Ion transport through bilayer membranes mediated by pyrogallol[4]arenes

•Many relatively short-chained pyrogallolarenes function as amphiphiles.•New branched chain pyrogallolarenes are membrane active.•3-Pentylpyrogallolarene forms a unique nanotube that forms conducting pores.•Isopropylpyrogallolarene forms stable monolayers and ion-conducting pores.

Pyrogallol[4]arenes result from the condensation of 1,2,3-trihydroxybenzene and an aldehyde. The compounds studied have linear and branched sidechains: n-propyl, isopropyl, 3-pentyl, n-hexyl, 4-heptyl, n-octyl, n-undecyl, and n-dodecyl. The ability of these compounds to form pores in bilayer membranes, their aggregation behavior, and their ion transport behavior have been studied. The n-alkyl and branched alkyl chained derivatives show significantly different behavior in their membrane activity.

Graphical abstractStraight and branched chain pyrogallolarenes are amphiphiles and mediate the transport of metallic cations and chloride anions through phospholipid bilayer membranes.Figure optionsDownload full-size imageDownload as PowerPoint slide