TY - JOUR
T1 - Fullerene cation-mediated demethylation/cyclization to give 5- and 7-membered cyclo[60]fullerene derivatives
AU - Matsuo, Yutaka
AU - Ogumi, Keisuke
AU - Zhang, Ying
AU - Okada, Hiroshi
AU - Nakagawa, Takafumi
AU - Ueno, Hiroshi
AU - Gocho, Akiko
AU - Nakamura, Eiichi
N1 - Funding Information:
This work was supported by the start-up funding in University of Science and Technology of China, and partially supported by the Grants-in-Aid for Scientific Research (JSPS KAKENHI Grant Numbers JP15H05760 and JP16H04187), MEXT, Japan and the Strategic Promotion of Innovative Research and Development, Japan Science and Technology Agency (JST), Japan. This work is also based on results obtained from a project commissioned by the New Energy and Industrial Technology Development Organization (NEDO), Japan.
Publisher Copyright:
© The Royal Society of Chemistry.
PY - 2017
Y1 - 2017
N2 - Single-bonded fullerene dimers, (C60R)2 (R = (2-methoxyphenyl)dimethylsilylmethyl, (isopropoxy)dimethylsilylmethyl, and 2-methoxy-5-methylphenyl), afforded fullerene derivative cations (RC60+) in the presence of an oxidant (I2, CuCl2, or CuBr2), leading to 5- and 7-membered cyclo[60]fullerene derivatives such as cyclo[60]fullerenes containing a Si-O bond, cyclo[60]fullerenes containing a C60-O bond, and dihydrobenzofurano[60]fullerene. The reaction mechanism involved thermal homolytic cleavage to give fullerene radicals, oxidation of the radicals to generate fullerene cations, and then demethylative cyclization in which the fullerene cationic centers interact with an aromatic group or the oxygen atoms of methoxy groups to produce the cyclized products. The obtained cyclo[60]fullerene derivatives were used in bulk-heterojunction organic solar cells and showed moderate power conversion efficiency and respectable open-circuit voltage.
AB - Single-bonded fullerene dimers, (C60R)2 (R = (2-methoxyphenyl)dimethylsilylmethyl, (isopropoxy)dimethylsilylmethyl, and 2-methoxy-5-methylphenyl), afforded fullerene derivative cations (RC60+) in the presence of an oxidant (I2, CuCl2, or CuBr2), leading to 5- and 7-membered cyclo[60]fullerene derivatives such as cyclo[60]fullerenes containing a Si-O bond, cyclo[60]fullerenes containing a C60-O bond, and dihydrobenzofurano[60]fullerene. The reaction mechanism involved thermal homolytic cleavage to give fullerene radicals, oxidation of the radicals to generate fullerene cations, and then demethylative cyclization in which the fullerene cationic centers interact with an aromatic group or the oxygen atoms of methoxy groups to produce the cyclized products. The obtained cyclo[60]fullerene derivatives were used in bulk-heterojunction organic solar cells and showed moderate power conversion efficiency and respectable open-circuit voltage.
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U2 - 10.1039/c6ta10319g
DO - 10.1039/c6ta10319g
M3 - Article
AN - SCOPUS:85012014138
SN - 2050-7488
VL - 5
SP - 2774
EP - 2783
JO - Journal of Materials Chemistry A
JF - Journal of Materials Chemistry A
IS - 6
ER -
