Piling up pillar[5]arenes to self-assemble nanotubes

New liquid-crystalline pillar[5]arene derivatives have been prepared by grafting first-generation Percec-type poly(benzylether) dendrons onto the macrocyclic scaffold. The molecules adopt a disc-shaped structure perfectly suited for self-organization into a columnar liquid-crystalline phase. In this way, the pillar[5]arene cores are piled up, thus forming a nanotubular wire encased within a shell of peripheral dendrons. The capability of pillar[5]arenes to form inclusion complexes has been also exploited. Specifically, detailed binding studies have been carried out in solution with 1,6-dicyanohexane as the guest. Inclusion complexes have also been prepared in the solid state. Supramolecular organization into the Col mesophase has been deduced from X-ray diffraction data and found to be similar to that observed within the crystal lattice of a model inclusion complex prepared from 1,4-dimethoxypillar[5]arene and 1,6-dicyanohexane.Financial support by the International Center for Frontier Research in Chemistry, the LabEx “Chimie des SystÀmes Complexes”, the Spanish Ministerio de Economía y Competitividad (MINECO; project CTQ2015-70174-P), the Swiss National Science Foundation (grant number: 200020-152716), and the Tunisian Ministry of Higher Education and Scientific Research and Technology is gratefully acknowledged.Peer Reviewe