108739-25-9

Basic information

• Product Name: fullerene
• CAS NO: 108739-25-9
• Molecular Weight: 720.66
• Mol File: 108739-25-9.mol
• Article Data: 98

Chemical Properties

• CAS DataBase Reference: fullerene(CAS DataBase Reference)
• NIST Chemistry Reference: fullerene(108739-25-9)
• EPA Substance Registry System: fullerene(108739-25-9)

Safety Data

• Hazardous Substances Data: 108739-25-9(Hazardous Substances Data)

Upstream product

• 943827-64-3 C₇₅H₂₁N₃O₂ 
• 690255-10-8 3'-methyl-1'-(4-nitrophenyl)pyrazolino[60]fullerene 
• 1171848-71-7 1-(1-undecynyl)-1,9-dihydro[60]fullerene 
• 591-50-4 iodobenzene 
• 1207318-60-2 Os3(CO)10(μ,η3-(PPh2)C60H) 
• 177904-73-3 penta(cyclopentadienyl)-η(5)-cyclopentadienylmanganesetricarbonyl 
• 1352145-92-6 Fe(CO)4(C₆₀) 
• 135863-99-9 bis(triphenylphosphine)platinum(η2-C60) 
• 603-32-7 triphenyl-arsane 
• 16774-21-3 ammonium cerium (IV) nitrate 
• 141197-61-7 [76]fullerene 
• 10099-58-8 lanthanum(III) chloride 
• 13463-40-6 iron pentacarbonyl 

Downstream Products

• 150493-27-9 ethyl 3′H-cyclopropa[1,9](C₆₀-I_h)[5,6]fullerene-3′-carboxylate 
• 150493-29-1 tert-butyl 3′H-cyclopropa[1,9](C₆₀-I_h)[5,6]fullerene-3′-carboxylate 
• 154798-96-6 C₇₅H₁₀FNO₃ 
• 158871-73-9 C₇₁H₄F₄N₂O₄ 
• 156551-17-6 1-(dimethylphenylsilylmethyl)-1,9-dihydro(C₆₀-I_h)[5,6]fullerene 

Relevant articles and documents

Phonons and electron-phonon interaction in halogen-fullerene compounds

We have investigated the optical spectra of different halogen-fullerene compounds: C60I4-x, C70I2, C60Br24, C60Cl24, and C70Cl17. Two types of carbon-halogen bonding have been established: (a) C60I4-x and C70I2 compounds are formed by a C60 or C70 molecule sublattice and an I2 molecule sublattice that weakly interact via van der Waals forces; (b) C60Br24, C60Cl24, and C70C117 compounds are characterized by covalent bonds between C and Br/Cl atoms. We have studied in detail the resonance effects in C60Cl24 using the methods of Raman scattering, infrared absorption, and absorption in the visible region. The effect originates from the interactions between the phonon subsystem and the electron band at 2.33 eV and manifests itself in a resonant enhancement of the Raman line intensities and in the repetition of the phonon and the luminescence spectra shifted by the frequency of Raman-active phonon at 1508 cm-1. The group-theory analysis of phonon symmetries in rigid and nonrigid C60Br24 and C60Cl24 crystals has been performed.

Heat capacity measurements and thermodynamic studies of the new compound C60

Heat capacity of the new compound C60 was measured by using a laboratory-made adiabatic calorimeter between liquid helium temperature and room temperature. A phase transition phenomenon was observed as a large heat capacity anomaly extending from 180 to 260 K. The fact that the anomaly has two peaks at 250 and 255 K indicates a complicated mechanism of the phase transition and/or some effects of purity, multi-phases in the sample. The values of enthalpy and entropy of transition were estimated as 6.7 kJmol-1 and 28 JK-1 mol-1, respectively. The normal portion of the heat capacity curve as a whole is very similar to that of graphite. In the lowest temperature region, however, the heat capacity of C60 is much larger than that of graphite. Molecular motion in the crystal of C60 is discussed concerning with the lattice vibrations.

Syntheses and EELS characterization of water-soluble multi-hydroxyl Gd@C 82 fullerenols

Various water-soluble multi-hydroxyl fullerenes (fullerenols), C60(OH)n, C70(OH)n and C84(OH)n, and a Gd metallo-fullerenols, Gd@C82(OH)n have been synthesized by the Kitazawa method. Elementary chemical analyses indicate that all of these fullerenols have 30-40 hydroxyl groups and 11-15 coordinated water molecules via hydrogen bonds. Electron energy loss spectroscopy (EELS) on Gd@C82 fullerenols shows that the π* peak area in the C K-edge spectra decreases on going from intact Gd@C82 metallofullerene to Gd@C82 fullerenols, indicating an increase in sp3 character of the fullerenols. Furthermore, Gd M4,5-edge EELS spectra show that the encapsulated Gd atom has a trivalent Gd3+ state.

