Formation of sandwich, macrocyclic and box supramolecular assemblies that were controlled by the distance of two oxygen atoms in hydrogen bonding donors

Sandwich 1₂·2, macrocyclic 1·3 and box 1₂·4₂ supramolecular assemblies were synthesized by the reaction of 1,8-bis(4-pyridylethynyl)anthracene 1 with hydroquinone 2, resorcinol 3 and 1,5-dihydroxynaphthalene 4via hydrogen-bonding interactions, respectively. The formed sandwiches, macrocycles and boxes can further self assemble to form a double-layer supramolecular polymer, nanotubes and a one-dimensional “iron chain type” supramolecular polymer. Investigation of their crystal structures revealed that the distance between two oxygen atoms in a hydrogen bonding donor play an important role in the formation of supramolecular assemblies.