Application of sulfur as a matrix for laser desorption/ionization in the characterization of halogenated fullerenes

Streletskiy, Alexey V.; Kouvitchko, Igor V.; Esipov, S. E.; Boltalina, Olga V.

doi:10.1002/rcm.551

Cited by 34 publications

(37 citation statements)

References 19 publications

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“…[21] There have been some reports of the preparation of samples with the composition C 60 Cl 24 . Heating of C 60 in a chlorine flow was claimed to yield C 60 Cl 24 , [16,22] but the compo-sitions of these samples were determined only by elemental analysis, thermogravimetry, or both.…”

Section: Synthesis Bromidesmentioning

confidence: 99%

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Synthesis and Structures of Fullerene Bromides and Chlorides

Troyanov

Kemnitz

2005

Eur J Org Chem

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Halogenated fullerenes have been subjects of intensive investigations since the discovery of fullerene, because of their possible further derivatization. This paper reviews the synthesis and molecular structures of fullerene bromides and chlorides, covering earlier work in this field and progress in synthetic methods developed by the authors. The use of inorganic chlorides and oxychlorides for the chlorination of fullerenes allowed the preparation of new compounds that have been fully characterized by single-crystal X-ray diffraction and IR spectroscopy and confirmed by theoretical calcula-

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Section: Synthesis Bromidesmentioning

confidence: 99%

“…[10][11][12][13] Lower [60]fullerene bromides are insoluble in organic solvents, whilst low solubility in liquid bromine has been reported for C 60 Br 24 . The IR spectra of the [60]fullerene bromides have been published both in earlier [10] and in more recent papers.…”

Section: Synthesis Bromidesmentioning

confidence: 99%

Synthesis and Structures of Fullerene Bromides and Chlorides

Troyanov

Kemnitz

2005

Eur J Org Chem

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“…Keywords: fullerenes · iodine · mass spectrometry · Raman spectroscopy will depend on the availability of 10 + milligram batches of a variety of pure chlorofullerenes with specific compositions and structures. For this reason, we have started a systematic study of fullerene chlorination reactions and have continued to develop Raman and mass spectrometry [18] procedures for the analysis of chlorofullerenes. This paper, the first in a series, describes an improved, rapid method for the preparation of 150 + mg batches of C 60 Cl 6 with 90 % yield/purity (HPLC integrated intensity).…”

Section: Introductionmentioning

confidence: 99%

“…Scheme 1 shows a number of plausible gas-phase reactions that might form the C 60 Cl 5 À fragment ion and the C 60 Cl 7 À adduct ion (the Cl À atomic ion was an abundant species in the low-mass region of the spectrum). We recently observed adduct-ion formation in an LDI/MALDI-MS study of the pure fluorofullerene C 60 F 18 . In addition to the C 60 F 18 À molecular ion and the C 60 F 17 À fragment ion, the C 60 F 19 À adduct ion was also observed (its intensity was 10 % of the intensity of the molecular ion).…”

mentioning

confidence: 98%

“…Samples 1, 2, and 3 were prepared under the same conditions reported in refs. [5], [20], and [12], respectively; see Table 1 FAB [20] and MALDI [18,29] methods of ionization resulted in substantial fragmentation (i.e., loss of many chlorine atoms) when the substrates were chlorofullerenes with more than 24 chlorine atoms. Chlorofullerenes with low chlorine content, such as C 60 Cl 6 , were found to undergo complete C-Cl fragmentation under MALDI conditions to produce only chlorine-free ions such as C 60 + .…”

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Seven‐Minute Synthesis of Pure C_s‐C₆₀Cl₆ from [60]Fullerene and Iodine Monochloride: First IR, Raman, and Mass Spectra of 99 mol % C₆₀Cl₆

Kuvychko

Streletskii

Popov

et al. 2005

Chemistry A European J

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Three previously reported procedures for the synthesis of pure C(s)-C60Cl6 from C60 and ICl dissolved in benzene or 1,2-dichlorobenzene were shown to actually yield complex mixtures of products that contain, at best, 54-80% C(s)-C60Cl6 based on HPLC integrated intensities. MALDI mass spectrometry was used for the first time to identify other components of the reaction mixtures. An improved synthetic procedure was developed for the synthesis of about 150 mg batches of chlorofullerenes containing 90% C(s)-C60Cl6 based on HPLC intensities. The optimum reaction time was decreased from several days to seven minutes. Small amounts of the product were purified by HPLC (toluene eluent) to 99% purity. The pure compound C(s)-C60Cl6 is stable for at least three months as a solvent-free powder at 25 degrees C. The Raman, far-IR, and MALDI mass spectra of pure C(s)-C60Cl6 are reported for the first time. The Raman and far-IR spectra, the first reported for any C60Cl(n) chlorofullerene, were used to carry out a vibrational analysis of C(s)-C60Cl6 at the DFT level of theory.

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Fullerenes

Li¹,

Wang²

2013

Kirk-Othmer Encyclopedia of Chemical Technology

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Fullerenes are a class of three‐dimensional all‐carbon hollow molecules containing a conjugated n system and are sometimes referred to as the “third form of carbon”. Each fullerene Cn consists of an even number of carbon atoms and represents a closed‐cage structure with 12 pentagons and (n–20)/2 hexagons. The isolated pentagon rule is an important principle to determine the stability of fullerene cages. [60]Fullerene (C60) has a truncated icosahedral spherical structure with 20 hexagons and 12 pentagons. [70]Fullerene (C70) is a kiwi‐like ellipsoidal molecule and its structure contains an additional equatorial band of 10 carbons relative to that of C60. Fullerenes containing > 70 atoms are known as “higher fullerenes”. Unlike the other forms of carbon, fullerenes are soluble and thus can undergo a wide range of chemical reactions. The main chemical reactions of fullerenes are nucleophilic additions, cycloadditions, and radical additions. The hollow cavities of fullerenes can enclose a wide variety of atoms, molecules, or metal clusters, and the class of fullerenes are named as endohedral fullerenes. In addition, the replacement of one or more carbons of the fullerene cage by other non‐carbon atoms such as nitrogen can lead to heterofullerenes. Fullerene derivatives bearing electrondonor groups have been investigated because of the potential for conversion of light into electricity. Some alkali metal‐doped fullerenes show the interesting superconducting properties. Although fullerenes are insoluble in water, some derivatives are very soluble and this has led to investigations of biological properties.

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Application of sulfur as a matrix for laser desorption/ionization in the characterization of halogenated fullerenes

Cited by 34 publications

References 19 publications

Synthesis and Structures of Fullerene Bromides and Chlorides

Synthesis and Structures of Fullerene Bromides and Chlorides

Seven‐Minute Synthesis of Pure C_s‐C₆₀Cl₆ from [60]Fullerene and Iodine Monochloride: First IR, Raman, and Mass Spectra of 99 mol % C₆₀Cl₆

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Application of sulfur as a matrix for laser desorption/ionization in the characterization of halogenated fullerenes

Cited by 34 publications

References 19 publications

Synthesis and Structures of Fullerene Bromides and Chlorides

Synthesis and Structures of Fullerene Bromides and Chlorides

Seven‐Minute Synthesis of Pure Cs‐C60Cl6 from [60]Fullerene and Iodine Monochloride: First IR, Raman, and Mass Spectra of 99 mol % C60Cl6

Fullerenes

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Seven‐Minute Synthesis of Pure C_s‐C₆₀Cl₆ from [60]Fullerene and Iodine Monochloride: First IR, Raman, and Mass Spectra of 99 mol % C₆₀Cl₆