Selenacrown Macrocycle in Aqueous Medium: Synthesis, Redox-Responsive Self-Assembly, and Enhanced Disulfide Formation Reaction

Organic selenides are famous for their coordination and catalytic functions in the organic phase, albeit challenging for aqueous medium. Herein, the combination of a hydrophilic body of crown ether and substitution of one oxygen atom with a selenium one provides a new type of design route for organic selenide entities with charming functions in aqueous solution. The selenacrown ether C9Se presented here intrinsically shows an amphiphile-like property. Its nanosphere structure in water readily expands the catalysis of organic selenide to aqueous substrates in thiol/disulfide conversion.

Automated summary

Organic selenides are well-known for their coordination and catalytic functions in organic phase, but pose challenges in aqueous medium. This study introduces a new design route for organic selenide entities with appealing functions in aqueous solution by combining the hydrophilic body of crown ether with substitution of oxygen atom with selenium. The selenacrown ether C9Se exhibits amphiphile-like property and expands the catalytic activity of organic selenides to aqueous substrates in thiol/disulfide conversion through its nanosphere structure in water.