The chemistry of fullerenes

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.

[1]  R. Haddon,et al.  Thermodynamics of fullerene (C60) in pure oxygen, nitrogen and argon , 1992 .

[2]  Harold W. Kroto,et al.  A postbuckminsterfullerene view of carbon in the galaxy , 1992 .

[3]  G. Olah,et al.  Chlorination and bromination of fullerenes. Nucleophilic methoxylation of polychlorofullerenes and their aluminum trichloride catalyzed Friedel-Crafts reaction with aromatics to polyarylfullerenes , 1991 .

[4]  E. Samulski,et al.  Flagellenes: Nanophase-Separated, Polymer-Substituted Fullerenes , 1992 .

[5]  Y. Saito,et al.  C60Pdn: the first organometallic polymer of buckminsterfullerene , 1992 .

[6]  T. Ebbesen,et al.  Regiochemistry of the bisosmylation of fullerene C60: ortho, meta, and para in three dimensions , 1992 .

[7]  K. Raghavachari.  Structure of C60O: unexpected ground state geometry , 1992 .

[8]  F. Wudl,et al.  The unusual electrochemical properties of the higher fullerene, chiral C76 , 1992 .

[9]  P. Fagan,et al.  The Chemical Nature of Buckminsterfullerene (C60) and the Characterization of a Platinum Derivative , 1991, Science.

[10]  D. Chase,et al.  Multiple, reversible chlorination of C60 , 1991 .

[11]  T. Guarr,et al.  Elevated temperature gel permeation chromatography and electrochemical behaviour of the C84 fullerene , 1993 .

[12]  A. Bard,et al.  Reduction and electrochemistry of fullerene C60 in liquid ammonia , 1992 .

[13]  P. Cahill,et al.  C60H2: Synthesis of the Simplest C60 Hydrocarbon Derivative , 1993, Science.

[14]  D. Chase,et al.  Synthesis and Single-Crystal X-ray Structure of a Highly Symmetrical C60 Derivative, C60Br24 , 1992, Science.

[15]  C. Day,et al.  Solvated C60 and C60/C70 and the low-resolution single crystal X-ray structure of C60 , 1991 .

[16]  A. Balch,et al.  Structure of a Product of Double Addition to C70: [C70{Ir(CO)Cl(PPhMe2)2}2]·3C6H6 , 1992 .

[17]  L. Chiang,et al.  Versatile nitronium chemistry for C60 fullerene functionalization , 1992 .

[18]  R. Hettich,et al.  Characterization and stability of highly fluorinated fullerenes , 1992 .

[19]  G. Olah,et al.  Considered novel aromatic systems. 11. Diamagnetic polyanions of the C60 and C70 fullerenes: preparation, 13C and 7Li NMR spectroscopic observation, and alkylation with methyl iodide to polymethylated fullerenes , 1991 .

[20]  H. Thorp,et al.  Electrochemical reduction of fullerenes in the presence of O2 and H2O: Polyoxygen adducts and fragmentation of the C60 framework , 1991 .

[21]  Henry A. Bent,et al.  An Appraisal of Valence-bond Structures and Hybridization in Compounds of the First-row elements. , 1961 .

[22]  E. G. Hope,et al.  No lubricants from fluorinated C60 , 1992, Nature.

[23]  S. C. O'brien,et al.  C60: Buckminsterfullerene , 1985, Nature.

[24]  R. S. Koefod,et al.  Organometallic chemistry with buckminsterfullerene. Preparation and properties of an indenyliridium(I) complex , 1991 .

[25]  K. Preston,et al.  Electron paramagnetic resonance spectra of R-C60 radicals. Evidence for RC60C60R dimers , 1992 .

[26]  D. Loy,et al.  Synthesis of a C60-p-xylylene copolymer , 1992 .

[27]  V. Catalano,et al.  Supramolecular aggregation of an (.eta.2-C60) iridium complex involving phenyl chelation of the fullerene , 1992 .

[28]  S. Kawata,et al.  The origin of the ESR signal of C60 seen in the powder and in benzene solution. The indication of the reaction of C60 with oxygen induced by photoexcitation , 1992 .

[29]  S. Parkin,et al.  (.eta.2-C70)Ir(CO)Cl(PPh3)2: the synthesis and structure of an iridium organometallic derivative of a higher fullerene , 1991 .

[30]  Isao Ikemoto,et al.  NMR characterization of isomers of C78, C82 and C84 fullerenes , 1992, Nature.

[31]  Michael M. Haley,et al.  Efficient production of C60 (buckminsterfullerene), C60H36, and the solvated buckide ion , 1990 .

