Development of Biomimicking Artificial Water Channels based on Triazole-Amine and Gallic Acid Motifs

Abstract

Artificial water channels (AWCs) have attracted significant attention as synthetic analogues of biological water channels, with potential applications in desalination, water purification, and membrane-based separations. Inspired by natural water transport systems, such as Aquaporins, considerable efforts have been devoted to designing small molecules that facilitate selective and efficient water transport across lipid membranes. In this work, two different molecular frameworks were developed and analysed as potential candidates for artificial water channel systems: imine-bonded triazole amine-based molecules and gallic acid-based molecular scaffolds. In the first chapter of this thesis, triazole amine derivatives were investigated as AWC candidates. The 1,2,4-triazole unit with multiple nitrogen atoms, along with an exocyclic free amino group, provides a favourable hydrogen-bonding environment that can interact with water molecules and organise them into self-assembled networks. Such features are desirable for facilitating water transport while maintaining selectivity. Structural modifications were employed to obtain triazole amine-based molecules with suitable lipophilic properties to promote their incorporation into lipid bilayers. In the second chapter, gallic acid-derived molecular frameworks were explored as alternative scaffolds for AWC design. Gallic acid contains a 3,4,5-trihydroxybenzene core capable of extensive hydrogen bonding through multiple hydroxyl groups. To enhance membrane insertion, a library of compounds was designed with aliphatic alkoxy chains, while retaining hydrogen-bonding functionalities that may assist in water transport. These studies demonstrate two complementary molecular design strategies for developing AWC candidates. The results highlight the balance of hydrophobic membrane affinity as well as hydrogen-bonding propensity in designing efficient supramolecular systems that can serve as artificial water channel molecules. This work contributes to ongoing efforts in developing small molecule based systems that mimic Aquaporins, along with enhanced salt-rejection that may provide useful insights for the design of next-generation membrane-active materials.