The intermolecular anthracene-transfer in a regiospecific antipodal C₆₀ difunctionalization.

ABSTRACT: Ever since the discovery of fullerenes, their mono- and multi-functionalization by exohedral addition chemistry has been a fundamental topic. A few years ago, a topochemically controlled regiospecific difunctionalization of C₆₀ fullerene by anthracene in the solid state was discovered. In the present work, we analyse the mechanism of this unique reaction, where an anthracene molecule is transferred from one C₆₀ mono-adduct to another one, under exclusive formation of equal amounts of C₆₀ and of the difficult to make, highly useful, antipodal C₆₀ bis-adduct. Our herein disclosed dispersion corrected DFT studies show the anthracene transfer to take place in a synchronous retro Diels-Alder/Diels-Alder reaction: an anthracene molecule dissociates fro

SUBMITTER: Talmazan RA 

PROVIDER: S-EPMC7616903 | biostudies-literature | 2020 Jun

REPOSITORIES: biostudies-literature