Constitutional Dynamic Chemistry

Volume 322 of the series Topics in Current Chemistry pp 217-260


Supramolecular Naphthalenediimide Nanotubes

  • Nandhini PonnuswamyAffiliated withDepartment of Chemistry, University of Cambridge
  • , Artur R. StefankiewiczAffiliated withDepartment of Chemistry, University of Cambridge
  • , Jeremy K. M. SandersAffiliated withDepartment of Chemistry, University of Cambridge
  • , G. Dan PantoşAffiliated withDepartment of Chemistry, University of Bath Email author 

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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.


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