Two-fold enhancement of equatorial bis-PCBM-C₆₀ adducts using a supramolecular mask

ABSTRACT

Regioselective poly-functionalization of fullerenes is highly desired to boost the applicability of pure-isomer poly-adducts. Here, we show how the supramolecular nanocapsule 1·(BArF)₈ acts as a supramolecular mask and provides a two-fold enhancement up to 56% of equatorial e,e-bis-PCBM-C₆₀ adducts using semi-stabilised sulfur ylides as reagents. This strategy conforms to a rapid and straightforward methodology in comparison to the reported tedious multi-stage and multicolumn HPLC process in peak-recycling mode.

GRAPHICAL ABSTRACT

KEYWORDS:

• Fullerene
• regioselectivity
• PCBM-C60 bis-adduct isomers
• supramolecular mask

Acknowledgments

This work was supported by grants from MINECO-Spain (PID2019-104498GB-I00, PID2022-136970NB-I00, and TED2021-130573B-I00), Fundación Areces (RegioSolar project), and Generalitat de Catalunya AGAUR (2021SGR00475). M.P. thanks the IF-UdG PhD grant and V.I. thanks MINECO for the FPI grant. We thank the QBIS-CAT research group and STR-UdG for technical support. We are also grateful for the ICREA-Academia award to X.R.

Disclosure statement

No potential conflict of interest was reported by the author(s).

Supplementary material

Supplemental data for this article can be accessed online at https://doi.org/10.1080/10610278.2024.2338141

Additional information

Funding

This work was supported by the Ministerio de Ciencia e Innovación [PID2022-136970NB-I00], Fundación Areces (RegioSolar project) and Generalitat de Catalunya AGAUR (2021SGR00475).