Self‐Assembly of Size‐Controlled m‐Pyridine–Urea Oligomers and Their Biomimetic Chloride Ion Channels

Abstract

The m‐pyridine urea (mPU) oligomer was constructed by using the intramolecular hydrogen bond formed by the pyridine nitrogen atom and the NH of urea and the intermolecular hydrogen bond of the terminal carbonyl group and the NH of urea. Due to the synergistic effect of hydrogen bonds, mPU oligomer folds and exhibits strong self‐assembly behaviour. Affected by folding, mPU oligomer generates a twisted plane, and one of its important features is that the carbonyl group of the urea group orientates outwards from the twisted plane, while the NHs tend to direct inward. This feature is beneficial to NH attraction for electron‐rich species. Among them, the trimer self‐assembles into helical nanotubes, and can efficiently transport chloride ions. This study provides a novel and efficient strategy for constructing self‐assembled biomimetic materials for electron‐rich species transmission.

A Synthetic Phospholipid Derivative Mediates Ion Transport Across Lipid Bilayers

“…As illustrated in Figure 3F , the addition of FCCP caused obviously increased activity (from 50 to 80% by adding 5.0 μM FCCP), in contrast, the same amount of FCCP itself resulted <10% activity. This result support that M + /OH − symport mechanism balanced the charges inside and outside of the LUVs (Saha et al, 2016 ; Chen et al, 2018b , 2021 ).…”

Supramolecular chemistry in lipid bilayer membranes

“…These compounds were found to reliably stack inside the lipid bilayer via hydrogen bonding, forming a chloride-selective channel (0.5 mol % transporter relative to lipid). 110 Very recently, Zeng and coworkers have also optimised their water transport foldamer systems further to achieve remarkable H 2 O transport rates outperforming aquaporins, and with proton exclusion, by using a membrane-spanning foldamer with a hydrophobic pore. 111…”

“Urea to Urea” Approach: Access to Unsymmetrical Ureas Bearing Pyridyl Substituents

“…In addition to the medicinal application, N-pyridylureas are demanded in material science. Particularly, many recent studies focus on the utilization of 2-pyridylurea-based compounds as ion sensors, [28][29][30][31][32] ligands of organometallic catalysts for polysiloxanes production, [33,34] self-assembled biomimetic materials for electron-rich species transmission, [35] agents for polymer functionalization through multiple hydrogen bonding, [36] and antibacterial supramolecular gels. [37] Furthermore, the successful utility of pyridylurea derivatives in the synthesis of foldamers with improved chiroptical properties has been shown.…”