A highly active and selective chalcogen bond-mediated perchlorate channel

Abstract

Artificial membrane transporters that either use chalcogen bonds to facilitate transmembrane flux of anions or show high selectivity toward perchlorate anions are rare. In this work, we report on one such novel monopeptide-based transporter system, featuring both chalcogen bonds for highly efficient anion transport and high transport selectivity toward ClO4− anions. Structurally, these monopeptide molecules associate with each other via H-bonds to produce H-bonded 1D stack that not only one dimensionally but also directionally aligns the terminal bicyclic thiophene motifs to the same side. Functionally, these well-aligned thiophenes create a sulfur-rich transmembrane pathway, combinatorially fine-tunable to enable anions to efficiently cross the membrane in the increasing activity of Cl− < Br− < NO3− < ClO4−via chalcogen bonds, with EC50 values of 0.75, 0.40, 0.37 and 0.093 µmol/L (0.3 mol% relative to lipid molecules), respectively.