A New Functional Bis(m-phenylene)-32-crown-10-Based Cryptand Host for Paraquats

The pseudorotaxane complex of the new hydroxymethyl cryptand 3 with N,N'-dimethyl-4,4'-bipyridinium bis(hexafluorophosphate), PQ(PF6)(2), has an association constant of 2.0(+/- 0.3) x 10(4) M-1. In the crystal structure of 3 center dot PQ(PF6)(2) one of the bonding elements appears to be an aromatic edge-to-face interaction of a paraquat beta-proton with the hydroquinone moiety; this is the first time this interaction has been reported between a cryptand and paraquat.