Synthesis and Characterization of the First Corannulene Cyclophane

T. Jon Seiders, Kim K. Baldridge, and Jay S. Siegel

Contribution from
  • The University of California, San Diego, and
  • San Diego Supercomputer Center
  • Synopsis

    Fullerene fragments, such as corannulene, inspire the design of several cyclophane motifs, such as ansa-baskets, covered-baskets, and tectonic-globes. Each of these related strutural types otentially serve as fullerene mimics with novel physical properties; for example, as fullernoid receptors, they would be precursors to endohedral complexes. Despite the abundance of novel molecular designs, the synthetic routes into these structures are not yet well developed. In particular, the synthetic challenge, although addressed in some elegant flash vacuum pyrolysis techniques, does not have a general solution for the prepartaion of keystones suitable as cyclophane precursors. In response to this synthetic challenge, we present the first synthesis of a corannulene based cyclophane (above), which showcases a new route into the corannulene nucleus.