Constitutional Dynamic Chemistry pp 217-260

Part of the Topics in Current Chemistry book series (TOPCURRCHEM, volume 322)

Supramolecular Naphthalenediimide Nanotubes

  • Nandhini Ponnuswamy
  • Artur R. Stefankiewicz
  • Jeremy K. M. Sanders
  • G. Dan Pantoş
Chapter

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 C60, ion-pairs, and extended aromatic molecules. In the presence of C70 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.

Keywords

Circular dichroism Fullerenes Host–guest Ion-pairs Sergeants-and-soldiers Supramolecular chemistry Supramolecular polymers 

Copyright information

© Springer-Verlag Berlin Heidelberg 2011

Authors and Affiliations

  • Nandhini Ponnuswamy
    • 1
  • Artur R. Stefankiewicz
    • 1
  • Jeremy K. M. Sanders
    • 1
  • G. Dan Pantoş
    • 2
  1. 1.Department of ChemistryUniversity of CambridgeCambridgeUK
  2. 2.Department of ChemistryUniversity of BathBathUK

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