Two [2]rotaxanes are assembled in water from modular subunits relying on Cu(I)-catalyzed azide-alkyne "click" chemistry. For this purpose, 2,6-substituted naphthalene axles with solubilizing oligoethylene glycol (OEG) chains (n = 1 - 5), and propargyl termination are synthesized and examined for their propensity to form inclusion complexes with a dicationic Diederich-type cyclophane host. The dependence of pseudo-rotaxane formation on the linking chemistry between naphthalene core and OEG chain, and in the case of ester linkers on different spacer lengths is analyzed by titration experiments. In addition the inclusion complexes of two [2]rotaxanes were trapped using a water-soluble azide-functionalized stopper. Repetitive chromatography finally enabled the isolation of both mechanically interlocked [2]rotaxanes.
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