Supramolecular approaches for chloride transport

Abstract

This thesis reports three different species of novel anion receptors designed to address current challenges in the field of transmembrane anion transport. The chloride (Cl−) binding affinities of the receptors were assessed, and their transport activities were investigated in model synthetic vesicle systems. In Chapter 2, carbazole was used as the scaffold for a series of 1,8-bis-(thio)urea compounds appended with a variety of electron-withdrawing groups. The compounds exhibited a structural change in the presence of excess Cl−, and high levels of anion transport activity were exhibited by the most efficient compounds in the series, with a preference for non-selective anion transport. Chapter 3 explored the transport activity of a series of isoquinoline-appended Pt(II) complexes in synthetic model vesicles for the first time. Anionophoric activity was observed to be heavily dependent on lipophilicity, with a preference for non-selective anion transport. The most active complexes were also tested in vitro, and apoptosis was induced in cancerous cell lines, which highlighted the therapeutic potential for these complexes. In Chapter 4, a series of calix[4]pyrroles were appended with squaramides, and their anion transport activities were investigated for the first time. The compounds exhibited improved transport properties compared to the unsubstituted meso-octamethylcalix[4]pyrrole, with a preference for non-selective anion transport. The results highlighted the significant impact of a single substituent on the transport activity of the calix[4]pyrrole scaffold.