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Issue 9, 2019
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Highly soluble C2v-symmetrical fullerene derivatives: efficient synthesis, characterization, and electrochemical study

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Abstract

Through an efficient octa-substitution reaction, octabromofullerene (C60Br8) was reacted with alcohols or anisole in the presence of silver triflate to produce octaalkoxy and octaaryl fullerenes, respectively, in up to 79% yield with retention of C2v-symmetry. The LUMO level could be widely tuned through the cumulative substituent effects of the eight addends. The difference in LUMO energy level between C60(OCH2CCl3)8 and C60(C6H4-OMe-4)8 was 0.53 eV, representing low-LUMO and high-LUMO fullerenes. Dynamic light scattering measurements revealed that these octa-substituted compounds were dispersed as single molecules both in toluene and in dichloromethane under low-concentration condition. This lack of aggregate formation is attributed to the polar and non-polar hemispheres of these molecules.

Graphical abstract: Highly soluble C2v-symmetrical fullerene derivatives: efficient synthesis, characterization, and electrochemical study

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The article was received on 12 Jan 2019, accepted on 04 Feb 2019 and first published on 05 Feb 2019


Article type: Research Article
DOI: 10.1039/C9QO00056A
Org. Chem. Front., 2019,6, 1372-1377

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    Highly soluble C2v-symmetrical fullerene derivatives: efficient synthesis, characterization, and electrochemical study

    Y. Ma, K. Uchiyama, H. Ueno, H. Okada, H. Moriyama and Y. Matsuo, Org. Chem. Front., 2019, 6, 1372
    DOI: 10.1039/C9QO00056A

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