Abstract

VILLADA, Juan D.; DUARTE-RUIZ, Álvaro  and  CHAUR, Manuel N.. Regiospecific synthesis and electrochemical study of two water-soluble C₆₀ carboxylic derivatives. Rev. acad. colomb. cienc. exact. fis. nat. [online]. 2021, vol.45, n.174, pp.272-285.  Epub Sep 18, 2021. ISSN 0370-3908.  https://doi.org/10.18257/raccefyn.1187.

We report a new methodology for the synthesis of two highly symmetric equatorial malonate hexaadducts of C60 fullerene. The synthetic methodology is based on a series of protection and deprotection steps that allow the preparation of a fullerene [60] functionalized with six symmetrical positioned malonate addends without using complicated and expensive separation techniques (high-performance liquid chromatography, HPLC) or long reaction times. This methodology allowed us to prepare the carboxylic adducts 6 (equatorial octacarboxylic tetraadduct of C60) and 8 (equatorial dodecacarboxylic hexakisadduct of C60). As far as we know, compound 6 has not yet been reported. We also studied the electronic properties of the main compounds by UV-Vis spectroscopy and cyclic voltammetry (CV). The reported fullerene adducts exhibited several reversible reduction processes whose electron transfers are controlled by diffusion.

Keywords : Fullerenes; Symmetric adducts; Bingel reaction; Cyclic voltammetry.

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