Self-Assembling Cyclophanes and Catenanes Possessing Elements of Planar Chirality

Spontaneous resolution upon crystallization A cyclophane and two [2]catenanes possessing elements of planar chirality have been self-assembled in good yields. In particular, the [2]catenane (right) incorporating cyclobis(paraquat-1,5-naphthalene) and bis-1/5-dioxynaphtho[38]crown-10, possesses four elements of planar chirality and can exist as a mixture of six diastereoisomeric pairs of enantiomers, a total of twelve stereoisomers. However, spontaneous resolution occurs upon crystallization and only one out of the twelve possible stereoisomers is observed in the solid state.