Preparation of a Reversible Redox-Controlled Cage-Type Molecule Linked by Disulfide Bonds



A unique trithiol macromolecule, with an intrinsic conformational propensity for dimerization (cage) instead of oligomerization upon oxidation, was prepared straightforwardly through rational design. The quantitative conversion and the reversibility between the cage and trithiols through redox reactions were assayed by 1H NMR spectroscopic analysis. The X-ray structure of the synthesized cage-type molecule represents the first successful example of a redox-controlled reversible dimeric capsule linked through covalent disulfide bonds. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)