Synthesis, structure, and electrochemical properties of [2.2]paracyclophane[4,5-d]trithiole

摘要

A novel five-membered trithiole with sulfur-sulfur linkages bound to a [2.2]paracyclophane framework with low-redox potential has been synthesized. Characterization of the new trithiole was performed by X-ray crystallographic analysis. The cyclic voltammogram of the trithiole showed well-defined reversible electrochemical redox coupled with low-oxidation potential. Novel radical cation salt was isolated in quantitative yield in the one-electron oxidation of the trithiole with one equivalent of NOPF6 as a one-electron oxidant. The structure of the radical cation salt was analyzed by ~(31)P NMR and EPR spectroscopies and elemental analysis. The salt underwent one-electron reduction on treatment with one equivalent of samarium(II) iodide to give the neutral starting trithiole quantitatively.