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Part of the book series: NATO ASI Series ((NSSE,volume 297))

Abstract

The fullerene family of highly symmetrical carbon molecules (C60, C70, etc.) offers considerable potential for the construction of new solids with novel properties some of which can be predicted, others of which can only be discovered. Since the revelation that these molecules, which were originally only available as exotic gas phase entities [1], can be made and chemically purified in macroscopic amounts [2,3]; there has been a flurry of interest in developing their chemistry. A number of significant aspects of the chemistry of the fullerenes have emerged and are of particular relevance to the chemistry developed in this chapter [4–6]. The shorter bonds at 6:6 ring junctions have olefinic reactivity. Multiple additions to these sites occur readily and frequently reversibly. Because of the high symmetry of these molecules, the distinction between reactive sites is low. Frequently, when multiple additions occur, it is difficult to control the level (or stoichiometry) of addition and the regiochemistry of the addition. Separation of pure derivatives of the fullerenes frequently requires extensive chromatography. Crystallization of the fullerenes and their simple derivatives produces solids in which the fullerenes exhibit orientational disorder. This greatly complicates studies of fullerenes and their derivatives by single crystal X-ray crystallography, a technique which is usually definitive for the characterization of simple organometallic compounds. The fullerenes readily undergo electron transfer reactions. For example, C60 undergoes six reversible reductions [7]. Certain fullerene salts, for example K3C60, exhibit superconductivity with remarkably high Tc values [8].

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References

  1. Kroto, H. W.,Heath, J. R., O’Brien, S. C., Curl, R. F., and Smalley, R.E. (1985) C60:BuckminsterFullerene,Nature 318 162–163.

    Article  CAS  Google Scholar 

  2. Krätschmer,W.,Lamb, L. D., Fostiropoulos, K., and Huffman, D. R. (1990) Solid C60 - A New Form ofCarbon,Nature 347 354–358.

    Article  Google Scholar 

  3. Taylor, R.,Hare, J. P., Abdul-Sada, A. K., and Kroto, H. W. (1990) Isolation, Separationand Characterization of the Fullerenes C60 and C70 - TheThird Form of Carbon,J. Chem. Soc. Chem. Commun 1423–1424.

    Google Scholar 

  4. Taylor, R.(1993) The Chemistry of Fullerenes,Nature 363 685–693.

    Article  CAS  Google Scholar 

  5. Fagan, P. J.,Chase, B., Calabrese, J. C., Dixon, D. A., Harlow, R., Krusic, P. J.,Matsuzawa, N., Tebbe, F. N., Thorn, D. L., and Wasserman, E. (1992) Some Wellcharacterized Chemical Reactivities of Buckminster Fullerene (C60),Carbon 30 1213–1226.

    Article  CAS  Google Scholar 

  6. Balch, A. L.(1995) Reactions of Fullerenes with Inorganic and Organometallic Compounds, inThe Chemistry of Fullerenes, Taylor, R. ed. World Scientific Publishing Co.PTE. LTD.

    Google Scholar 

  7. Zie, Q.,Perez-Cordero, E,, and Echegoyen, L. (1992) Electrochemical Detection ofC öo6 andC70 6-:Enhanced Stability of Füllendes in Solution, J. Am. Chem. Soc 114 3978–3980.

    Article  Google Scholar 

  8. Haddon, R. C.(1992) Electronic Structure, Conductivity and Superconductivity of Alkali MetalDoped C60,Accounts Chem. Res 25127–133.

    Article  CAS  Google Scholar 

  9. Vaska, L. (1968)Reversible Activation of Covalent Molecules by Transition Metal Complexes. TheRole of the Covalent Molecule,Accounts Chem. Res 1, 335–344.

    Article  CAS  Google Scholar 

  10. Balch, A. L.,Catalano, V. J., and Lee, J. W. (1991) Accumulating Evidence for the SelectiveReactivity of the6-6 Ring Fusion of Cöo-Preparation andStructure of (n2-C60)Ir(CO)Cl(PPh3)2*5C6H6,Inorg. Chem 30 3980–3981.

    Article  CAS  Google Scholar 

  11. Balch, A. L.,Catalano, V. J., Lee, J. W., Olmstead, M. M., and Parkin, S. R. (1991) (n2-C70)Ir(CO)Cl(PPh3)2 The Synthesisand Structure of An Organometallic Derivative of a Higher Fullerene,J. Am.Chem. Soc 1138953–8954.

    Article  CAS  Google Scholar 

  12. Balch, A. L.,Ginwalla, A. S., Lee, J. W., Noll, B. C., and Olmstead, M. M. (1994) PartialSeparation and Structural Characterization of C84 Isomers by Crystallization of(n2-C84)Ir(CO)Cl(PPh3)2,J. Am. Chem. Soc 116, 2227– 2228

    Article  CAS  Google Scholar 

  13. Balch, A. L.,Costa, D. A., Lee, J. W., Noll, B. C., and Olmstead, M. M. (1994) DirectingEffects in a Fullerene Epoxide Addition. Formation and StructuralCharacterization of (n2-C60O)Ir(CO)Cl(PPh3)2 Inorg. Chem 33, 2071–2072.

