Templated synthesis of desymmetrized [2]catenanes with excellent translational selectivity

Desymmetrized [2]catenanes were synthesized and shown to exhibit excellent translational selectivity. The templated synthesis takes effect from the formation of pseudorotaxanes between pi-rich crown ethers and a pi-deficient pyromellitic (PmI) unit, followed by macrocyclization around the crown ethers with the creation of a bipyridinium (BPy) unit. The crown ethers preferably encircle the BPy unit in the resulting [2]catenanes in both solution and the solid state, as indicated by various spectroscopic analyses.