Engineering Discrete Stacks of Aromatic Molecules

Chem Soc Rev. 2009 Jun;38(6):1714-25. doi: 10.1039/b901261n. Epub 2009 May 6.


Intrigued by transannular interactions occurring in stacked aromatic molecules, chemists have long endeavored to engineer discrete stacks of specific lengths and orientation. The maturation of self-assembly methodologies has shifted the focus away from utilizing covalent scaffolds to harnessing non-covalent interactions such as ionic interactions, hydrogen bonds, metal-ligand interactions, and aromatic interactions. Aromatic molecules often assemble into ill-defined, infinite aggregates and thus multiple self-assembly techniques must be combined to achieve the desired stack size and conformations. This critical review briefly highlights covalent scaffolds of stack aromatics before focusing on modern self-assembly based strategies for engineering discrete stacks of aromatic molecules (149 references).

Publication types

  • Review

MeSH terms

  • Anthracenes / chemistry
  • Hydrogen Bonding
  • Metals / chemistry
  • Molecular Conformation*
  • Organic Chemicals / chemistry*
  • Static Electricity


  • Anthracenes
  • Metals
  • Organic Chemicals
  • catenane