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The regioselective functionalization of fullerenes holds significant promise for applications in the fields of medicinal chemistry, materials science, and photovoltaics. In this study, we investigate the regioselectivity of the rhodium(I)-catalyzed 2 + 2 + 2 cycloaddition reactions between diynes and C 70 as a novel procedure for generating C 70 bis(fulleroid) derivatives. The aim is to shed light on the regioselectivity of the process through both experimental and computational approaches. In addition, the photooxidation of one of the C–C double bonds in the synthesized bis(fulleroids) affords open-cage C 70 derivatives having a 12-membered ring opening.
Castanyer et al. (2024) studied this question.