[60]Fullerenoacetyl Chloride as a Versatile Precursor for Fullerene Derivatives:  Efficient Ester Formation with Various Alcohols

Itô, Hiroshi; Tada, Tomoyuki; Sudo, Masafumi; Ishida, Yasuhiro; Hino, Taro; Saigo, Kazuhiko

doi:10.1021/ol034793g

Cited by 33 publications

(19 citation statements)

References 12 publications

(13 reference statements)

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“…Two different functionalised fullerenes, namely, C60-fullerenoacetic acid [38] and C60-epoxyfullerenes, were utilised [39]. According to the values obtained by elemental analysis of aminosilica, the amount of amino groups were calculated (0.0032 mmol/m 2 ).…”

Section: C60-fullerene-bound Silicamentioning

confidence: 99%

Fast, noninvasive and simultaneous near‐infrared spectroscopic characterisation of physicochemical stationary phases' properties: From silica particles towards monoliths

Petter

Heigl

Bonn

et al. 2008

J of Separation Science

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The design of novel stationary phases is a permanent demanding challenge in chromatographic separation science to enable analysis with enhanced selectivity, specificity and speed. Therefore, the characterisation of chemical and physical properties is next to calculation of chromatographic parameters essential. Conventionally, chemical parameters including surface coverage are determined by burning combustion or frontal analysis, physical parameters including particle size, pore size, pore volume and surface area are determined by SEM, mercury intrusion porosimetry (MIP) and Brunauer-Emmett-Teller (BET). All these methods are time consuming, invasive and require besides special equipment some special trained laboratory staff. Therefore, we introduced near-infrared spectroscopy (NIRS) as a noninvasive, easy-to-handle technology with wavenumber ranging from 4000 to 10,000 cm(-1) enabling analysis within only a few seconds at higher precision than the conventional methods. Investigated materials comprise porous and nonporous silica gel, carbon-based nanomaterials (fullerenes), polymer beads and monoliths. Different carriers themselves and their kind of derivatisations (RP, normal-phase, ion-exchanger, IMAC (immobilised metal affinity chromatography), affinity) can be determined by applying principal component analysis (PCA) of recorded spectra. Partial least square regression (PLSR) enables the determination of particle size, pore size, pore volume, porosity, total porosity and surface area with one single measurement. For the optimised design of well-defined polymer beads and monoliths, real-time in situ monitoring to control, e. g. particle and pore sizes as well as monomer content during the polymerisation process, can be extremely helpful. In this article, the advantages of this fast, noninvasive high-throughput NIRS methods are summarised, discussed in detail and different applications of the individual characterised materials are shown.

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Section: C60-fullerene-bound Silicamentioning

confidence: 99%

Fast, noninvasive and simultaneous near‐infrared spectroscopic characterisation of physicochemical stationary phases' properties: From silica particles towards monoliths

Petter

Heigl

Bonn

et al. 2008

J of Separation Science

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“…The mixture was stirred at room temperature for 8 h. The product consisting of mono‐, di‐ and tri‐adduct was separated by flash column chromatography using silica gel 60, and toluene as mobile phase. The purified t ‐butyl [60]fullerenoacetate gave a yield of 360 mg (0.43 mmol) which was further hydrolyzed with p ‐toluenesulfonic acid in the presence of dry toluene 30. The brown solid (C60‐fullerenoacetic acid) was filtered and washed with toluene and water.…”

Section: Methodsmentioning

confidence: 99%

Laser desorption/ionization mass spectrometric analysis of small molecules using fullerene‐derivatized silica as energy‐absorbing material

et al. 2010

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In spite of the growing acceptance of matrix-assisted laser desorption/ionization time-of-flight mass spectrometry for the analysis of a wide variety of compounds, including polymers and proteins, its use in analyzing low-molecular-weight molecules (<1000 m/z) is still limited. This is mainly due to the interference of matrix molecules in the low-mass range. Here the derivatized fullerenes covalently bound to silica particles with different pore sizes are applied as thin layer for laser desorption/ionization (LDI) mass spectrometric analysis. Thus, an interference of intrinsic matrix ions can be eliminated or minimized in comparison with the state-of-the-art weak organic acid matrices. The desorption/ionization ability of the developed fullerene-silica materials depends on the applied laser power, sample preparation and pore size of the silica particles. Thus, fullerene-silica serves as an LDI support for mass spectrometric analysis of molecules (<1500 Da). The performance of the fullerene-silica is demonstrated by the mass analysis of variety of small molecules such as carbohydrates, amino acids, peptides, phospholipids and drugs.

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“…24 Fabrication of Poly(p-methylstyrene-co-1,2-bis(p-vinylphenyl)ethane) (MSt/BVPE) Capillary Columns. Monolithic MSt/ BVPE capillary columns were produced by thermally initiated free radical polymerization of methylstyrene (MSt) and 1,2-bisp(vinylphenyl)ethane (BVPE), which was synthesized by Grignard dimerization of p-vinylbenzyl choride as described elsewhere.…”

Section: Methodsmentioning

confidence: 99%

A New Analytical Material-Enhanced Laser Desorption Ionization (MELDI) Based Approach for the Determination of Low-Mass Serum Constituents Using Fullerene Derivatives for Selective Enrichment

et al. 2006

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60]fullerene derivatives (dioctadecyl methano[60]fullerene, [60]fullerenoacetic acid, and IDA-[60]fullerene) were prepared and subjected to a comprehensive characterization study including protein binding properties and capacity. These fullerene derivatives were successfully applied as material-enhanced laser desorption/ionization (MELDI) carrier materials. It is shown that diverse functionalities result in characteristic human serum peak patterns (m/z 2000-20 000) in terms of signal intensity as well as the number of detectable masses. In addition, the fullerene derivatives clearly provided differences in the low molecular weight mass region (m/z 1000-4000) after elution of the adsorbed serum constituents, and [60]fullerenoacetic acid was the most effective carrier material. Novel high-speed, monolithic, high-resolution capillary columns, prepared by thermally initiated copolymerization of methylstyrene (MSt) and 1,2-bis(p-vinylphenyl)ethane (BVPE) were employed for eluate separation and target spotting. Thus, serum compounds in the low-mass range were successfully fractionated and subjected to MALDI-MS/MS analysis. This contribution, hence, proposes a new "top-down" strategy for proteome research enabling protein profiling as well as biomarker identification in the low-mass range using selective enrichment, high-resolution separation, and offline MALDI-MS/MS evaluation.

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[60]Fullerenoacetyl Chloride as a Versatile Precursor for Fullerene Derivatives: Efficient Ester Formation with Various Alcohols

Cited by 33 publications

References 12 publications

Fast, noninvasive and simultaneous near‐infrared spectroscopic characterisation of physicochemical stationary phases' properties: From silica particles towards monoliths

Fast, noninvasive and simultaneous near‐infrared spectroscopic characterisation of physicochemical stationary phases' properties: From silica particles towards monoliths

Laser desorption/ionization mass spectrometric analysis of small molecules using fullerene‐derivatized silica as energy‐absorbing material

A New Analytical Material-Enhanced Laser Desorption Ionization (MELDI) Based Approach for the Determination of Low-Mass Serum Constituents Using Fullerene Derivatives for Selective Enrichment

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