Skip to main content

Thank you for visiting nature.com. You are using a browser version with limited support for CSS. To obtain the best experience, we recommend you use a more up to date browser (or turn off compatibility mode in Internet Explorer). In the meantime, to ensure continued support, we are displaying the site without styles and JavaScript.

The chemistry of fullerenes

Abstract

Initially envisaged as rather unreactive, aromatic-like molecules, the fullerenes instead undergo a wide variety of reactions characteristic of alkenes. The many derivatives of C60, and the few of C70, that have now been reported offer new directions for organic chemistry.

This is a preview of subscription content, access via your institution

Relevant articles

Open Access articles citing this article.

Access options

Buy article

Get time limited or full article access on ReadCube.

$32.00

All prices are NET prices.

References

  1. Krätschmer, W., Lamb, L. D., Fostiropoulos, K. & Huffman, D. R. Nature 347, 354–358 (1990).

    ADS  Google Scholar 

  2. Taylor, R., Hare, J. P., Abdul-Sada, A. K. & Kroto, H. W. J. chem. Soc. chem. Commun., 1423–1425 (1990)

  3. Taylor, R. Interdisciplinary Sci. Rev. 17, 161–170 (1992).

    Google Scholar 

  4. Iijima, S. Nature 356, 776–778; 358, 220–222 (1992).

    ADS  CAS  Google Scholar 

  5. Kroto, H. W., Heath, J. R., O'Brien, S. C., Curl, R. F. & Smalley, R. E. Nature 318, 162–163 (1985).

    Article  ADS  CAS  Google Scholar 

  6. Klein, D. J., Schmalz, T. G., Hite, T. G. & Seitz, W. A. J. Am. chem. Soc. 108, 1301–1302 (1986).

    CAS  Google Scholar 

  7. Mills, W. H. & Nixon, I. G. J. chem. Soc., 2510–2524 (1930).

    CAS  Google Scholar 

  8. Taylor, R. Electrophilic Aromatic Substitution, 53–55 (Wiley, Chichester, 1989).

    Google Scholar 

  9. Taylor, R. Tetrahedron Lett., 3731–3734 (1991); J. chem. Soc., Perkin Trans. 2, 3–4 (1992).

    Google Scholar 

  10. Schmaltz, T. G., Seitz, W. A., Klein, D. J. & Hite, T. G. J. Am. chem. Soc. 110, 1113–1127 (1988).

    Google Scholar 

  11. Bent, H. A. Chem. Ref. 61, 275–311 (1961).

    CAS  Google Scholar 

  12. Anacleto, J. F. et al. Rapid Commun. Mass Spectrom. 6, 214–220 (1992); Rapid Commun. Mass Spectrom. (in the press).

    ADS  CAS  PubMed  Google Scholar 

  13. Hawkins, J. M. et al. J. Am. chem. Soc 114, 7954–7955 (1992).

    CAS  Google Scholar 

  14. Taylor, R. et al. Nature 351, 277 (1991).

    ADS  CAS  Google Scholar 

  15. Kawata, S. et al. Chem. Lett., 1659–1662 (1992).

    Google Scholar 

  16. Werner, H. et al. Angew. Chem. int. Edn. Engl. 31, 868–870 (1992).

    Google Scholar 

  17. Scrivens, W. A. Bedworth, P. V. & Tour, J. M. J. Am. chem. Soc. 114, 7917–7919 (1992).

    CAS  Google Scholar 

  18. Gevaert, M. & Kamat, P. V. J. chem. Soc. chem. Commun., 1470–1472 (1992).

  19. Gilmour, I. et al. Lunar planet. Sci. Conf. XXII, 445–446 (1991).

  20. Chen, H. S., Kortan, A. R., Haddon, R. C. & Fleming, D. A. J. Phys. Chem. 96, 1016–1018 (1992).

    CAS  Google Scholar 

  21. Tycko, R. et al. J. phys. Chem. 95, 518–520 (1991).

    CAS  Google Scholar 

  22. Yannoni, C. S., Johnson, R. D. Meijer, G., Bethune, D. S. & Salem, J. R. J. phys. Chem. 95, 9–10 (1991).

    CAS  Google Scholar 

  23. Meidine, M. F., Hitchcock, P. B., Kroto, H. W., Taylor, R. & Walton, D. R. M. J. chem. Soc. chem. Commun., 1534–1537 (1992).

