First Synthesis of the Inherently Chiral Trans ‐4′ Bisadduct of C 59 N Azafullerene by Using Cyclo‐ [2]‐dodecylmalonate as a Tether

The multiaddition chemistry of azafullerene C 59 N has been scarcely explored, and the isolation of pure bisadducts is in its infancy. Encouraged by the recent regioselective synthesis of the inherently chiral equatorial face bisadduct of C 59 N, we focused on the isolation of the first trans‐ 4 bisadduct in a simple two‐step approach. The first regioselective synthesis of the trans‐ 4 bisadduct of C 59 N by using cyclo‐ [2]‐dodecylmalonate as a tether is now reported. The newly synthesized bisadduct has C 1 symmetry, as evidenced by 13 C NMR, while X‐ray crystallography validated the trans‐ 4′ addition pattern. Furthermore, the inherently chiral trans‐ 4′ C 59 N bisadduct was enantiomerically resolved, and the mirror‐image relation of the two enantiomers was probed by circular dichroism spectroscopy. Finally, UV‐Vis and redox assays suggested that the addition pattern has a reflection in the light‐harvesting and redox properties of the bisadduct.