-catalyzed aldol cyclization of 1-acenaphthenone. The previously unexplored cyclic tetramer material differs from the better-known cyclic trimer, decacyclene, due to the presence of a central eight-membered ring. This ring not only forces the molecule to distort significantly from planarity, but is also responsible for its unique electronic properties, including a decrease in the reduction potential (by about 0.4 eV) and optical gap (by about 0.73 eV), compared to the more planar decacyclene. The synthesized compound crystallizes into a unique packing structure with significant π-stacking observed between adjacent molecules. Furthermore, due to its saddle-like shape, the cyclic tetramer is able to form shape-complementary interactions between its concave surface and the convex outer surface of buckminsterfullerene to generate cocrystalline supramolecular assemblies.
Language
  • English
Open access status
closed
Identifiers
Persistent URL
https://sonar.ch/global/documents/159479
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