Supramolecular chemistry of monochiral naphthalenediimides

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 C₇₀ 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 C₆₀, but with different efficiencies, and one is a better sergeant than any of the dichiral NDIs investigated to date.