  24. Balch, A. L., Lee, J. W., Noll, B. C. & Olmstead, M. M. J. chem. Soc. chem. Commun., 56–58 (1993).

  25. Geiser, U. et al. Chem. Mater. 4, 1077–1082 (1992).

    CAS  Google Scholar 

  26. Gorun, S. M. et al. J. chem. Soc chem. Commun., 1556–1558 (1991).

  27. Balch, A. L., Catalano, J. C. & Lee, J. Inorg. Chem. 21, 3980–3981 (1991).

    Google Scholar 

  28. Balch, A. L., Catalano, V. J., Lee, J. W., Olmstead, M. M. & Parkin, S. R. J. Am. chem. Soc. 113, 8953–8955 (1991).

    CAS  Google Scholar 

  29. Hawkins, J. M., Meyer, A., Lewis, T. A., Loren, S. & Hollander, F. J. Science 252, 312–314 (1991).

    ADS  CAS  PubMed  Google Scholar 

  30. Fagan, P. J., Calabrese, J. C. & Malone, B. Science 252, 1160–1161 (1991).

    ADS  CAS  Google Scholar 

  31. Balch, A. L., Catalano, V. J., Lee, J. W. & Olmstead, M. M. J. Am. chem. Soc. 114, 5455–5457 (1992).

    CAS  Google Scholar 

  32. Andersson T., Nilsson, K., Sundahl, M., Westman, G. & Wennerström, O. J. chem. Soc. chem. Commun., 604–605 (1992).

  33. Kuthner, W., Boulas, P. & Kadish, K. M. J. electrochem. Soc. 139, 243C (1992).

    Google Scholar 

  34. Ermer, O. Helv. chim. Acta 74, 1339–1351 (1991).

    CAS  Google Scholar 

  35. Izuoka, A. et al. J. chem. Soc. Chem. Commun., 1472–1473 (1992).

  36. Crane, J. D., Hitchcock, P. W., Kroto, H. W., Taylor, R. & Walton, D. R. M. J. chem. Soc. chem. Commun., 1764–1765 (1992).

  37. Roth, G. & Adelmann, P. J. Phys. I France 2, 1541–1548 (1992); Appl. Phys. A56 (in the press).

    CAS  Google Scholar 

  38. Ohsawa, Y. & Saji, T. J. chem. Soc chem. Commun., 781–782 (1992).

  39. Xie, Q., Perez-Cordero, E. & Echegoyen, L. J. Am. chem. Soc. 114, 3978–3980 (1992).

    CAS  Google Scholar 

  40. Zhou, F., Jehoulet, C. & Bard, A. J. J. Am. chem. Soc. 114, 11004–11006 (1992).

    CAS  Google Scholar 

  41. Wudl, F. Accts. chem. Res. 25, 106–112 (1992).

    Google Scholar 

  42. Taylor, R. J. chem. Soc. Perkin Trans. 2, 1667–1669 (1992).

    Google Scholar 

  43. Kikuchi, K. et al. Nature 357, 142–144 (1992).

    ADS  CAS  Google Scholar 

  44. Manolopoulos, D. E., Fowler, P. W., Taylor, R., Kroto, H. W. & Walton, D. R. M. J. chem. Soc. Faraday Trans. 88, 1289–1290 (1992).

