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 (T-4) are stabilized by multiple strong interactions with two anions. Hydrogen bonding/ion pairing of the anions are combined with anion-pi recognition to produce columnar architectures. In bilayer membranes, low transport activity is observed when the T-4 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-pi interactions can serve as artificial supramolecular channels for transporting anions across lipid bilayer membranes.