Structural changes in the guest cause inversion of the dominant threading direction in triptycene derived oxacalixarene with different semi-cavities.

A new kind of triptycene-derived calix [6]arene analogue was synthesized by two different routes. The triptycene-derived calix[6]arene analogues show highly symmetric structures and fixed conformations in solution, and can self-assemble into organic tubular structures with aromatic rings as the wall in the solid state. Moreover, the calix[6]arene analogue with two 1,8-dihydroxyltriptycene moieties in the cis position was also found to form stable complexes with paraquat derivatives with different terminal functional groups. Consequently, a [2]rotaxane assembly based on the calix[6]arene analogue was further constructed. † Electronic supplementary information (ESI) available: Synthesis and characterization data of new compounds. Variable-temperature 1 H NMR experiments. X-ray crystal data and crystal packing. Determination of the association constants. ESI-MS spectra of the complexes. CCDC 931895-931898, 931783. For ESI and crystallographic data in CIF or other electronic format see