    Google Scholar 

  45. Taylor, R., et al. J. chem. Soc. Perkin Trans. 2, 1029–1036 (1993).

    Google Scholar 

  46. Meier, M. S., Guarr, T. F., Selegue, J. P. & Vance, V. K. J. chem. Soc. chem. Commun., 63–65 (1993).

  47. Darwish, A., Kroto, H. W., Taylor, R. & Walton, D. R. M. Fullerene Sci. Technol. (submitted).

  48. Haufler, R. E. et al. J. phys. Chem. 94, 8634–8636 (1990).

    CAS  Google Scholar 

  49. Malhotra, R., Tse, D. S., Ruoff, R. S., McMillen, D. F. & Lorent, D. C. J. electrochem. Soc. 139, 239C (1992).

    Google Scholar 

  50. Henderson, C. C. & Cahill, P. A. Science 259, 1885–1887 (1993).

    ADS  CAS  PubMed  Google Scholar 

  51. Lerke, S. A. Parkinson, B. A., Evans, D. H. & Fagan, P. J. J. Am. chem. Soc. 114, 7807–7813 (1992).

    CAS  Google Scholar 

  52. Li, Q., Wudl, F., Thilgen, C., Whetten, R. W. & Diederich, F. J. Am. chem. Soc. 114, 3994–3996 (1992).

    CAS  Google Scholar 

  53. Bausch, J. W. et al. J. Am. chem. Soc. 113, 3205–3206 (1991).

    CAS  Google Scholar 

  54. Hirsch, A., Soi, A. & Karfunkel, H. R. Angew. Chem. int. Edn. Engl. 31, 766–768 (1992).

    Google Scholar 

  55. Fagan, P. J., Krusic, P. J., Evans, D. H., Lerke, S. A. & Johnston, E. J. Am. chem. Soc 114, 9697–9699 (1992).

    CAS  Google Scholar 

  56. Taylor, R. J. chem. Soc Perkin Trans. 2, 813–824 (1993).

    Google Scholar 

  57. Taylor, R. et al. J. chem. Soc. chem. Commun., 665–667 (1992).

  58. Fowler, P. W., Kroto, H. W., Taylor, R. & Walton D. R. M. J. chem. Soc. Faraday Trans. 87, 2685–2686 (1992).

    Google Scholar 

  59. Scuseria, G. E. & Odom, G. K. Chem. Phys., Lett. 195, 531–533 (1992).

    ADS  CAS  Google Scholar 

  60. Meidine, M. F., et al. J. chem. Soc. chem. Commun. (in press).

  61. Rubin, Y., Khan, S., Freedberg, D. I. & Yeretzian, C. J. Am. chem. Soc, 115, 344–345 (1993).

    CAS  Google Scholar 

  62. Belik, P., Gügel, A., Spickerman, J. & Müllen, K. Angew. chem. int. Edn Engl. 32, 78–79 (1993).

    Google Scholar 

  63. Hoke, S. H. et al. J. org. Chem. 57, 5069–5071 (1992).

    CAS  Google Scholar 

  64. Tsuda, M., Ishida, T., Nogami, T., Kurono, S. & Ohashi, M. Chem. Lett., 2333–2334 (1992).

    Google Scholar 

  65. Taylor, R. Electrophilic Aromatic Substitution, 77, 145, 150 (Wiley, 1989).

    Google Scholar 

  66. Zhou, P., Dong, Z. H., Rao, A. M. & Eklund, P. C. Science, submitted.

  67. Yeretzian, C., Hansen, K., Diederich, F. & Whetten, R. L. Nature 359, 44–46 (1992).

    ADS  CAS  Google Scholar 

  68. Wood, J. M., et al. J. Am. chem. Soc. 113, 5907–5908 (1991).

    CAS  Google Scholar 

  69. Kalsbeck W. A. & Thorp, H. W. J. electroanal. Chem. 314, 363–365 (1991).

    CAS  Google Scholar 

  70. Diederich, F. et al. Science 252, 548–549 (1991).

    ADS  CAS  PubMed  Google Scholar 

  71. Taylor, R. et al. J. chem. Soc. chem. Commun., 667–668 (1992).

  72. Tuinman, A. A., Mukherjee, P., Adcock, J. L., Hettich, R. L. & Compton, R. N. J. phys. Chem. 96, 7584–7589 (1992).

    CAS  Google Scholar 

  73. Creegan, K. M. et al. J. Am. chem. Soc. 114, 1103–1105 (1992).

    CAS  Google Scholar 

  74. Elemes, Y. et al. Angew. Chem. int. Edn. Engl. 31, 351–353 (1992).

    Google Scholar 

  75. Arbogast, J. W. et al. J. Phys. Chem. 95, 11–12 (1991).

    CAS  Google Scholar 

  76. Taylor, R. et al. J. chem. Soc. chem. Commun. 875–878 (1993).

  77. Raghavachari, K. Chem. Phys. Lett. 195, 221–224 (1992).

    ADS  CAS  Google Scholar 

  78. Raghavachari, K. & Rohlfing, C. M. Chem. Phys. Lett. 97, 495–498 (1992).

    ADS  Google Scholar 

  79. Suzuki, T., Li, Q., Khemani, K. C., Wudl, F. & Almarsson, Ö. Science 254, 1186–1188 (1991).

    ADS  CAS  PubMed  Google Scholar 

  80. Suzuki, T., Li, Q., Khemani, K. C., Wudl, F. & Almarsson, Ö. J. Am. chem. Soc. 114, 7300–7301 (1992).

    CAS  Google Scholar 

  81. Suzuki, T., Li, Q., Khemani, K. C. & Wudl, F. J. Am. chem. Soc. 7301–7302 (1992).

    CAS  Google Scholar 

  82. Vasella, A., Uhlmann, P., Waldruff, C. A. A., Diederich, F. & Thilgen, C. Angew Chem. int. Edn Engl. 31, 1388–1390 (1992).

