Fixed or Invertible Calixarene-Based Directional Shuttles

The first examples of rotaxanes based on calixarenes threaded by dialkylammonium ions, which also represent the first examples of calixarene-based molecular shuttles, are reported. The base/acid treatment demonstrated that these systems act as molecular shuttles, which move between three sites on the axle. When small OMe groups are appended at the calix[6]arene lower rim an unprecedented inversion of its shuttling direction is observed, which occurs through a cone-to-cone inversion of the macrocycle.