[1]Rotaxanes based on monosubstituted phosphorus-containing pillar[5]arenes have been synthesized for the first time by the Kabachnik–Fields reaction in good yields. The introduction of the bulky phosphoryl functionalized stopper led to the formation of the [1]rotaxane core. It was found that the [1]rotaxanes were robust and unaffected by changes in the temperature or solvent.