1.D.294. The Self-Assembled Alkyl-Ureido-Trianglamine Artificial Water Channel (AWC2) Family

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)₃Δ and (S,S)₃Δ], trianglamine hydrochloride (Δ.HCl), and alkyl-ureido trianglamines (n = 4, 6, 8, and 12) [(±)ΔC4, (±)ΔC8, (±)ΔC6, and (±)ΔC12] have been synthesized (Andrei et al. 2023). The single-crystal X-ray structures confirmed that trianglamines form tubular superstructures in the solid state. 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 10⁸ water molecules/second/channel, which is ~1 order of magnitude lower than AQPs with good ability to sterically reject ions and preventing proton transport. Trianglamines present potential for engineering membranes for water purification and separation technologies.

References:

Andrei, I.M., A. Chaix, B.T. Benkhaled, R. Dupuis, C. Gomri, E. Petit, M. Polentarutti, A. van der Lee, M. Semsarilar, and M. Barboiu. (2023). Selective Water Pore Recognition and Transport through Self-Assembled Alkyl-Ureido-Trianglamine Artificial Water Channels. J. Am. Chem. Soc. 145: 21213-21221.