    Google Scholar 

  83. Fagan, P. J., Calabrese, J. C. & Malone, B. Accts chem. Res. 25, 134–142 (1992).

    CAS  Google Scholar 

  84. Koefod, R. S., Hudgens, M. F. & Shapley, J. R. J. Am. chem. Soc. 113, 8957–8958 (1991).

    CAS  Google Scholar 

  85. Balch, A. L., Lee, J. W., Noll, B. C. & Olmstead, M. M. J. Am. chem. Soc. 114, 10984–10985 (1992).

    CAS  Google Scholar 

  86. Balch, A. L., Lee, J. W. & Olmstead, M. M. Angew. Chem. int. Edn Engl. 31, 1356 (1992).

    Google Scholar 

  87. Hawkins, J. M., et al. J. org. Chem. 55, 6250–6252 (1990).

    CAS  PubMed  Google Scholar 

  88. Tebbe, F. N., et al. J. Am. chem. Soc. 113, 9900–9901 (1991).

    CAS  Google Scholar 

  89. Olah, G. A., et al. J. Am. chem. Soc. 113, 9385–9387 (1991).

    CAS  Google Scholar 

  90. Birkett, P. R., Hitchcock, P. W., Kroto, H. W., Taylor, R. & Walton, D. R. M. Nature 357, 479–481 (1992).

    ADS  CAS  Google Scholar 

  91. Tebbe, F. N. et al. Science 256, 822–825 (1992).

    ADS  CAS  PubMed  Google Scholar 

  92. Birkett, P. R. et al. J. chem. Soc. chem. Commun. (in press).

  93. Holloway, J. H. et al. J. chem. Soc. chem. Commun., 966–969 (1991).

  94. Selig, H. et al. J. Am. chem. Soc. 113, 5475–5476 (1991).

    CAS  Google Scholar 

  95. Kniaz, K. et al. J. Am. chem. Soc. (submitted).

  96. March, J. Advanced Organic Chemistry, 707–708 (Wiley, Chichester, 1992).

    Google Scholar 

  97. Wudl, F. et al. Am. chem. Soc. Symp. Series 481, 161–175 (1991).

    Google Scholar 

  98. Hirsch, A., Li, Q. & Wudl, F. Angew. Chem. int. Edn Engl. 30, 1309–1310 (1992).

    Google Scholar 

  99. Miller, G. P., Millar, J. M., Liang, B., Uldrich, S. & Johnston, J. E. J. chem. Soc. chem. Commun. 897–899 (1993).

    CAS  Google Scholar 

  100. Hoke, S. H. et al. Rapid Commun. Mass Spectrom. 5, 472–474 (1991).

    ADS  CAS  Google Scholar 

  101. Chiang, L. Y. et al. J. chem. Soc. chem. Commun., 1791–1793 (1992).

  102. Chiang, L. Y. Upasani, R. B. & Swirczewski, J. W. J. Am. chem. Soc. 114, 10154–10157 (1992).

    CAS  Google Scholar 

  103. Krusic, P. J. et al. J. Am. chem. Soc. 113, 6274–6275 (1991).

    CAS  Google Scholar 

  104. Morton, J. R., Preston, K. F., Krusic, P. J. & Wasserman, E. J. chem. Soc. Perkin Trans. 2, 1425–1429 (1992).

    Google Scholar 

  105. Krusic, P. J., Wasserman, E., Keizer, P. N., Morton, J. R. & Preston, K. F. Science 254, 1183–1185 (1991).

    ADS  CAS  PubMed  Google Scholar 

  106. Taylor, R. Electrophilic Aromatic Substitution, 15–18 (Wiley, Chichester, 1989).

    Google Scholar 

  107. Morton, J. R., Preston, K. F., Krusic, P. J., Hill, S. A. & Wasserman, E. J. phys. Chem. 96, 3576–3578 (1992): J. Am. chem. Soc. 114, 5454–5456 (1992).

    CAS  Google Scholar 

  108. Keizer, P. N., Morton, J. R. & Preston, K. F. chem. Soc. chem. Commun., 1259–1261 (1992).

  109. Taylor, R. et al. Nature 355, 27–28 (1992).

    ADS  Google Scholar 

  110. Amato, I. Science 254, 30–31 (1991).

    ADS  CAS  PubMed  Google Scholar 

  111. Loy, D. A. & Assink, R. A. J. Am. chem. Soc. 114, 3977–3978 (1992).

    CAS  Google Scholar 

  112. Samulski, E. T. et al. Chem. Mater. 4, 1153–1157 (1992).

    CAS  Google Scholar 

  113. Nagashima, H. et al. J. chem. Soc. chem. Commun., 377–379 (1992).

  114. Tutt, L. W. & Kost, A. Nature 356, 225–226 (1992).

    ADS  CAS  Google Scholar 

  115. Wang, Y. Nature 356, 585–587 (1992).

    ADS  CAS  Google Scholar 

  116. Loutfy, R. O. & Withers, J. C. Abstract 2145. Electrochem. Soc. Meeting, Hawaii (1993).

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Taylor, R., Walton, D. The chemistry of fullerenes. Nature 363, 685–693 (1993). https://doi.org/10.1038/363685a0

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1038/363685a0

This article is cited by

Comments

By submitting a comment you agree to abide by our Terms and Community Guidelines. If you find something abusive or that does not comply with our terms or guidelines please flag it as inappropriate.

Search

Quick links

Nature Briefing

Sign up for the Nature Briefing newsletter — what matters in science, free to your inbox daily.

Get the most important science stories of the day, free in your inbox. Sign up for Nature Briefing