Three Protocols for the Formation of a [3]Pseudorotaxane <i>via</i> Orthogonal Cryptand-Based Host–Guest Recognition and Coordination-Driven Self-Assembly

A novel bis(m-phenylene)-32-crown-10-based cryptand 1 with a pyridine nitrogen atom outside on the third arm was designed and synthesized. Subsequently, host–guest complexation between cryptand 1 and a selection of bipyridinium guests has been studied. More interestingly, the [3]pseudorotaxane 2⊃52 was obtained in three methods by utilizing the noninterfering orthogonal nature of coordination-driven self-assembly and host–guest interactions.