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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 associated with 1.D.294 family:

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. 37750755