A step toward direct fullerene synthesis: C60 fullerene precursors with fluorine in key positions

Kabdulov, Mikhail; Amsharov, Konstantin; Jansen, Martin

doi:10.1016/j.tet.2010.09.055

Cited by 20 publications

(25 citation statements)

References 25 publications

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“…[16] The samples were purified by temperature gradient sublimation in vacuo. MS experiments were conducted on an AXIMA-QIT-TOF MS (quadrupole ion trap time of flight mass spectrometer), Shimadzu Biotech, 337 nm nitrogen laser.…”

Section: Methodsmentioning

confidence: 99%

Bottom‐Up C₆₀ Fullerene Construction from a Fluorinated C₆₀H₂₁F₉ Precursor by Laser‐Induced Tandem Cyclization

Kabdulov

Jansen

Amsharov

2013

Chemistry A European J

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Wrap up: A specially fluorinated C60 fullerene precursor (see figure) was converted to the target C60 cage by laser ionization, resulting in highly selective HF elimination without any detectable side reactions or undesired fragmentation. The fully selective transformation to the target fullerene has been unambiguously demonstrated from a 13C‐labeled precursor. In general the findings open new horizons for the synthesis of carbon‐based nanomaterials, which cannot be obtained by any conventional alternative method.

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Section: Methodsmentioning

confidence: 99%

Bottom‐Up C₆₀ Fullerene Construction from a Fluorinated C₆₀H₂₁F₉ Precursor by Laser‐Induced Tandem Cyclization

Kabdulov

Jansen

Amsharov

2013

Chemistry A European J

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“…[45] 1-Bromo-2-ethylnaphthalene (16) was synthesized by bromination of 2-ethylnaphthalene with N-bromosuccinimide in acetonitrile. Condensation in odichlorobenzene with TiCl 4 in a closed ampoule at 160°C [48,49] resulted in a complex mixture, which was not further analyzed. 1-(1-Bromonaphthalen-2-yl)ethanone (17) was obtained in one step by oxidation using KMnO 4 in acetone/H 2 O.…”

Section: Precursor For the End-cap Of A (9 9) Armchair Swcntmentioning

confidence: 99%

Synthesis of Precursors for Large‐Diameter Hemispherical Buckybowls and Precursors for Short Carbon Nanotubes

Mueller

Amsharov

2012

Eur J Org Chem

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“…9,10 In this contribution, we instead explore how X-PAH···X-PAH interactions modify this fragmentation scenario. For this we have studied the thermal decomposition of solid X-PAH films of various thicknesses ranging from submonolayer to multilayer.…”

Section: Introductionmentioning

confidence: 99%

Thermal Decomposition of the Fullerene Precursor C₆₀H₂₁F₉ Deposited on Graphite

et al. 2015

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Specially fluorinated polycyclic aromatic hydrocarbons (F-PAHs) are of interest as precursors for transition metal catalyzed CVD growth of chiral-index pure singlewalled carbon nanotubes as well as for the rational synthesis of fullerenes. Laser desorption/ ionization of a prototypical F-PAH has recently been shown to lead to C 60 via a sequence of regioselective intramolecular cyclodehydrofluorination steps: C 60 H on graphite under UHV conditions toward exploring the extent to which such intramolecular dehydrofluorination can also occur on a hot chemically inert surface and to what extent intermolecular interactions influence such transformation processes. C 60 H 21 F 9 films were probed in situ by ultraviolet photoionization, X-ray ionization, Raman spectroscopy, and thermal desorption mass spectrometry, as well as by ex situ atomic force microscopy. Heating multilayer films results first in C 60 H 21 F 9 emission from the bulk (peaked at ∼630 K) followed at higher temperatures by desorption from the interface region (in the range 750−850 K). Sublimation from the interface region is also associated with some on-surface cyclo-dehydrofluorination as indicated by C 60 H 21−n F 9−n , n = 1, 2, 3 emission. C 60 was not observed in the desorbed material suggesting that complete cage closure cannot be achieved on HOPG. Furthermore, C 60 H 21 F 9 deposits cannot be fully removed from HOPG. Instead, competing on-surface polycondensation of reactive intermediates yields a fluorinated carbon phase, which remains stable up to at least ∼1000 K. To complement these studies we have also used mass selective ion beam soft-landing to probe the desorption properties of monodispersed films consisting of mass-selected C 60 H 21−n F 9−n fragments, n = 1, 2.

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A step toward direct fullerene synthesis: C60 fullerene precursors with fluorine in key positions

Cited by 20 publications

References 25 publications

Bottom‐Up C₆₀ Fullerene Construction from a Fluorinated C₆₀H₂₁F₉ Precursor by Laser‐Induced Tandem Cyclization

Bottom‐Up C₆₀ Fullerene Construction from a Fluorinated C₆₀H₂₁F₉ Precursor by Laser‐Induced Tandem Cyclization

Synthesis of Precursors for Large‐Diameter Hemispherical Buckybowls and Precursors for Short Carbon Nanotubes

Thermal Decomposition of the Fullerene Precursor C₆₀H₂₁F₉ Deposited on Graphite

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A step toward direct fullerene synthesis: C60 fullerene precursors with fluorine in key positions

Cited by 20 publications

References 25 publications

Bottom‐Up C60 Fullerene Construction from a Fluorinated C60H21F9 Precursor by Laser‐Induced Tandem Cyclization

Bottom‐Up C60 Fullerene Construction from a Fluorinated C60H21F9 Precursor by Laser‐Induced Tandem Cyclization

Synthesis of Precursors for Large‐Diameter Hemispherical Buckybowls and Precursors for Short Carbon Nanotubes

Thermal Decomposition of the Fullerene Precursor C60H21F9 Deposited on Graphite

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Bottom‐Up C₆₀ Fullerene Construction from a Fluorinated C₆₀H₂₁F₉ Precursor by Laser‐Induced Tandem Cyclization

Bottom‐Up C₆₀ Fullerene Construction from a Fluorinated C₆₀H₂₁F₉ Precursor by Laser‐Induced Tandem Cyclization

Thermal Decomposition of the Fullerene Precursor C₆₀H₂₁F₉ Deposited on Graphite