Cyclopentannulated Decacyclenes as Carbon-Based Multistage Electron Acceptors.

ABSTRACT: We report a series of cyclopentannulated decacyclenes that act as remarkable multistage electron acceptors. The compounds were synthesized in a modular approach via Yamamoto cyclotrimerization of brominated pyracylene precursors, allowing the introduction of electron-withdrawing, -donating, and solubilizing fluoro, methoxy, and tert-butyl moieties, respectively. The subsequent π-expansion of the polycyclic scaffold was achieved by oxidative cyclodehydrogenation. X-ray crystallographic analysis revealed the propeller-shaped geometry of the decacyclene core with a pronounced bond length alternation in the central six-membered ring and the columnar packing motif in the solid state. Depending on the substitution pattern, the compounds are capable of up to six reversible reductions within a par

SUBMITTER: Eiden SC 

PROVIDER: S-EPMC12447868 | biostudies-literature | 2025 Sep

REPOSITORIES: biostudies-literature