Reversibly Redox‐Switchable Anionic Surfactant Contains Two Selenium Atoms

Abstract

To better control the interfacial activities of selenium‐containing surfactants, a redox‐switchable anionic surfactant containing 2 selenium atoms, namely sodium 3‐((3‐(benzylselanyl)propyl)selanyl)propyl sulfate (SBSe2S), has been designed and synthesized. Upon oxidation by H2O2, the 2 divalent selenide groups in the hydrophobic tail of SBSe2S are converted into the corresponding selenoxides. The initial hydrophobic tail of SBSe2S gets separated into 3 segments by 2 hydrophilic selenoxide groups, destroying the bola‐type structure. The interfacial activities of SBSe2S in aqueous solution could thereby be switched off to a greater degree than in the case of its counterparts containing only a single selenium atom. After reduction with Na2SO3, the 2 selenoxide groups in SBSe2S‐Ox are restored to the initial selenide. Consequently, the interfacial activities of SBSe2S could be reversibly switched by alternate addition of H2O2 and Na2SO3, without obvious deterioration over 5 cycles.