High–yield reactive extraction of giant fullerenes from soot

Abstract

By the common Soxhlet extraction with 1,2,4-trichlorobenzene a mere 8 mass % of virgin fullerene soot can be dissolved. The extracted soot was subjected to a reactive extraction with 5-hexadecanamido-1,3-dihydro-2-benzothiophene 2,2-dioxide(4), an ortho-quinodimethane precursor. Through an irreversible Diels–Alder cycloaddition an additional 12 mass % was solubilized. Mass spectrometry, vapour pressure osmometry and elemental analysis indicate that the soluble material consists of multiple adducts of fullerenes C₆₀–C₄₁₈ .

References

1. H. W. Kroto, J. R. Heath, S. C. O'Brien, R. F. Curl and R. E. Smalley, Nature, 1985, 318, 162.
2. W. Krätschmer, K. Fostiropoulos and D. R. Huffman, Chem. Phys. Lett., 1990, 347, 167.
3. W. Krätschmer, L. D. Lamb, K. Fostiropoulos and D. R. Huffman, Nature, 1990, 347, 354.
4. H. Werner, D. Herein, J. Blöcker, B. Henschke, U. Tegtmeyer, T. Schedel-Niedrig, M. Keil, A. M. Bradshaw and R. Schlögl, Chem. Phys. Lett., 1992, 194, 62.
5. F. Diederich, R. Ettl, Y. Rubin, R. L. Whetten, R. Beck, M. Alvarez, S. Anz, D. Sens-harma, F. Wudl, K. C. Khemani and A. Koch, Science, 1992, 252, 548.
6. C. Smart, B. Eldridge, W. Reuter, J. A. Zimmerman, W. R. Creasy, N. Riviera and R. S. Ruoff, Chem. Phys. Lett., 1992, 188, 171.
7. W. R. Creasy, J. A. Zimmerman and R. S. Ruoff, J. Phys. Chem., 1993, 97, 973.
8. H. Shinohara, H. Sato, Y. Saito, M. Takayama, A. Izuoka and T. Sugawara, J. Phys. Chem., 1991, 95, 8449.
9. H. Shinohara, H. Sato, Y. Saito, A. Izuoka, T. Sugawara, H. Ito, T. Sakurai and T. Matsuo, Rapid Commun. Mass. Spectrom., 1992, 6, 413.
10. D. H. Parker, P. Wurz, K. Chatterjee, K. R. Lykke, J. E. Hunt, M. J. Pellin, J. C. Hemminger, D. M. Gruen and L. M. Stock, J. Am. Chem. Soc., 1991, 113, 7499.
11. D. H. Parker, K. Chatterjee, P. Wurz, K. L. Lykke, M. J. Pellin and L. M. Stock, Carbon, 1992, 30, 1167.
12. K. R. Lykke, D. H. Parker and P. Wurz, Int. J. Mass Spectrom. Ion Processes, 1994, 138, 147.
13. A. S. Hirschon, H. -J. Wu, R. B. Wilson and R. Malhotra, J. Phys. Chem., 1995, 99, 17483.
14. E. Schlichting, W. Halwachs and K. Schügerl, Chem. Eng. Commun., 1987, 51, 193.
15. Yi. -Zh. An, G. A. Ellis, A. L. Viado and Y. Rubin, J. Org. Chem., 1995, 60, 6353.
16. P. Belik, A. Gügel, J. Spickermann and K. Müllen, Angew. Chem., 1993, 105, 95; Angew. Chem., Int. Ed. Engl., 1993, 32, 78.
17. B. Illescas, N. Martin, C. Seoane, P. de la Cruz, F. Langa and F. Wudl, Tetrahedron Lett., 1995, 36, 8307.
18. J. M. Wood, B. Kahr, S. H. Hoke, L. Dejarme, R. G. Cooks and D. Ben-Amotz, J. Am. Chem. Soc., 1991, 113, 5907.
19. A. M. Vasallo, L. S. K. Pang, P. A. Cole-Clarke and M. A. Wilson, J. Am. Chem. Soc., 1991, 113, 7820.
20. F. H. Hennrich, R. H. Michel, A. Fischer, S. Richard-Schneider, S. Gilb, M. M. Kappes, D. Fuchs, M. Bürk, K. Kobayashi and S. Nagase, Angew. Chem., 1996, 108, 1839.
21. A. Gügel, A. Kraus, J. Spickermann, P. Belik and K. Müllen, Angew. Chem., 1994, 106, 601; Angew. Chem., Int. Ed. Engl., 1994, 33, 559.
22. M. P. Cava and A. A. Deana, J. Am. Chem. Soc., 1959, 81, 4266.
23. M. Walter, A. Gügel, J. Spickermann, P. Belik, A. Kraus and K. Müllen, Fullerene Sci. Technol., 1996, 4, 101.