Isolation of the Heterofullerene C
 59
 N as Its Dimer (C
 59
 N)
 2

Hummelen, Jan C.; Knight, Brian; Pavlovich, J.; González, R.; Wudl, Fred

doi:10.1126/science.269.5230.1554

Cited by 605 publications

(474 citation statements)

References 13 publications

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“…The undoped part of the single crystals was subsequently dissolved in toluene to give free-standing films of Rb 1 C 60 . The preparation of (C 59 N) 2 has been described previously [15]. After purification by multi"-cycle high-performance liquid chromatography, solid (C 59 N) 2 grains were obtained by evaporation of o-dichlorobenzene followed by recrystallization from a CS 2 solution.…”

Section: Methodsmentioning

confidence: 99%

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The electronic structure of polymerized fullerenes and dimerized heterofullerenes

Pichler

Knupfer²,

Golden³

et al. 1997

Applied Physics A: Materials Science & Processing

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The electronic structure of polymerized fullerenes and dimerized heterofullerenes Pichler, T.; Knupfer, M.; Golden, M.S.; Fink, J.; Winter, J; Haluska, M.; Kuzmany, H.; Keshavarz, K.; Bellavia-Lund, C.; Sastre, A. Take-down policy If you believe that this document breaches copyright please contact us providing details, and we will remove access to the work immediately and investigate your claim.Downloaded from the University of Groningen/UMCG research database (Pure): http://www.rug.nl/research/portal. For technical reasons the number of authors shown on this cover page is limited to 10 maximum. Abstract. We present studies of the electronic structure of polymerized orthorhombic Rb 1 C 60 and dimerised C 59 N using electron energy-loss spectroscopy in transmission. From the C1s excitation spectra a reduced density of π* states is observed for polymerized Rb 1 C 60 . This is in contrast to (C 59 N) 2 and can be explained by the different type of 'doping' and by the different bonding between the fullerene molecules in the two systems. Additional information about the optical properties was obtained from the low energy loss function. Using a Kramers-Kronig analysis, the dielectric function, (ε), and the optical conductivity, (σ), have been derived. ε(0) and the onset of the spectral weight have been compared between the polymer, the dimer and C 60 . This onset of spectral weight is found to be at 1.2 and 1.4 eV for o-Rb 1 C 60 and for (C 59 N) 2 , respectively.

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Section: Methodsmentioning

confidence: 99%

“…The synthesis and isolation of bulk quantities of the first so-called heterofullerene, (C 59 N) 2 [15], have recently allowed the first analysis of the physical and chemical properties of these dimers in the solid state. The crystal structure of pristine (C 59 N) 2 has been studied [16,17] by x-ray diffraction on sublimed material (i.e.…”

mentioning

confidence: 99%

The electronic structure of polymerized fullerenes and dimerized heterofullerenes

Pichler

Knupfer²,

Golden³

et al. 1997

Applied Physics A: Materials Science & Processing

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“…1,2 In general, carbon allotropes like fullerenes, carbon nanotubes and graphene represent an emerging research field. [3][4][5] Particularly, graphene based materials have gained enormous attention due to their fascinating electronic properties.…”

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confidence: 99%

Selective oxidative conversion of triaryldihydro[C59N]fullerenes: a model case for oxygenation of carbon allotropes

