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

Sandwich 1(2).2, macrocyclic 1.3 and box 1(2).4(2) supramolecular assemblies were synthesized by the reaction of 1,8-bis(4-pyridylethynyl)anthracene 1 with hydroquinone 2, resorcinol 3 and 1,5-dihydroxynaphthalene 4 via 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.

Automated summary

The sandwich, macrocycle, and box supramolecular assemblies were synthesized from the reaction of 1,8-bis(4-pyridylethynyl)anthracene 1 with various phenolic compounds; investigation of their crystal structures indicated that the distance between two oxygen atoms in a hydrogen bonding donor is crucial for the formation of these supramolecular assemblies.