Facile fullerene modification: FeCl3-mediated quantitative conversion of C60 to polyarylated fullerenes containing pentaaryl(chloro)[60]fullerenes

Masahiko Hashiguchi; Kazuhiro Watanabe; Yutaka Matsuo

doi:10.1039/C1OB05895A

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Facile fullerene modification: FeCl₃-mediated quantitative conversion of C₆₀ to polyarylated fullerenes containing pentaaryl(chloro)[60]fullerenes†‡

Masahiko Hashiguchi,*^a Kazuhiro Watanabe^a and Yutaka Matsuo*^b

Author affiliations

* Corresponding authors

^a Fullerene Development Group, Performance Products Division, Mitsubishi Chemical Corporation, 1-1 Kurosakishiroishi, Yahatanishi-ku, Kitakyushu, Japan
E-mail: 6206530@cc.m-kagaku.co.jp
Fax: +81-93-643-4401

^b Department of Chemistry, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo, Japan
E-mail: matsuo@chem.s.u-tokyo.ac.jp
Fax: +81-3-5841-1476
Tel: +81-3-5841-1476

Abstract

A facile, one-step reaction using inexpensive reagents has been developed for functionalization of [60]fullerene, where the reaction of C₆₀ with FeCl₃ in chlorobenzene proceeded at 25 °C with 100% conversion, yielding a mixture of polyarylated products containing pentaaryl(chloro)[60]fullerene, C₆₀(C₆H₄Cl)₅Cl (up to 29%) and other polyarylated fullerenes (number of aryl groups is in a range from 5 to 10).

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Article information

DOI: https://doi.org/10.1039/C1OB05895A
Article type: Paper
Submitted: 04 Jun 2011
Accepted: 17 Jun 2011
First published: 01 Aug 2011

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Org. Biomol. Chem., 2011,9, 6417-6421

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Facile fullerene modification: FeCl₃-mediated quantitative conversion of C₆₀ to polyarylated fullerenes containing pentaaryl(chloro)[60]fullerenes

M. Hashiguchi, K. Watanabe and Y. Matsuo, Org. Biomol. Chem., 2011, 9, 6417 DOI: 10.1039/C1OB05895A

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Organic & Biomolecular Chemistry