Heteroanalogues of PCBM: N-bridged imino-PCBMs for organic field-effect transistors.

Crossing the bridge: Two isomeric iminofullerenes, [5,6]-open azafulleroid 1 and [6,6]-closed aziridinofullerene 2, were prepared by cycloaddition of an organic azide to C(60). These "azalogues" enable the study of the effects of the bridging atom in a fullerene cage, that is, C(60)-like (5,6-open) versus PCBM-like (6,6-closed), as a function of their pi systems (PCBM = [6,6]-phenyl-C(61)-butyric acid methyl ester).