The self-assembly of triazole-amphiphiles has been examined in homogenous solution, in the solid state and in the bilayer membranes. Single-crystal X-ray diffraction structures show that stacked protonated Triazole-quartets-T4 quartets are mutually stabilized by strong recognition with two inner anions. Anion Hbonding/ion-pairing are combined with anion-π recognition to produce columnar architectures, resulted through anion-π interactions between anions and triazole moieties of vicinal T 4 quartets. In bilayer membranes, low transport activity is observed when the T 4 channels are operated as H + /Xtranslocators, but higher transport activity is observed when Xtranslocation was performed in the presence of K +carrier valinomycin. The anions channel results are interpreted as arising from discrete stacks of T-quartets where transport of would occur through the stacked T 4 macrocycles. These self-assembled channels presenting amazing structural behaviours, directionality, strong anion encapsulation via H-bonding supported with vicinal anion-π interactions are proposed as artificial supramolecular channels that transport anions across lipid bilayer membranes.