Supramolecular naphthalenediimide nanotubes

Top Curr Chem. 2012:322:217-60. doi: 10.1007/128_2011_305.

Abstract

Amino acid functionalized naphthalenediimides (NDIs) when dissolved in chloroform form a dynamic combinatorial library (DCL) in which the NDI building blocks are connected through reversible hydrogen bonds forming a versatile new supramolecular assembly in solution with intriguing host-guest properties. In chlorinated solvents the NDIs form supramolecular nanotubes which complex C(60), ion-pairs, and extended aromatic molecules. In the presence of C(70) a new hexameric receptor is formed at the expense of the nanotube; the equilibrium nanotube - hexameric receptor can be influenced by acid-base reactions. Achiral NDIs are incorporated in nanotubes formed by either dichiral or monochiral NDIs experiencing the "sergeants-and-soldiers" effect.

Publication types

  • Review

MeSH terms

  • Circular Dichroism
  • Combinatorial Chemistry Techniques / methods*
  • Imides / chemical synthesis*
  • Imides / chemistry
  • Nanotubes / chemistry*
  • Naphthalenes / chemical synthesis*
  • Naphthalenes / chemistry
  • Polycyclic Aromatic Hydrocarbons / chemistry

Substances

  • Imides
  • Naphthalenes
  • Polycyclic Aromatic Hydrocarbons
  • naphthalenediimide