@article{73224dbb08ed4d49bf9a499ef1fa318a,
title = "Highly soluble: C 2v-symmetrical fullerene derivatives: Efficient synthesis, characterization, and electrochemical study",
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.",
author = "Yue Ma and Kouya Uchiyama and Hiroshi Ueno and Hiroshi Okada and Hiroshi Moriyama and Yutaka Matsuo",
note = "Funding Information: This work was supported by the thousand talent program in Northeast Normal University. This work was also partly sup- ported by the Bilateral International Collaborative R&D Program (Project number: 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 HM), and Japan Society for the Promotion of Science (JSPS) KAKENHI Grants (No. JP15H05760 to YM). Computational studies were performed using Research Center for Computational Science, Okazaki, Japan. Publisher Copyright: {\textcopyright} 2019 the Partner Organisations.",
year = "2019",
month = may,
day = "7",
doi = "10.1039/c9qo00056a",
language = "English",
volume = "6",
pages = "1372--1377",
journal = "Organic Chemistry Frontiers",
issn = "2052-4110",
publisher = "Royal Society of Chemistry",
number = "9",
}