Baskets, covered baskets, and basket balls: corannulene based cyclophanes as fullerene mimics

Three cyclophanes based on corannulene have been synthesized. Aryl and alkyl groups have been strapped across the corannulene nucleus and a dimeric corannulene cyclophane has been prepared. The structure and conformational analysis of these compounds have been elucidated by NMR and ab initio quantum mechanical methods. The specific NMR effect of the corannulene system on the adjacent nuclei is discussed. These cyclophanes exhibit novel structures and are prototypical fullerene mimics.