Synthetic anion transporters show much promise as potential anti-cancer agents and therapeutics for diseases associated with mis-regulated protein anion channels, such as Cystic Fibrosis. There is a pressing need to develop synthetic carriers that facilitate highly selective ion transport whilst maintaining their high activity, particularly to avoid competing proton or hydroxide transport which dissipates cellular pH gradients. The utilisation of sigma-hole interactions such as halogen bonding (XB) and chalcogen bonding (ChB) in synthetic anion transporters is underdeveloped, yet their high directionality and hydrophobicity make them encouraging alternatives to acidic hydrogen bond donors. We have previoulsy shown that acyclic iodotriazole XB donors show enhanced chloride over hydroxide selectivity, binding strength and transport activity over hydrogen bonding analogues. Here, highly active bidentate XB and ChB anion carriers based on electron deficient iodo- and telluromethyl- triazole derivatives are reported, entitled 1.XB and 1.ChB respectively. Anion transport experiments reveal record nanomolar chloride transport activity for the bidentate halogen bonding anion carrier, and remarkably high chloride over proton/hydroxide selectivity for the chalcogen bonding anionophore.

Highly active halogen bonding and chalcogen bonding chloride transporters with non-protonophoric activity

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ACS Fall 2022

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.