Octaalkoxyfullerenes: Widely LUMO-Tunable C2 v-Symmetric Fullerene Derivatives

Hiroshi Ueno; Kouya Uchiyama; Yue Ma; Keita Watanabe; Kenji Yoza; Yutaka Matsuo; Hiroshi Moriyama

doi:10.1021/acs.joc.8b01485

Octaalkoxyfullerenes: Widely LUMO-Tunable C_{2 v}-Symmetric Fullerene Derivatives

Hiroshi Ueno, Kouya Uchiyama, Yue Ma, Keita Watanabe, Kenji Yoza, Yutaka Matsuo, Hiroshi Moriyama

Research output: Contribution to journal › Article › peer-review

5 Citations (Scopus)

Abstract

C_2v-Symmetric octaalkoxyfullerenes, C₆₀(OR)₈ (R = CH₃, C₂H₅, CH₂CF₃), were synthesized by reacting octabromofullerene with the corresponding alcohols in the presence of AgBF₄. The reactions occurred with no change in the addition pattern, and the compounds were unambiguously characterized by NMR spectroscopy and X-ray structure analysis. Electrochemical measurements revealed not only that these derivatives have stable redox properties but also that their LUMO levels can be tuned over a very wide range.

Original language	English
Pages (from-to)	10655-10659
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	83
Issue number	17
DOIs	https://doi.org/10.1021/acs.joc.8b01485
Publication status	Published - 2018 Sep 7
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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title = "Octaalkoxyfullerenes: Widely LUMO-Tunable C2 v-Symmetric Fullerene Derivatives",

abstract = "C2v-Symmetric octaalkoxyfullerenes, C60(OR)8 (R = CH3, C2H5, CH2CF3), were synthesized by reacting octabromofullerene with the corresponding alcohols in the presence of AgBF4. The reactions occurred with no change in the addition pattern, and the compounds were unambiguously characterized by NMR spectroscopy and X-ray structure analysis. Electrochemical measurements revealed not only that these derivatives have stable redox properties but also that their LUMO levels can be tuned over a very wide range.",

author = "Hiroshi Ueno and Kouya Uchiyama and Yue Ma and Keita Watanabe and Kenji Yoza and Yutaka Matsuo and Hiroshi Moriyama",

note = "Funding Information: This work was partly supported by the Bilateral International Collaborative R&D Program (GT-2009-CL-OT-0058), Ministry of Knowledge Economy, Republic of Korea and the MEXT-Supported Program for the Strategic Research Foundation at Private Universities, Japan (to H.M.) and Japan Society for the Promotion of Science (JSPS) KAKENHI Grants (JP15H05760 and JP16H04187, to Y.M.). Publisher Copyright: Copyright {\textcopyright} 2018 American Chemical Society.",

year = "2018",

month = sep,

day = "7",

doi = "10.1021/acs.joc.8b01485",

language = "English",

volume = "83",

pages = "10655--10659",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "17",

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T1 - Octaalkoxyfullerenes

T2 - Widely LUMO-Tunable C2 v-Symmetric Fullerene Derivatives

AU - Ueno, Hiroshi

AU - Uchiyama, Kouya

AU - Ma, Yue

AU - Watanabe, Keita

AU - Yoza, Kenji

AU - Matsuo, Yutaka

AU - Moriyama, Hiroshi

N1 - Funding Information: This work was partly supported by the Bilateral International Collaborative R&D Program (GT-2009-CL-OT-0058), Ministry of Knowledge Economy, Republic of Korea and the MEXT-Supported Program for the Strategic Research Foundation at Private Universities, Japan (to H.M.) and Japan Society for the Promotion of Science (JSPS) KAKENHI Grants (JP15H05760 and JP16H04187, to Y.M.). Publisher Copyright: Copyright © 2018 American Chemical Society.

PY - 2018/9/7

Y1 - 2018/9/7

N2 - C2v-Symmetric octaalkoxyfullerenes, C60(OR)8 (R = CH3, C2H5, CH2CF3), were synthesized by reacting octabromofullerene with the corresponding alcohols in the presence of AgBF4. The reactions occurred with no change in the addition pattern, and the compounds were unambiguously characterized by NMR spectroscopy and X-ray structure analysis. Electrochemical measurements revealed not only that these derivatives have stable redox properties but also that their LUMO levels can be tuned over a very wide range.

AB - C2v-Symmetric octaalkoxyfullerenes, C60(OR)8 (R = CH3, C2H5, CH2CF3), were synthesized by reacting octabromofullerene with the corresponding alcohols in the presence of AgBF4. The reactions occurred with no change in the addition pattern, and the compounds were unambiguously characterized by NMR spectroscopy and X-ray structure analysis. Electrochemical measurements revealed not only that these derivatives have stable redox properties but also that their LUMO levels can be tuned over a very wide range.

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ER -

Octaalkoxyfullerenes: Widely LUMO-Tunable C_{2 v}-Symmetric Fullerene Derivatives

Abstract

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