Macrocyclization and Molecular Interlocking via Mitsunobu Alkylation:  Highlighting the Role of C−H···O Interactions in Templating

A series of diimide-based macrocycles have been prepared using Mitsunobu-mediated alkylation as the macrocyclization step. These macrocycles could not be incorporated into [2]catenanes using previously established building blocks and coupling methodology. However, when one of the macrocycle syntheses was conducted in the presence of a dinaphtho crown ether, catenane formation was achieved. This result is discussed in terms of the ability of the components to establish intermolecular C−H···O hydrogen-bonding contacts.