Synthesis and characterization of C60O, the first fullerene epoxide

Creegan, K. M.; Robbins, John L.; Robbins, Win K.; Millar, J. M.; Sherwood, R. D.; Tindall, P.; Cox, D. M.; McCauley, John P.; Jones, David R.

doi:10.1021/ja00029a058

Cited by 477 publications

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“…5 4 indicated the presence of at least two isomers. This suggests either that the soot obtained from MER was formed in a more reducing environment than that from TFC, or that the TFC soot had been exposed to light and air resulting in photo-oxidation (22,23). This difference between the two graphite-derived soots will be referred to below.…”

Section: Resultsmentioning

confidence: 99%

“…3a) postulated to be a necessarily less symmetrical isomer, and correspondingly also contains (Fig. 3b) several chromatographically distinguishable C6,0 isomers including peak A attributable to the fullerene monoxide (22). Similarly, the graphite-derived soot extract contains only the stable C,, fullerene (peak 11, Fig.…”

Section: Resultsmentioning

confidence: 99%

“…2) for m/z 736; this is in accord with expectations (8) based upon a unique monoxide structure for the fully symmetrical C6, fullerene (all carbon atoms equivalent). Recent work (22) has shown that an epoxide structure may be assigned to this unique monoxide of C,, fullerene. As emphasized previously (8), the flame-generated sample contains both the C,, fullerene plus the compound (peak B, Fig.…”

Section: Resultsmentioning

confidence: 99%

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Analysis of minor constituents in fullerene soots by LC–MS using a heated pneumatic nebulizer interface with atmospheric pressure chemical ionization

Anacleto¹,

Boyd²,

Pleasance³

et al. 1992

Can. J. Chem.

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. The minor constituents of toluene extracts of three fullerene-rich materials have been characterized by on-line LC-MS techniques, incorporating both positive and negative ion mass spectra obtained by atmospheric pressure chemical ionization. Two of the materials were soots, produced by resistive heating of graphite in an inert atmosphere, from different commercial suppliers. The third material was obtained as a condensate from a controlled laminar flame, and was shown previously (Anacleto et al:, Rapid Commun. Mass Spectrom. 6 , 214 (1992)) to contain significant quantities of compounds that behaved under the present LC-MS conditions as isomers of the C, and C,, fullerenes, and which reverted to the latter upon heating. This finding was confirmed here, and extended to the higher clusters C,,, C,,, C,,, and C,,. One of the graphite-derived soots contained monoxides of the carbon clusters as the principal minor components, while the other soot contained hydrogenated species including CsoHz, CWHJ, C70H2r and (C6,. CHI). The flame-generated material contained all of these minor constituents, together with complexes of C, with larger aliphatic molecules as well as large quantities of polycyclic aromatic hydrocarbons and related species. Photo-oxidation of a purified C,, preparation, from the graphitic soot containing mostly monoxide impurities, was shown to lead to increased levels of the mono-, di-, and tri-oxides of CGO. Chem. 70, 2558Chem. 70, (1992.Faisant appel i i des techniques de LC-MS incorporant des spectres de masse des ions tant positifs que negatifs obtenus par des ionisations chimiques rCalisCes a la pression atmospherique, on a caractkrise les constituants mineurs obtenus par extraction au toluene de trois materiaux riches en fullerhe. Deux des matCriaux Ctaient des suies fournies par differents fournisseurs commerciaux et obtenue par chauffage de graphite par resistance dans une atmosphkre inerte. Le troisieme materiel a Cte obtenu sous forme de produit de condensation d'une flamrne laminaire contr616e; il a 6tC dCmontr6 antkrieurement (Anacleto et al., Rapid Commun. Mass Spectrom. 6, 214 (1992)) que ce materiel contient des quantites importantes de produits qui se comportent, dans les conditions actuelles de LC-MS, comme des isomeres des fullerknes en C, et en C7, et qui se transfoment en ces derniers par chauffage. On a confirm6 cette conclusion dans le present travail et on l'a Ctendue aux agregats plus importants C76, C84, C90 et C,,. L'une des suies provenant du graphite contient des monoxydes des agrCgats carbonks comme constituants mineurs principaux alors que l'autre contient des especes hydrogCnCes incluant le C6,H2, le C,,H,, le CwH2 et (C,, . CH,). Le materiel gCnCrC par une flamme contient tous ces constituants mineurs en plus de complexes du C,, avec des molCcules aliphatiques plus grosses ainsi que des quantitks irnportantes d'hydrocarbures aromatiques polycycliques et d'especes apparentees. On a montre que la photo-oxydation d'une preparation purifiee de C,, obtenue 2 partir de sui...

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Analysis of minor constituents in fullerene soots by LC–MS using a heated pneumatic nebulizer interface with atmospheric pressure chemical ionization

Anacleto¹,

Boyd²,

Pleasance³

et al. 1992

Can. J. Chem.

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“…They become as large as 1 − 10% or more under the ultraviolet irradiation. The molecular structures of the oxidized C 60 have been reported in the recent experiments [3]. It has been found that an oxygen atom makes two bonds with carbons between which there is a short bond.…”

Section: §1 Introductionmentioning

confidence: 99%

C₆₀with O defects: localized states in the gap and oxygen clustering

Harigaya¹

1992

J. Phys.: Condens. Matter

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We propose a Su-Schrieffer-Heeger type electron-phonon model for C 60 with O defects and solve by the adiabatic approximation. Two new properties are obtained. (1) The dimerization becomes weaker around the oxygen. Two localized states appear deep in the gap. Optical transition between them is allowed. This accords with the recent optical absorption data. (2) Oxygens are predicted to cluster on the surface of C 60 .

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“…The structure can still possess sufficient degree of p-orbital overlap between the cage moieties leading to hyper-conjugation. In such studies, intramolecular fullerene oxide compositions were reported in the reaction of C 60 with molecular oxygen under photoexcitation [18,19] or at elevated temperatures (>370 K) [20], ozone [21,22], and surface adsorbed oxygen atoms at 100-700 K [23]. Apparently, intermolecular fullerene oxide could be made as a dimer of C 60 containing an oxygen bridge.…”

Section: Introductionmentioning

confidence: 99%

Polymeric fullerene oxide films produced by decomposition of hexanitro[60]fullerene

Zhai

Das

Hsu

et al. 2004

Carbon

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Synthesis and characterization of C60O, the first fullerene epoxide

Cited by 477 publications

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Analysis of minor constituents in fullerene soots by LC–MS using a heated pneumatic nebulizer interface with atmospheric pressure chemical ionization

Analysis of minor constituents in fullerene soots by LC–MS using a heated pneumatic nebulizer interface with atmospheric pressure chemical ionization

C₆₀with O defects: localized states in the gap and oxygen clustering

Polymeric fullerene oxide films produced by decomposition of hexanitro[60]fullerene

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Synthesis and characterization of C60O, the first fullerene epoxide

Cited by 477 publications

References 0 publications

Analysis of minor constituents in fullerene soots by LC–MS using a heated pneumatic nebulizer interface with atmospheric pressure chemical ionization

Analysis of minor constituents in fullerene soots by LC–MS using a heated pneumatic nebulizer interface with atmospheric pressure chemical ionization

C60with O defects: localized states in the gap and oxygen clustering

Polymeric fullerene oxide films produced by decomposition of hexanitro[60]fullerene

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C₆₀with O defects: localized states in the gap and oxygen clustering