Hostname: page-component-8448b6f56d-m8qmq Total loading time: 0 Render date: 2024-04-16T23:25:36.335Z Has data issue: false hasContentIssue false
  • English
  • Français

Functionalizing C60 via Nucleophilic Trapping of its Radical Cations: 1. Alkoxylation and Arylation of C60; 2. Synthesis of Earmuff Ethers (Difulleroxyalkanes)

Published online by Cambridge University Press:  25 February 2011

Glen P. Miller ,
Chang S. Hsu ,
Hans Thomann ,
Long Y. Chiang  and
Marcelino Bernardo
Glen P. Miller
Affiliation:
Corporate Research Laboratories, Exxon Research & Engineering Company, Annandale, N.J. 08801
Chang S. Hsu
Affiliation:
Corporate Research Laboratories, Exxon Research & Engineering Company, Annandale, N.J. 08801
Hans Thomann
Affiliation:
Corporate Research Laboratories, Exxon Research & Engineering Company, Annandale, N.J. 08801
Long Y. Chiang
Affiliation:
Corporate Research Laboratories, Exxon Research & Engineering Company, Annandale, N.J. 08801
Marcelino Bernardo
Affiliation:
Corporate Research Laboratories, Exxon Research & Engineering Company, Annandale, N.J. 08801
Get access

Abstract

While its electrochemical oxidation is difficult, Cgg is readily oxidized in protic superacidic media. In order to exploit the reactive nature of the radical cations thus formed for the purpose of generating novel fullerene derivatives, a method involving nucleophilic trapping of oxidized Cgg has been developed. Thus, trapping oxidized Cgg with alcohols and aromatics results in the formation of alkoxylated and arylated C60, respectively, while trapping oxidized CgQ with x, y-diols results in the formation of x, y-difulleroxyalkanes (earmuff ethers).

Type
Research Article
Information
MRS Online Proceedings Library (OPL) , Volume 247: Symposium N – Electrical, Optical, and Magnetic Properties of Organic Solid State Materials , 1992 , 293
Copyright
Copyright © Materials Research Society 1992

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

1. Kratschmer, W., Fostiropoulos, K., and Huffman, D.R., Chem. Phys. Lett. 170. 167(1990);Google Scholar
Kratschmer, W., Lamb, L., Fostiropoulos, K., and Huffman, D.R., Nature 347. 354(1990).Google Scholar
2. Haddon, R.C., Brus, L.E., and Raghavachari, K., Chem. Phys. Lett. 125, 459 (1986).Google Scholar
3. Dubois, D., Kadish, K.M., Flanagan, S., Haufler, R.E., Chibante, L.P.F., and Wilson, L., J. Am. Chem. Soc. 113, 4364 (1991);Google Scholar
Kadish, K.M., Dubois, D., Flanagan, S., and Wilson, L.J., J. Am. Chem. Soc. 113, 7773 (1991).Google Scholar
4. Allemand, P.M., Koch, A., Wudl, F., Rubin, Y., Diederich, F., Alvarez, M.M., Anz, S.J., and Whetten, R.L. J. Am. Chem. Soc. 113, 1050 (1991).Google Scholar
5. Cox, D.M., Behal, S., Disko, M., Gorun, S.M., Greaney, M.A., Hsu, C.S., Kollin, E., Millar, J., Robbins, J., Robbins, W., Sherwood, R.D., and Tindall, P., J. Am. Chem. Soc. 113, 2940 (1991).Google Scholar
6. Greaney, M.A. and Gorun, S.M., J. Phys. Chem. 95, 7142 (1991).Google Scholar
7. Haufler, R.E., Conceicao, J., Chibante, L.P.F., Chai, Y., Byrne, N.E., Flanagan, S., Haley, M.M., O'Brien, S.C., Pan, C., Xiao, Z., Billups, W.E., Ciufolini, M.A., Hauge, R.H., Margrave, J.L., Wilson, L.J., Curl, R.F., and Smalley, R.E., J. Phys. Chem. 94, 8634 (1990).Google Scholar
8. Bausch, J.W., Prakash, G.K.S., Olah, G.A., Tse, D.S., Lorents, D.C., Bae, Y.K., and Malhotra, R., J. Am. Chem. Soc. 113, 3205 (1991).Google Scholar
9. Bard, A.J., Ledwith, A., and Shine, H.J. in Adv. Phys. Org. Chem., edited by Gold, V. and Bethell, D. (Academic Press, New York, 1976), p. 157.Google Scholar
10. Miller, G., presented at the Conference on Fullerenes and Fullerites, University Of Pennsylvania, August 2, 1991. 11.Google Scholar
Kukolich, S.G. and Huffman, D.R., Chem. Phys. Lett. 182, 263 (1991).Google Scholar
12. Kato, T., Kodama, T., Shida, T., Nakagawa, T., Matsui, Y., Suzuki, S., Shiromaru, H., Yamauchi, K., Achiba, Y., Chem. Phys. Lett. 182, 446 (1991).Google Scholar
13. While the absolute value of the spin counts is subject to considerable error (e.g., +/- 50%), the internal consistency of successive measurements is excellent. Thus, the overall trend in Figure lb fully supports the conclusions drawn in the text.Google Scholar
14. Parker, V.D., Dirlan, J.P., and Eberson, L., Acta. Chem. Scand. 25, 341 (1971).Google Scholar
15. Sioda, R.E., J. Phys. Chem. 72, 2322 (1968).Google Scholar
16. Blount, H.N. and Kuwana, T., J. Electroanal. Chem. 27, 464 (1970).Google Scholar