Hostname: page-component-586b7cd67f-l7hp2 Total loading time: 0 Render date: 2024-11-23T09:19:32.417Z Has data issue: false hasContentIssue false
  • English
  • Français

Synthesis of a New Class of Molecule Li+@C60O–(OH)7 as a “Cation-Encapsulated Anion Nanoparticle” by Multihydroxylation of Li-Encapsulated Fullerene

Published online by Cambridge University Press:  27 February 2013

Hiroshi Ueno ,
Yuji Nakamura ,
Naohiko Ikuma ,
Ken Kokubo  and
Takumi Oshima
Hiroshi Ueno
Affiliation:
Division of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871, Japan
Yuji Nakamura
Affiliation:
Division of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871, Japan
Naohiko Ikuma
Affiliation:
Division of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871, Japan
Ken Kokubo*
Affiliation:
Division of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871, Japan
Takumi Oshima
Affiliation:
Division of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871, Japan
*
*Email: [email protected]
Get access

Abstract

Treatment of [Li+@C60](PF6–) with 30% fuming sulfuric acid and subsequent hydrolysis gave hydroxylated derivative Li+@C60O–(OH)7. Its structure was deduced by IR, NMR, MALDI-TOF/FAB MS, and elemental analysis. Notably, the reaction of [Li+@C60](PF6–) was site-selective, giving a single major isomer (ca. 70%) with two minor isomers, in marked contrast to the case of empty C60. Furthermore, the results clearly indicate that the internal Li cation was strongly shielded by the surface dipolar hydroxyl groups, and thus it appears that the properties of endohedral fullerenes can be controlled by the external modification of the fullerene cage. Whereas Li+@C60 is relatively insoluble, Li+@C60O–(OH)7 was found to be highly soluble in polar solvents such as DMSO and DMF. The increased solubility is especially desirable for biological/medicinal assays and applications in such research fields.

Keywords

Liorganicreactivity
Type
Articles
Information
MRS Online Proceedings Library (OPL) , Volume 1505: Symposium W – Carbon Nanomaterials , 2013 , mrsf12-1505-w17-32
Copyright
Copyright © Materials Research Society 2013

Access options

Get access to the full version of this content by using one of the access options below. (Log in options will check for institutional or personal access. Content may require purchase if you do not have access.)

References

REFERENCES

Aoyagi, S., Nishibori, E., Sawa, H., Sugimoto, K., Takata, M., Miyata, Y., Kitaura, R., Shinohara, H., Okada, H., Sakai, T., Ono, Y., Kawachi, K., Yokoo, K., Ono, S., Omote, K., Kasama, Y., Ishikawa, S., Komuro, T., Tobita, H., Nature Chem. 2, 678–683 (2010).CrossRefGoogle Scholar
Fukuzumi, S., Ohkubo, K., Kawashima, Y., Kim, D. S., Park, J. S., Jana, A., Lynch, V. M., Kim, D., Sessler, J. L., J. Am. Chem. Soc. 133, 15938–15941 (2011).CrossRefGoogle Scholar
Matsuo, Y., Okada, H., Maruyama, M., Sato, H., Tobita, H., Ono, Y., Omote, K., Kawachi, K., Kasama, Y., Org. Lett. 14, 3784–3787 (2012).CrossRefGoogle Scholar
Aoshima, H., Kokubo, K., Shirakawa, S., Ito, M., Yamana, S., Oshima, T., Biocontrol Sci. 14, 69–72 (2009).CrossRefGoogle Scholar
Saitoh, Y., Mizuno, H., Xiao, L., Hyoudou, S., Kokubo, K., Miwa, N., Mol. Cell. Biochem. 366, 191–200 (2012).CrossRefGoogle Scholar
Chen, Z., Ma, L., Liu, Y., Chen, C., Theranostics 2, 238–250 (2012).CrossRefGoogle ScholarPubMed
Ueno, H., Nakamura, Y., Ikuma, N., Kokubo, K., Oshima, T., Nano Res. 6, 558–564 (2012).CrossRefGoogle Scholar
Chiang, L. Y., Wang, L. –Y., Swirczewski, J. W., Soled, S., Cameron, S., J. Org. Chem. 59, 3960–3968 (1994).CrossRefGoogle Scholar
Wada, Y., Totoki, S., Watanabe, M., Moriya, N., Tsunazawa, Y., Shimaoka, H., Opt. Express 14, 5755–5776 (2006).CrossRefGoogle Scholar