Fullerene-Centered Dissymmetric Molecular Triads

Significance

In this report, Saigo et al. prepared [60]fullerene-centered dissymmetric molecular triads by successive titanium-catalyzed imine formation reactions. Bis(formylmethano)[60]fullerene was synthesized from [60]fullerene and a bis(sulfonium ylide) with the ‘out/out-equatorial’ bisadduct as a major regioisomer. One of the two formyl groups is much more reactive than the other toward imine formation, which the authors attribute to the different steric environment imposed by the ‘tether’. Various aryl amines, including electron-rich or -deficient, perylenyl, and porphyrinyl, were used to provide the products in satisfactory yields.