The thermodynamic properties of bis(η6-o-xylene)chromium(I) fulleride over the temperature range from T → 0 to 340 K

The temperature dependence of the heat capacity of bis(η6-o- xylene)chromium(I) fulleride, [(η6-(o-xylene)) 2Cr]+?[C60]?-, over the temperature range 6-340 K was measured on an adiabatic va

Penta(cyclopentadienyl)-η 5-cyclopentadienylmanganesetricarbonyl: Structure and laser-induced conversion to fullerenes

The title compound [Cp5CpMn(CO)3], 1, has been characterized by X-ray crystallography and shown by laser-induced desorption/ionization (LDI) to undergo dissociative coalescence to fullerene C60 and other carbon clusters.

Supply of gaseous carbon for the production of fullerenes

The method of fullerene production by graphite evaporation has been modified by adding carbonaceous gases to the noble gas atmosphere. Time of flight mass spectrometry and optical absorption measurements on the reaction products are reported. Whereas simple hydrocarbons prevent the growth of fullerenes the addition of a fluorinated carbonaceous gas yields large carbon molecules in the C2n-sequence, molecules with 2n≠60 at present occurring comparatively abundant.

Endohedral gadolinium-containing metallofullerenes in the trifluoromethylation reaction

An efficient method for the synthesis of trifluoromethyl derivatives of endohedral gadolinium-containing metallofullerenes was proposed. High-purity (98-99%) trifluoromethyl derivatives Gd@C82(CF3) 5 (two isomers) and Gds

High-yield synthesis, separation, and mass-spectrometric characterization of fullerenes C60 to C266

The preparation of fullerenes C60 to C266 in very high yield (up to 44% extractable) by a plasms discharge is reported. Almost one-third of the extractable material is composed of giant fullerenes C84 to C200. An extraction for isolating selected molecular weight fractions of fullerenes is described. The extractions were characterized by time-of-flight mass spectrometry and Fourier transform spectrometry. We find that a Soxhlet extraction with benzene extracts 50% more soluble fullerenes than benzene reflux, Soxhlet extractions with 1,2,3,5-tetramethylbenzene preferentially extract higher molecular weight fullerenes. Hexane to limit the amount of higher fullerenes extracted, giving solutions containing C60 and C70 with only of the higher molecular weight fullerenes. Heptane extraction following the hexane extraction appears to preferentially extract C60, C70, and C80. This solvent scheme is useful in preparing molecular weight fractions for subsequent separation by column chromatography.

Regio- and Stereoselectivity of the [2 + 2] Photocycloaddition of Acyclic Enones to C60

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Kinetic Stability of the C60-Cyclopentadiene Diels-Alder Adduct

Buckminsterfullerene (C60) reacts with cyclopentadiene to produce the Diels-Alder adduct C60C5H6 (1).To determine the thermal stability of adduct 1, we have determined the rates of decomposition in the temperature range 80-90 deg C.Fitting this data to the Arrhenius form of the rate expression give a pre-exponential factor of log A=12.59+/-0.4 and an activation energy of 26.7+/-2.2 kcal/mol.

Functionalization of [60]fullerene and of [60]fullerene monoadducts by photochemical cycloaddition of 4-methyl-1,2,4-triazoline-3,5-dione

The photoreactions of 4-methyl-1,2,4-triazoline-3,5-dione (NMTAD) with C60 and with several fullerene derivatives have been studied. In general, NMTAD cycloadds to C60 and to its monoadducts with closed structures in a highly regioselective [2+2] fashion at a cis-1 [6,6] double bond. Cycloadditions to azafulleroids occur by a slightly different pathway and result in partially cluster-opened bis(adducts). 1,6-Methano[60]fulleroid, however, also undergoes a [2+2+2] cycloaddition in the absence of light. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

Interaction of solid films of C60 and C70 with nickel

Interaction of varying coverages of Ni metal with solid films of C60 and C70 has been investigated by UV and X-ray photoemission spectroscopy. The shifts in the valence bands of C60 (as well as of C70) with increasing Ni coverage accompanied by a shift of the C 1s level of the fullerene to lower binding energies suggest charge-transfer from the metal to the fullerene as in transition metal complexes of π-systems.

On the mechanism of fullerene formation. Trapping of some possible intermediates

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Transition Metal-carbonyl, -hydrido and -η-Cyclopentadienyl Derivatives of the Fullerene C60

Monoadduct derivatives of the fullerene C60, namely 2-C60)>, 2-C60)> (R = H, Bun), 2-C5H5)2(η2-C60)H> and 2-C60)H>, are described.

[2+2] Photocycloadditions of cis/trans-4-propenylanisole to C60. A step-wise mechanism.

