Anion Recognition through Multivalent C–H Hydrogen Bonds: Anion-Induced Foldamer Formation and Transport across Phospholipid Membranes

Abstract

A series of triazole–cyanostilbene receptors were designed and synthesized. The receptor binds with the anions through various CH···anion hydrogen bonding interactions, where strong binding was observed for SO42– anions followed by Cl–, Br–, NO3–, and I–, calculated from the 1H NMR titration experiment. The NOESY NMR experiment of the receptor confirmed the formation of anion-induced folded conformation. The CH···anion hydrogen bonding interaction-mediated anion recognition and foldamer formation were further confirmed from geometry optimization studies of the anion-bound complex. The receptor transports Cl– anions efficiently compared to SO42– anions across the lipid bilayer membrane via a mobile carrier mechanism.