Self‐Assembled Columnar Triazole Quartets: An Example of Synergistic Hydrogen‐Bonding/Anion–π Interactions

The self‐assembly of triazole amphiphiles was examined in solution, the solid state, and in bilayer membranes. Single‐crystal X‐ray diffraction experiments show that stacked protonated triazole quartets (T₄) are stabilized by multiple strong interactions with two anions. Hydrogen bonding/ion pairing of the anions are combined with anion–π recognition to produce columnar architectures. In bilayer membranes, low transport activity is observed when the T₄ channels are operated as H⁺/X^? translocators, but higher transport activity is observed for X^? in the presence of the K⁺‐carrier valinomycin. These self‐assembled superstructures, presenting intriguing structural behaviors such as directionality, and strong anion encapsulation by hydrogen bonding supported by vicinal anion–π interactions can serve as artificial supramolecular channels for transporting anions across lipid bilayer membranes.