A new approach to porphyrinofullerene donor-acceptor dyads, based on consecutive 1,3-dipolar cycloaddition of azomethine ylides, generated from bis-aziridinedicarboxylate, to C60 and to porphyrin with a maleimidophenyl substituent, was developed. A synthesis of the axially symmetric porphyrin-fullerene-C60 ensemble 5 with a novel rigid pyrrolo[3,4-c]pyrrolic linker was realized. Theoretical, electrochemical, and spectroscopic studies of compound 5 showed that it is capable of forming a charge-separated state. © 2013 American Chemical Society.
Konev, A. S., Khlebnikov, A. F., Nikiforova, T. G., Virtsev, A. A., & Frauendorf, H. (2013). Synthesis, spectroscopic and electrochemical properties of axially symmetric fullerene-porphyrin dyad with a rigid pyrrolo[3,4-c]pyrrole spacer. Journal of Organic Chemistry, 78(6), 2542-2552. https://doi.org/10.1021/jo302763a