Edge-Extended Kekulenes

  • Author: ChemistryViews
  • Published: 22 August 2021
  • Copyright: Wiley-VCH GmbH
  • Associated Societies: American Chemical Society (ACS), USA
thumbnail image: Edge-Extended Kekulenes

Kekulene is a cycloarene, i.e., a macrocycle composed of benzene units. Kekulene has a hexagonal structure with three benzene units at each edge. Extending these edges with further benzene rings would lead to [m,n]cycloarenes, with m and n equal to the numbers of benzene units on two adjacent edges. In this notation, kekulene derivatives are denoted as [3,3]cycloarenes.


Jishan Wu, National University of Singapore and Joint School of National University of Singapore and Tianjin University, Fuzhou, China, and colleagues have synthesized [m,n]cycloarene derivatives with extended edges, i.e., [3,4]-, [3,5]-, [4,4]-, and [4,5]cycloarenes (latter pictured above). The team first prepared suitable macrocyclic precursors functionalized with vinyl ethers using Suzuki coupling reactions. Then, they used a bismuth(III) triflate-catalyzed cyclization reaction to close the remaining six-membered rings and obtain the desired cycloarenes.


The products were characterized using X-ray crystallography and NMR spectroscopy, as well as density functional theory (DFT) calculations. The team found that the π-electrons in the compounds' macrocyclic cores are mainly delocalized within individual benzene, naphthalene, or anthracene units at the edges (pictured in blue in the example above).


 

 

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