    Article  CAS  Google Scholar 

  14. Balch, A. L.,Lee, J. W., and Olmstead, M. M. (1992) Isolation and StructuralCharacterization of a Product of Double Addition toC70: C70PIr(CO)Cl(PPhMe2)2 2*2C6H6,Angew. Chem. Internal Ed. Engl 311356–1358.

    Article  Google Scholar 

  15. Balch, A. L.,Lee, J. W., Noll, B. C., and Olmstead, M. M. (1992) A Double Addition Productof C60: C60(Ir(CO)Cl(PMe2Ph)2 2. Individual Crystallization of TwoConformational Isomers,J. Am. Chem. Soc 11410984–10985.

    Article  CAS  Google Scholar 

  16. Balch, A. L.,Lee, J. W., Noll, B. C., and Olmstead, M. M. (1994) Multiple Additions ofVaska-Type Iridium Complexes toCöo« PreferentialCrystallization of the “Para” Double Addition Products C60Ir(CO)Cl(PMe3)22*2C6H6andC60lr(CO)Cl(PEt3)22*C6H6iInorg. Chem in press.

    Google Scholar 

  17. Meidine,M. F., Hitchcock, P.B., Kroto, H. W., Taylor, R., and D. R. M. Walton. (1992) Single Crystal X-rayStructure of Benzene Solvated C60 J. Chem. Soc.Chem. Commun 1534–1536.

    Google Scholar 

  18. Balch, A. L.,Lee, J. W., Noll, B. C., and Olmstead, M. M. (1993) Disorder in a CrystallineForm of Buckminsterfullerene: C60*4C6H6,J. Chem. Soc. Chem. Commun56–58.

    Google Scholar 

  19. Burgi, H. B.,Restori, R., Schwarzenbach,D.,Balch, A. L., Lee, J. W., Noll, B. C., and Olmstead, M. M. (1994)Nanocrystalline Domains of a Monoclinic Modification of Benzene Stabilized in aCrystalline Matrix of C60 Chem. Matt in press.

    Google Scholar 

  20. Balch, A. L.,Catalano, V. J., Lee, J. W., and Olmstead, M. M. (1992) SupramolecularAggregation of (n2-C60) Iridium Complex Involving Phenyl Chelation of theFullerene,J. Am. Chem. Soc 114 5455–5457.

    Article  CAS  Google Scholar 

  21. Roth, G., Adelmann,P.,and Knitter, R. (1993) Preparation and Crystal Structure ofC60(S8)CS2A New Fullerene Containing Heteromolecular Solid,Materials Letters 16 357–363.

    Article  CAS  Google Scholar 

  22. Burgi, H. B.,Venugopalan, P., Schwartzenbach, D., Diederich, F., and Thilgen, C.(1993) The Crystal Structure of C706(S8) at 100K,Helv. Chim. Acta 76 2155–2159.

    Article  Google Scholar 

  23. Michel, R. H., Kappes, M. M., Adelman,P. and Roth G. (1994) Preparation and Crystal Structure of C76(S8)6,Angew.Chem. Int. Ed. Engl in press.

    Google Scholar 

  24. Douthwaite, R.E., Green, M. L. H., Heyes, S. J., Rosseinsky, M. J., and Turner, J.F.C.(1994) Synthesis and Characterization of the Inclusion Complex (P4)2C60),Chem.Soc. Chem. Commun 1367–1368.

    Google Scholar 

  25. Locke, I. W.,Darwish, A. D., Kroto, H. W., Prassides, K., Taylor, R.,Walton, D. R. M. (1994) Phosphorus/Buckminster Fullerene IntercalationCompound, C60P4 2 Chem. Phys. Lett 225 186–190.

    Article  CAS  Google Scholar 

  26. Crane, J. D.,Hitchcock, P. B., Kroto, H. W., Taylor, R., and Walton, D. R. M. (1992)Preparation and Characterization ofC60(Ferrocene)2,Chem.Soc. Chem. Commun 1764–1765.

    Google Scholar 

  27. Stirchcombe, J.,Penicaud, A., Bhyrappa, P., Boyd, P. D. W., and Reed, C. A. (1993)Buckminsterfulleride(l-) Salts: Synthesis, EPR and the Jahn-Teller DistortionofC60 J-Am. Chem.Soc 1155212–5217.

