Globe-trotting Hydrogens on the Surface of the Fullerene Compound C60H6(N(CH2CH2)2O)6

Authors

  • Dr. Andreas Hirsch,

    1. Institute for Polymers and Organic Solids Department of Physics and Chemistry, University of California Santa Barbara, California 93106 (USA)
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  • Dr. Qiaoying Li,

    1. Institute for Polymers and Organic Solids Department of Physics and Chemistry, University of California Santa Barbara, California 93106 (USA)
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  • Prof. Dr. Fred Wudl

    Corresponding author
    1. Institute for Polymers and Organic Solids Department of Physics and Chemistry, University of California Santa Barbara, California 93106 (USA)
    • Institute for Polymers and Organic Solids Department of Physics and Chemistry, University of California Santa Barbara, California 93106 (USA)
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  • This work was supported by the Deutsche Forschungsgemeinschaft (post-doctoral fellowship for A. H.) as well as NSF Grants DMR-88-20933 and CHE89-08323 to F. W.

  • Dedicated to Professor Michael Hanack on the occasion of his 60th birthday

Abstract

The [1,5] sigmatropic migration of hydrogen in the adduct between buckminsterfullerene C60 and morpholine (Hmorph) is fast at −25°C already. Elemental analysis, thermogravimetry, IR and NMR spectroscopy, and cyclic voltammetry all support the formulation of the adduct as C60H6 (morph)6. The amine is covalently added to six pyracylene units. The small activation barrier to the migration is astounding, especially as large changes in the C60 framework are involved.

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