Efficient self-sorting of a racemic tetra-urea calix[4]pyrrole into a single heterodimeric capsule

A racemic calix[4]pyrrole self-sorts into a single achiral heterodimeric capsule. This process is induced either by encapsulation of one ditopic or two monotopic N-oxide guests. The influence of the guest structure in the dynamics of the disproportionation process of the two homochiral capsules is reported. The unidirectional sense of rotation of the urea groups assigned to the heterodimeric capsule is explained as the outcome of an induction of chirality from the stereogenic centers.