Fig. 1. PDI (1, 2) or NDI (3), containing components that are used to synthesise handcuff rotaxanes. Note the simple design of each component, either a bis-pillar[5]arene or bis-imidazole appended to an aromatic core. Handcuff formation is readily achieved through the formation of pseudo-rotaxanes between imidazole and pillar[5]arene moieties followed by stoppering through reaction of the imidazole groups and benzyl iodides. Model bis-imidazolium rods, 6 and 7, are studied for comparison.