[GRAPHICS]
The template directed syntheses of two [2]rotaxanes, one carrying one and t
he other two triphenylphosphonium stoppers, have been achieved using a thre
ading-followed-by-stoppering approach. Either one or two benzylic bromide f
unctions-located at the para positions of dibenzylammonium-based ions, whic
h become encircled by dibenzo[24]crown-8 macrocycles during the initial the
rmodynamically controlled phases that mark the recognition events-serve as
sites for nucleophilic attack by triphenylphosphine during the subsequent k
inetic stages that lead to the formation of the two [2]rotaxanes.