Head-to-Tail and Back-to-Back Dimerization of an Open-Cage Fullerene Derivative through π–π Interaction-Based Self-Assembly

Abstract

Open-cage fullerene derivative <b>2</b>, C₅₉(O)₄(NAr)₂ (Ar = <i>p</i>-<i>t</i>BuC₆H₄), was prepared from <b>1</b>, C₆₀(O)₄(OH)₂(NAr)₂, through processes involving decarbonylation and elimination of the two hydroxyl groups. The phenyl groups in compound <b>2</b> act as chelating ligands for the fullerene cage and induce partial dimerization of <b>2</b> in solution. The single crystal X-ray structure of <b>2</b> shows strong intradimer π–π interactions and also weaker interdimer CH−π and π–π interactions