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Keywords:

  • anthracene;
  • cyclophanes;
  • dimerization;
  • oxidation;
  • through-space interactions
Thumbnail image of graphical abstract

A strained relationship: Oxidation of dihydroxy-substituted acenes provides face-to-face [2.2]metacyclophane-like dimers (see scheme; O red, Si of iPr3Si groups blue). The products exhibited highly distorted structures caused by steric repulsion. UV/Vis and electrochemical analysis revealed that the HOMO–LUMO gap was decreased upon dimerization.