Chapter 9. Fullerene Reactivity – Fullerene Cations and Open-Cage Fullerenes

  1. Prof. Michael M. Haley2 and
  2. Prof. Rik R. Tykwinski3
  1. Toshikazu Kitagawa,
  2. Yasujiro Murata and
  3. Koichi Komatsu

Published Online: 13 JUN 2006

DOI: 10.1002/3527607994.ch9

Carbon-Rich Compounds: From Molecules to Materials

Carbon-Rich Compounds: From Molecules to Materials

How to Cite

Kitagawa, T., Murata, Y. and Komatsu, K. (2006) Fullerene Reactivity – Fullerene Cations and Open-Cage Fullerenes, in Carbon-Rich Compounds: From Molecules to Materials (eds M. M. Haley and R. R. Tykwinski), Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, FRG. doi: 10.1002/3527607994.ch9

Editor Information

  1. 2

    Department of Chemistry, University of Oregon, Eugene, Oregon 97403-1253, USA

  2. 3

    Department of Chemistry, University of Alberta, Edmonton, Alberta, T6G 2G2, Canada

Author Information

  1. Institute for Chemical Research (ICR), Kyoto University, Gokasho, Uji, Kyoto 611-0011, Japan

Publication History

  1. Published Online: 13 JUN 2006
  2. Published Print: 6 FEB 2006

ISBN Information

Print ISBN: 9783527312245

Online ISBN: 9783527607990

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Keywords:

  • carbon-rich compounds;
  • fullerene reactivity;
  • fullerene cations;
  • open-cage fullerenes;
  • functionalized fullerene cations;
  • derivatized C60 and C70 cations;
  • electrophilic functionalization of carbon nanotubes

Summary

This chapter contains sections titled:

  • Introduction

  • Functionalized Fullerene Cations

    • Derivatized C60 and C70 Cations

      • Generation of Derivatized C60 and C70 Cations as Long-lived Species

      • Reactions via RC60+ and RC70+ Intermediates

      • Thermodynamic Stabilities of RC60+ and RC70+

    • Aza[60]fullerene Cation C59N+

      • Generation of C59N+

      • Reactions via C59N+

    • Electrophilic Functionalization of Carbon Nanotubes

  • Open-Cage Fullerenes to Endohedral Fullerenes

    • Synthesis of Open-Cage Fullerene Derivatives

      • An Open-Cage Fullerene with a 14-Membered-Ring Orifice

      • Open-Cage Fullerenes with a 12-Membered-Ring Orifice

      • Enlargement of the Orifice by Insertion of a Sulfur Atom

      • Enlargement of the Orifice by Reaction with Aromatic Hydrazine or Diamine

    • Insertion of a Small Guest into Open-Cage Fullerene Derivatives

      • Insertion of a Helium Atom and a Hydrogen Molecule

      • Insertion of a Water Molecule

    • Synthesis of an Endohedral Fullerene by Closure of the Orifice

  • Summary and Conclusion

  • Experimental: Selected Procedures

    • Synthesis of 1-Chloro-4-dichloromethyl-1,4-dihydro[60]fullerene (12b)

    • Synthesis of 1-Dichloromethyl-4-hydroxy-1,4-dihydro[60]fullerene (2b)

    • Generation of Dichloromethylated [60]Fullerene Cation (3b)

    • Synthesis of an Open-Cage Fullerene with an Eight-membered-ring Orifice (49)

    • Synthesis of an Open-Cage Fullerene with a 12-Membered-ring Orifice (54)

    • Synthesis of an Open-Cage Fullerene with a 13-Membered-ring Orifice (56)