Unveiling the regioselectivity of rhodium(I)-catalyzed [2 + 2 + 2] cycloaddition reactions for open-cage C70 production

Abstract

The regioselective functionalization of fullerenes holds significant promise for applications in the field of medicinal chemistry, material science and photovoltaics. In this study, we investigate the regioselectivity of the rhodium(I)-catalyzed [2+2+2] cycloaddition reaction between diynes and C70 as a novel procedure for generating C70 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 synthesised bis(fulleroids) afford open-cage C70 derivatives having a 12-membered ring opening

We are grateful for the financial support from the Ministerio de Ciencia e Innovación and EU (Project PID2020-113711GB-I00 MCIN/AEI/10.13039/50110001103, FPI predoctoral grant to C.C. and Margarita Salas grant (NextGenerationEU) to A.A.) and the Generalitat de Catalunya (Project 2021-SGR-623)