Tether-DirectedElectrosynthesisof Bicyclic [60]FullereneDerivatives Fused with 5‑Membered Azacycle and 13-MemberedCarbocycle

Tether-directed electrosynthesis of [60]fullerene derivatives fused with 5-membered azacycle and 13-membered carbocycle, that is, bicyclic 1,4,9,12- and 1,2,4,15-adducts, has been achieved unexpectedly for the first time. The novel bicyclic [60]fullerene derivatives are obtained by the electrochemical reduction of [60]fullerene-fused indolines or lactams and subsequent regioselective cyclization with 2,2″-bis(bromomethyl)-1,1′:3′,1″-terphenyl. The product structures have been characterized by spectroscopic data and single-crystal X-ray analysis.