Selective Water Pore Recognition and Transport through Self-Assembled Alkyl-Ureido-Trianglamine Artificial Water Channels

[Image: see text] In nature, aquaporins (AQPs) are proteins known for fast water transport through the membrane of living cells. Artificial water channels (AWCs) synthetic counterparts with intrinsic water permeability have been developed with the hope of mimicking the performances and the natural functions of AQPs. Highly selective AWCs are needed, and the design of selectivity filters for water is of tremendous importance. Herein, we report the use of self-assembled trianglamine macrocycles acting as AWCs in lipid bilayer membranes that are able to transport water with steric restriction along biomimetic H-bonding-decorated pores conferring selective binding filters for water. Trianglamine [(±)Δ, (mixture of diastereoisomers) and (R,R)(3)Δ and (S,S)(3)Δ], trianglamine hydrochloride (Δ.HCl), and alkyl-ureido trianglamines (n = 4, 6, 8, and 12) [(±)ΔC4, (±)ΔC8, (±)ΔC6, and (±)ΔC12] were synthesized for the studies presented here. The single-crystal X-ray structures confirmed that trianglamines form a tubular superstructure in the solid state. The water translocation is controlled via successive selective H-bonding pores (a diameter of 3 Å) and highly permeable hydrophobic vestibules (a diameter of 5 Å). The self-assembled alkyl-ureido-trianglamines achieve a single-channel permeability of 10(8) water molecules/second/channel, which is within 1 order of magnitude lower than AQPs with good ability to sterically reject ions and preventing the proton transport. Trianglamines present potential for engineering membranes for water purification and separation technologies.