    Article  Google Scholar 

  28. Balch, A. L.,Lee, J. W., Noll, B. C., and Olmstead, M. M. (1994) A Crystalline Salt of(C60 -) [n5-C5H5)2Co+](C60 -)*CS2,RecentAdvances in the Chemistry and Physics of Fullerenes Kadish, K. M. andRouff, R. eds. Electrochemical Society, Pennington, NJ, in press.

    Google Scholar 

  29. Bossard,C., Rigant, S., Astruc, D., Delville, M.-H., Felix, G., Feurier-Bonvier, A., Amiell, J., Flandrois,S., and Delhaes, P. (1993)One-,Two-and Three-electronReduction of C60 using the Electron-reservoir Complex [FeI(C5H5)(C6Me6)],J. Chem. Soc. Chem. Commun 333–334.

    Google Scholar 

  30. Crane, J. D. andHitchcock, P. B. (1993) Crystallographic Characterization of the LatticeStructure C60*[Fe4(CO)4(n5-C5H5)4] as the 3 BenzeneSolvate, J. Chem. Soc. Dalton Trans 2537–2538.

    Google Scholar 

  31. Fisher, J. E.(1994) Fullerene Polymers from Solid Precursors?,Science 2641548–1549.

    Article  Google Scholar 

  32. Loy, D. A. andAssink, R. A. (1992) Synthesis of a C60 -p-Xylylene Copolymer,J. Am. Chem.Soc 114 3977–3978.

    Article  CAS  Google Scholar 

  33. Rao, A. M.,Zhou, P., Wang, K. A., Hager, G. T., Holden, J. M., Wang, Y.,Lee, W.-T., Bi, X.-X., Eklund, P. C., Cornett, D. S., Duncan, M. A., andAmster, I. J. (1993) Photoinduced Polymerization of SolidCöo Films, Science 259 955–957.

    CAS  Google Scholar 

  34. Martin, M. C., Koller, D., Du, X., Stevens, P.W., and Mihaly, L. (1994) Insulating and Conducting Phases of RbC60 Phys.Rev. B-Condensed Matter 49, 10818–10821.

    Article  CAS  Google Scholar 

  35. Iwasa, Y.,Arima, T., Fleming, R. M., Siegrist, T., Zhou, O., Haddon, R. C., Rothberg,L.S., Lyons, K. B., Carter, Jr., H. L., Hebard, A. F., Tycko, R,Dabbagh, G., Krajewski, J. J., Thomas G. A., and Yagi, T. (1994) New Phases ofC60 Synthesized at High Pressure,Science 264 1570–1572.

    Article  CAS  Google Scholar 

  36. Balch, A. L.,Ginwalla, A. W., and Olmstead, M. M. Unpublished results.

    Google Scholar 

  37. Nagashima, H.,Nakaoka, A., Saito, Y., Kato, M., Kawanishi, T., and Itoh, K. (1992) CöoPdnThe1stOrganometallic Polymer of Buckminsterfullerene, J. Chem. Soc.yChem. Commun 377–379.

    Google Scholar 

  38. Nagashima, H.,Nakaoka, A., Tajima, S., Saito, Y., and Itoh, K. (1992) Catalytic Hydrogenationof Olefins and Acetylenes Over C60 Pdn,Chem. Lett1361–1364.

    Google Scholar 

  39. Balch, A. L.(1993) Construction of Small Polynuclear Complexes with TrifunctionalPhosphine-Based Ligands as Backbones,Prog. Inorg. Chem 41239–330.

    Article  Google Scholar 

  40. Wang, H.-H.,Pignolet, L. H., Reedy, Jr., P. E., Olmstead, M. M., and Balch, A. L.Inorg.Chem 26, 377–383.

    Google Scholar 

  41. Balch, A. L.,Davis, B. J., and Olmstead, M. M. (1990) Metal Ions as Ligands: Complexation ofTin(II)Chloride by the Bidentate Ligand Ir2(CO)2Cl2Ph2P(CH2)4PPh2 2 Jnorg. Chem 29, 3066–3068.

    Article  CAS  Google Scholar 

  42. Balch, A. L.,Davis, B. J., Lee, J. W., Noll, B. C., and Olmstead, M. M. Unpublished results.

    Google Scholar 

  43. Fedurco, M.,Costa, D., Balch, A. L., and Fawcett, W. R. (1994) Electrochemical Synthesis ofa Conducting Polymer Based on Buckminster Fullerene Epoxide,Angew. Chem.Int. Ed. Engl in press.

    Google Scholar 

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Balch, A.L. (1995). Construction of Ordered Solids and Polymers from Fullerene Components. In: Harrod, J.F., Laine, R.M. (eds) Applications of Organometallic Chemistry in the Preparation and Processing of Advanced Materials. NATO ASI Series, vol 297. Springer, Dordrecht. https://doi.org/10.1007/978-94-011-0337-4_16

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  • DOI: https://doi.org/10.1007/978-94-011-0337-4_16

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