[32]  Roger Taylor,et al.  C60, C70, C76, C78 and C84: numbering, π-bond order calculations and addition pattern considerations , 1993 .

[33]  J. Tour,et al.  Purification of gram quantities of C60. A new inexpensive and facile method , 1992 .

[34]  H. Perreault,et al.  C60 and C70 fullerene isomers generated in flames. Detection and verification by liquid chromatography/mass spectrometry analyses. , 1992, Rapid communications in mass spectrometry : RCM.

[35]  Y. Saito,et al.  An X-ray crystallographic analysis of a (BEDT-TTF)2C60 charge-transfer complex , 1992 .

[36]  P. Fowler,et al.  Faraday communications. Hypothetical twisted structure for C60F60 , 1991 .

[37]  G. Roth,et al.  The crystal structure of C70S48: the first ${a~priori}$ structure determination of a C70-containing compound , 1992 .

[38]  K. Preston,et al.  Radical Reactions of C60 , 1991, Science.

[39]  H. Kroto,et al.  Single crystal X-ray structure of benzene-solvated C60 , 1992 .

[40]  Lee W. Tutt,et al.  Optical limiting performance of C60 and C70 solutions , 1992, Nature.

[41]  Douglas J. Klein,et al.  Resonance in C60, buckminsterfullerene , 1986 .

[42]  K. Raghavachari,et al.  Ground state of C70O: oxygen bridging at the equatorial belt , 1992 .

[43]  G. Scuseria,et al.  Exo-fluorinated C60F60 has Ih symmetry , 1992 .

[44]  H. Kroto,et al.  13 C NMR spectroscopy of C76, C78, C84 and mixtures of C86–C102; anomalous chromatographic behaviour of C82, and evidence for C70H12 , 1993 .

[45]  H. Kroto,et al.  Degradation of C60 by light , 1991, Nature.

[46]  F. Wudl,et al.  Systematic Inflation of Buckminsterfillerene C60: Synthesis of Diphenyl Fulleroids C61 to C66 , 1991, Science.

[47]  A. Balch,et al.  Disorder in a crystalline form of buckminsterfullerene: C60·4C6H6 , 1993 .

[48]  E. G. Hope,et al.  Highly oxygenated derivatives of fluorinated C60, and the mode of fragmentation of the fluorinated cage under electron impact lonization conditions , 1993 .

[49]  F. Wudl,et al.  The Higher Fullerenes: Isolation and Characterization of C76, C84, C90, C94, and C70O, an Oxide of D5h-C70 , 1991, Science.

[50]  A. Balch,et al.  A double addition product of C60: C60{Ir(CO)Cl(PMe2Ph)2}2. Individual crystallization of two conformational isomers , 1992 .

[51]  Reginald J. Taylor,et al.  Electrophilic Aromatic Substitution , 1990 .

[52]  A. Hirsch,et al.  Titration of C60: A Method for the Synthesis of Organofullerenes , 1992 .

[53]  V. Catalano,et al.  Accumulating evidence for the selective reactivity of the 6-6 ring fusion of fullerene, C60. Preparation and structure of (.eta.2-C60)Ir(CO)Cl(PPh3)2.cntdot.5C6H6 , 1991 .

[54]  Douglas J. Klein,et al.  Elemental carbon cages , 1988 .

[55]  R. Schlögl,et al.  Material Properties and Purity of C60 , 1992 .

[56]  R. Haddon,et al.  Solid-state magnetic resonance spectroscopy of fullerenes , 1991 .

[57]  D. Bethune,et al.  Carbon-13 NMR study of the C60 cluster in the solid state: molecular motion and carbon chemical shift anisotropy , 1991 .

[58]  R. Cooks,et al.  Reaction of fullerenes and benzyne , 1992 .

[59]  P. Fagan,et al.  Metal complexes of buckminsterfullerene (C60) , 1992 .

[60]  E. G. Hope,et al.  Fluorination of buckminsterfullerene , 1991 .

[61]  R. Cooks,et al.  Oxygen and methylene adducts of C60 and C70 , 1991 .

[62]  F. Wudl,et al.  Globe‐trotting Hydrogens on the Surface of the Fullerene Compound C60H6(N(CH2CH2)2O)6 , 1991 .

[63]  F. Diederich,et al.  Fullerene Sugars: Preparation of Enantiomerically Pure, Spiro‐Linked C‐Glycosides of C60 , 1992 .

[64]  F. Wudl,et al.  Synthesis of m-phenylene- and p-phenylenebis(phenylfulleroids): two-pearl sections of pearl necklace polymers , 1992 .

[65]  H. Kroto,et al.  Preparation and characterization of C60Br6 and C60Br8 , 1992, Nature.

