Heavy Pnictogenium Cations as Transmembrane Anion Transporters in Vesicles and Erythrocytes.

Our work on the complexation of fluoride anions using group 15 Lewis acids has led us to investigate the use of these main group compounds as anion transporters. In this paper, we report on the anion transport properties of tetraarylstibonium and tetraarylbismuthonium cations of the general formula [Ph3PnAr]+ with Pn = Sb or Bi and with Ar = phenyl, naphthyl, anthryl, or pyrenyl. Using EYPC-based large unilamellar vesicles, we show that these main group cations transport hydroxide, fluoride and chloride anions across phospholipid bilayers. A comparison of the properties of [Ph3SbAnt]+ and [Ph3BiAnt]+ (Ant = 9-anthryl) illustrates the favorable role played by the Lewis acidity of the central pnictogen element with respect to the anion transport. Finally, we show that [Ph3SbAnt]+ accelerates the fluoride-induced hemolysis of human red blood cells, an effect that we assign to the transporter-facilitated influx of toxic fluoride anions.