Constitutional Dynamic Chemistry pp 217-260
Supramolecular Naphthalenediimide Nanotubes
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.