2014

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The photooxidation of triaryldihydro [C 59 N]fullerenes was achieved by treatment with air and light leading to a new selective core functionalization of azafullerenes, which serves as a model case for oxygenation of carbon allotropes.To date, azafullerenes, in which one carbon atom of the C 60 skeleton is substituted by nitrogen, are the only class of heterofullerenes that are accessible in macroscopic quantities. 1,2 In general, carbon allotropes like fullerenes, carbon nanotubes and graphene represent an emerging research field. 3-5 Particularly, graphene based materials have gained enormous attention due to their fascinating electronic properties. 6 In this regard, graphene oxide 7 plays an important role as a promising precursor for wet chemical synthesis of graphene with minimal defects. 8 Its structure contains epoxy and hydroxyl groups in addition to carboxylic acids at the edges of the graphene oxide layers according to the Lerf-Klinowski model. 9,10 However, the oxygenation mechanism behind structures like graphene oxide is still not understood. Even the structure elucidation is still in progress. 11 In addition, the chemical doping of graphene with nitrogen leads to promising materials that have already shown superior preferences towards various applications. 12 However, chemical reactions on N-doped graphenes are an unaddressed issue. In this context, fullerenes, in general, provide a very suitable model system to study oxygenation reactions and the stability of products due to their monodispersity and the possibility of using unambiguous characterization methods such as mass spectrometry, NMR spectroscopy and X-ray single crystal analysis. Here, we report on selective oxygenation reactions of azafullerene derivatives providing valuable insights into carbon allotrope oxides and their formation mechanism.The azafullerene dimer can be obtained by a three-step reaction starting from C 60 . 1,2 Covalent functionalization of C 59 N monoadducts such as C 59 NAr has been investigated quite extensively; 13,14 however, heterofullerene derivatives with a higher degree of addition have only been generated in a few cases, 15-21 in contrast to the corresponding rich chemistry of the isocyclic fullerene C 60 . However, the establishment of a C s -symmetrical 6,8,12,15,18-addition motif, also known for C 60 fullerene derivatives, 22,23 was first demonstrated by our group with the successful synthesis of tetrachlorinated aryladduct C 59 NArCl 4 bearing an integral pyrrole moiety within the p-system of the fullerene surface. 16 Recently, we explored the formation of pentaarylazafullerene C 59 NAr 5 by an acid catalyzed reaction of a C 59 N precursor with electron-rich aromatic compounds. During the course of these reactions, triaryldihydroazafullerenes C 59 NAr 3 H 2 1-4 were formed as stable intermediates. 20,21 Furthermore, they exhibit the same pentakisaddition pattern, but contain an unusual pyrrole substructure with allylic hydrogen atoms. The reactivity of these triaryldihydroazafullerenes is still unexplored,...

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“…Also, valuable structural information may be obtained concerning nanoparticle composition through knowledge of fragmentation pathways and the relative abundances of nanoparticle components. Beyond its widely acknowledged applications in biological, molecular, and polymeric systems, MS has been successfully used to characterize various nanoparticles such as fullerenes [17,18], silica clusters [19], metal chalcogenide clusters [20 -24], gold nanocrystals [25][26][27][28], and several other nanomaterials [29 -33].…”

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confidence: 99%

Characterization of synthesized titanium oxide nanoclusters by MALDI-TOF mass spectrometry

Guan

Lü

Fang

et al. 2007

J. Am. Soc. Mass Spectrom.

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Titania represents an important material that has wide applications. The bactericidal efficiency of TiO 2 has been shown to be dependent on the size of the nanoparticles, so it is important to be able to reliably estimate their dimensions. In this study, a stable TiO 2 cluster suspension is produced by the thermal solvent process, and ultrasmall clusters (Ͻ1 nm) with different sizes are obtained by size-selection treatment. MALDI-TOF-MS and LDI-TOF-MS are shown to be useful for characterization of these ultrasmall nanoparticles. Peak maxima are found to correlate with nanoparticle size, and the possibility of using these mass spectrometry-based approaches to estimate nanoparticle size is affirmed. The size distributions of TiO 2 nanoparticles obtained from MALDI-and LDI-TOF-MS are in good agreement with parallel TEM observations. Finally, PSD analysis of inorganic nanomaterials is performed and valuable information about the structure of analytes has been obtained. (J Am Soc Mass Spectrom 2007, 18, 517-524)

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Isolation of the Heterofullerene C ₅₉ N as Its Dimer (C ₅₉ N) ₂

Cited by 605 publications

References 13 publications

The electronic structure of polymerized fullerenes and dimerized heterofullerenes

The electronic structure of polymerized fullerenes and dimerized heterofullerenes

Selective oxidative conversion of triaryldihydro[C59N]fullerenes: a model case for oxygenation of carbon allotropes

Characterization of synthesized titanium oxide nanoclusters by MALDI-TOF mass spectrometry

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Isolation of the Heterofullerene C 59 N as Its Dimer (C 59 N) 2

Cited by 605 publications

References 13 publications

The electronic structure of polymerized fullerenes and dimerized heterofullerenes

The electronic structure of polymerized fullerenes and dimerized heterofullerenes

Selective oxidative conversion of triaryldihydro[C59N]fullerenes: a model case for oxygenation of carbon allotropes

Characterization of synthesized titanium oxide nanoclusters by MALDI-TOF mass spectrometry

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Isolation of the Heterofullerene C ₅₉ N as Its Dimer (C ₅₉ N) ₂