Supramolecular chemistry of monochiral naphthalenediimides

Org Biomol Chem. 2011 Nov 7;9(21):7547-53. doi: 10.1039/c1ob06147j. Epub 2011 Sep 22.

Abstract

Three new N-desymmetrised naphthalenediimides (NDIs) are described, each containing one chiral and one achiral centre. The ability of such 'monochiral' NDIs to self-assemble into hydrogen-bonded helical nanotubes, to act as a sergeant in a 'sergeants-and-soldiers' system and to form a hexameric receptor for C(70) was examined. Small differences at the achiral centre were found to have significant effects on the supramolecular properties of the NDI. All three new NDIs form nanotubes that bind C(60), but with different efficiencies, and one is a better sergeant than any of the dichiral NDIs investigated to date.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Imides / chemical synthesis
  • Imides / chemistry*
  • Macromolecular Substances / chemical synthesis
  • Macromolecular Substances / chemistry
  • Molecular Structure
  • Naphthalenes / chemical synthesis
  • Naphthalenes / chemistry*
  • Stereoisomerism

Substances

  • Imides
  • Macromolecular Substances
  • Naphthalenes
  • naphthalenediimide