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Functionalization of [60]fullerene through fullerene cation intermediates

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Abstract

Fullerene cations, namely [60]fullerene radical cation (C60˙+) and organo[60]fullerenyl cation (RC60+), are less investigated as intermediates in synthetic fullerene chemistry because of the intrinsic electronegativity of C60. Remarkably, these two intermediates can mediate reactions that afford versatile, unique and unexpected fullerene derivatives. This review article mainly describes these C60˙+ and RC60+ intermediates and includes a variety of topics, from the generation of C60˙+ and RC60+ species to their applications in fullerene modification reactions, such as Friedel–Crafts hydroarylation, nucleophilic addition, dimerization, intramolecular rearrangement reactions, and intramolecular cyclization reactions. Additionally, this review deeply discusses the mechanism of the formation of unique [60]fullerene derivatives involving [60]fullerene radical cation and organo[60]fullerenyl cation intermediates. In addition, the electrochemical properties and photovoltaic performance of these fullerene derivatives produced through C60˙+ or RC60+-mediated reactions are discussed in this review.

Graphical abstract: Functionalization of [60]fullerene through fullerene cation intermediates

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Publication details

The article was received on 23 Jul 2018, accepted on 28 Aug 2018 and first published on 01 Sep 2018


Article type: Feature Article
DOI: 10.1039/C8CC05965A
Citation: Chem. Commun., 2018, Advance Article
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    Functionalization of [60]fullerene through fullerene cation intermediates

    H. Lin and Y. Matsuo, Chem. Commun., 2018, Advance Article , DOI: 10.1039/C8CC05965A

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