Threading of three rings on two stations: a convergent approach to [4]rotaxane.

A novel approach to efficient and selective construction of [4]rotaxane was proposed to demonstrate the superiority of H-bonded azo-macrocycles in forging higher order rotaxanes. The single crystal structure reveals the importance of the interplay of multiple non-covalent bonding interactions, particularly π-stacking interactions, in stabilizing the host-guest complex. This may open an avenue to the synthesis of oligomeric mechanically interlocked molecules containing fewer stations but more rings.