The photocycloaddition of cis- and trans-1-(p-methoxyphenyl)-1-propene to C60 gives only the trans [2+2] adducts. Irradiation of the isolated adduct gives a mixture of cis- and trans-1-(p-methoxyphenyl)-1-propene and C60 cycloreversion products. These results exclude a concerted addition and are consonant with a two step mechanism.

Reprint of: Preparation and UV/visible spectra of fullerenes C60 and C70

The preparation and isolation of pure fullerene-60 and fullerene-70 is described. The solution UV/visible absorption spectra of the two molecules are presented.

Thermodynamics of the bis(η6-t-butylphenyl)chromium fulleride [Cr{η6-(t-BuPh)}2]?+C60 ?-

In this work, the temperature dependence of heat capacity C p,mo = f(T) of crystalline bis(η6-t- butylphenyl)chromium fullende between T= 6 and 360K was measured for the first time by precision adiabatic vacuum calorimetry

Construction and photophysics study of supramolecular complexes composed of three-point binding fullerene-trispyridylporphyrin dyads and zinc porphyrin

A series of novel supramolecular complexes composed of a three-point binding C60-trispyridylporphyrin dyad (1) or C70- trispyridylporphyrin dyad (2) and zinc tetraphenylporphyrin (ZnP) were constructed by adopting a covalent-coordinate bonding approach, composed of three-point binding. The dyads and self-assembled supramolecular triads or pentads formed by coordinating the pyridine groups located on the dyads to ZnP, have been characterized by means of spectral and electrochemical techniques. The formation constants of ZnP-1 and ZnP-2 complexes were calculated as 1.4 × 104 M-1 and 2.0 × 104 M-1, respectively, and the Stern-Volmer quenching constants K SV were founded to be 2.9 × 104 M-1 and 5.5 × 104 M-1, respectively, which are much higher than those of other supramolecular complexes such as previously reported ZnP-3 (N-ethyl-2-(4-pyridyl)-3,4-fulleropyrrolidine). The electrochemical investigations of these complexes suggest weak interactions between the constituents in the ground state. The excited states of the complexes were further monitored by time-resolved fluorescence measurements. The results revealed that the presence of the multiple binding point dyads (1 or 2) slightly accelerated the fluorescence decay of ZnP in o-DCB relative to that of the single-point bound supramolecular complex ZnP-3. In comparison with 1 and 2, C70 is suggested as a better electron acceptor relative to C60. DFT calculations on a model of supramolecular complex ZnP-1 (with one ZnP entity) were performed. The results revealed that the lowest unoccupied molecular orbital (LUMO) is mainly located on the fullerene cage, while the highest occupied molecular orbital (HOMO) is mainly located on the ZnP macrocycle ring, predicting the formation of radical ion pair ZnP +-H2P-C60- during photo-induced reaction.

Cage-Expansion of Fullerenes

Despite the first proposal on the cage inflation of fullerenes in 1991, the chemical expansion of fullerenes has been still a formidable challenge. Herein, we provide an efficient methodology to expand [60] and [70]fullerene cages by the inclusion of totally C5N unit, giving nitrogen-containing closed structures as C65N and C75N with double fused heptagons. This method consists of two steps commenced with the construction of an opening by the reaction with triazine as a C3N source, followed by the cage reformation using N-phenylmaleimide as a C2 source. We also synthesized endohedral cages, demonstrating that the encapsulated H2O molecule inside the C75N cage prefers the orientation which maximizes the intramolecular interaction with the carbon wall. Additionally, we revealed the existence of a through-space magnetic dipolar interaction between the encapsulated H2 molecule and the embedded N atom.

Lu2@C2n (2n = 82, 84, 86): Crystallographic Evidence of Direct Lu-Lu Bonding between Two Divalent Lutetium Ions Inside Fullerene Cages

Although most of the M2C2n-type metallofullerenes (EMFs) tend to form carbide cluster EMFs, we report herein that Lu-containing EMFs Lu2C2n (2n = 82, 84, 86) are actually dimetallofullerenes (di-EMFs), namely, Lu2@Cs(6)-C82, Lu2@C3v(8)-C82, Lu2@D2d(23)-C84, and Lu2@C2v(9)-C86. Unambiguous X-ray results demonstrate the formation of a Lu-Lu single bond between two lutetium ions which transfers four electrons in total to the fullerene cages, thus resulting in a formal divalent state for each Lu ion. Population analysis indicates that each Lu atom formally donates a 5d electron and a 6s electron to the cage with the remaining 6s electron shared with the other Lu atom to form a Lu-Lu single bond so that only four electrons are transferred to the fullerene cages with the formal divalent valence for each lutetium ion. Accordingly, we confirmed both experimentally and theoretically that the dominating formation of di-EMFs is thermodynamically very favorable for Lu2C2n isomers.