[66]  B. Parkinson,et al.  Electrochemical studies on metal derivatives of buckminsterfullerene (C60) , 1992 .

[67]  J. Johnston,et al.  The absence of ‘globe-trotting’ hydrogen on the surfaces of aminated fullerenes: 3-D hydrogen bonding between aminated fullerenes and water revealed , 1993 .

[68]  I. Amato.  Doing chemistry in the round. , 1991, Science.

[69]  B. Parkinson,et al.  Electron spin resonance study of the radical reactivity of C60 , 1991 .

[70]  Harold W. Kroto,et al.  Isolation, separation and characterisation of the fullerenes C60 and C70 : the third form of carbon , 1990 .

[71]  W. Krätschmer,et al.  Solid C60: a new form of carbon , 1990, Nature.

[72]  P. Kamat,et al.  Visible laser-induced oxidation of C70 on titanium dioxide particles , 1992 .

[73]  G. Westman,et al.  C60 embedded in γ-cyclodextrin: a water-soluble fullerene , 1992 .

[74]  H. Kroto,et al.  Formation of C60Ph12 by electrophilic aromatic substitution , 1992 .

[75]  I. G. Nixon,et al.  CCCXXXII.—Stereochemical influences on aromatic substitution. Substitution derivatives of 5-hydroxyhydrindene , 1930 .

[76]  Y. Ohsawa,et al.  Electrochemical detection of C60 6? at low temperature , 1992 .

[77]  F. Wudl.  The chemical properties of buckminsterfullerene (C60) and the birth and infancy of fulleroids , 1992 .

[78]  Luis Echegoyen,et al.  Electrochemical detection of C606- and C706-: Enhanced stability of fullerides in solution , 1992 .

[79]  F. Wudl,et al.  Dihydrofulleroid HC: Synthesis and properties of the parent fulleroid , 1992 .

[80]  Yoshinori Ando,et al.  Pentagons, heptagons and negative curvature in graphite microtubule growth , 1992, Nature.

[81]  P. Keizer,et al.  The EPR spectra of free radical adducts of C70 , 1992 .

[82]  L. Chiang,et al.  Multi-hydroxy additions onto C60 fullerene molecules , 1992 .

[83]  E. G. Hope,et al.  Nucleophilic substitution of fluorinated C60 , 1992 .

[84]  R. Taylor,et al.  A valence bond approach to explaining fullerene stabilities , 1991 .

[85]  E. Johnston,et al.  Synthesis, chemistry, and properties of a monoalkylated buckminsterfullerene derivative, tert-BuC60 anion , 1992 .

[86]  M. Ohashi,et al.  Addition Reaction of Benzyne to C60 , 1992 .

[87]  J. D. Crane,et al.  Preparation and characterisation of C60(ferrocene)2 , 1992 .

[88]  O. Ermer.  3:1 Molecular Complex of Hydroquinone and C60 , 1991 .

[89]  Robert L. Whetten,et al.  Photophysical properties of C60 , 1991 .

[90]  Y. Rubin,et al.  Synthesis and X-ray structure of a Diels-Alder adduct of C60 , 1993 .

[91]  T. Lewis,et al.  Crystal Structure of Osmylated C60: Confirmation of the Soccer Ball Framework , 1991, Science.

[92]  J. Heath,et al.  Organic chemistry of C60 (Buckminsterfullerene): chromatography and osmylation. , 1991, The Journal of organic chemistry.

[93]  Hsien‐Hau Wang,et al.  Discrete layers of ordered fullerene C60 molecules in the cocrystal C60.cntdot.CH2I2.cntdot.C6H6: synthesis, crystal structure, and carbon-13 NMR properties , 1992 .

[94]  K. Müllen,et al.  Reaction of Buckminsterfullerene with ortho‐Quinodimethane: a New Access to Stable C60 Derivatives , 1993 .

[95]  J. McCauley,et al.  Synthesis and characterization of C60O, the first fullerene epoxide , 1992 .

[96]  R. Whetten,et al.  Reaction of C60 with Dimethyldioxirane—Formation of an Epoxide and a 1,3‐Dioxolane Derivative , 1992 .

[97]  Y. Wang,et al.  Photoconductivity of fullerene-doped polymers , 1992, Nature.

[98]  R. Whetten,et al.  Coalescence reactions of fullerenes , 1992, Nature.

[99]  E. Wasserman,et al.  ESR studies of the reaction of alkyl radicals with fullerene (C60) , 1992 .

[100]  R. Cooks,et al.  Aromatic hydrocarbon derivatives of fullerences , 1991 .