Iodide-Selective Synthetic Ion Channels Based on Shape-Persistent Organic Cages

We report here a synthetic ion channel
developed from a shape-persistent
porphyrin-based covalent organic cage. The cage was synthesized by
employing a synthetically economical dynamic covalent chemistry (DCC)
approach. The organic cage selectively transports biologically relevant
iodide ions over other inorganic anions by a dehydration-driven, channel
mechanism as evidenced by vesicle-based fluorescence assays and planar
lipid bilayer-based single channel recordings. Furthermore, the organic
cage appears to facilitate iodide transport across the membrane of
a living cell, suggesting that the cage could be useful as a biological
tool that may replace defective iodide channels in living systems.