Kinetically controlled self-assembly of pseudorotaxanes on crystallization

Mixing of equimolar amounts of cyclobis(paraquat-p-phenylene) (CBPQT(4+)) with a bis-4-methylphenyl ether (MPE twice) of a 1,5-dioxynaphthalene (DNP) derivative in MeCN/CH2Cl2 (3:1) results in the formation of a [2]pseudorotaxane which, on crystallization, yields a [4]pseudorotaxane in the solid state that is stabilized by multiple [C-(HF)-F-...] interactions: a mixture of the same components in a 1:3 ratio affords a crystalline [2]pseudorotaxane after vapor diffusion of methyl-tert-butyl ether into a solution of these components in MeCN/CH2Cl2 (3:1).