High-performance liquid chromatography of C60, C70, and higher fullerenes on tetraphenylporphyrin-silica stationary phases using strong mobile phase solvents

Xiao, Jie; Meyerhoff, Mark E.

doi:10.1016/0021-9673(95)00560-a

Cited by 54 publications

(35 citation statements)

References 37 publications

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“…Any application, however, is limited in origin by tedious solidliquid extractions (usually in toluene) and time-expensive chromatographic separations [6][7][8][9][10][11][12][13][14][15] . More recently, the host-guest chemistry of molecular containers has been explored to encapsulate fullerenes 16 .…”

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confidence: 99%

Sponge-like molecular cage for purification of fullerenes

et al. 2014

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Since fullerenes are available in macroscopic quantities from fullerene soot, large efforts have been geared toward designing efficient strategies to obtain highly pure fullerenes, which can be subsequently applied in multiple research fields. Here we present a supramolecular nanocage synthesized by metal-directed self-assembly, which encapsulates fullerenes of different sizes. Direct experimental evidence is provided for the 1:1 encapsulation of C 60 , C 70 , C 76 , C 78 and C 84 , and solid state structures for the host-guest adducts with C 60 and C 70 have been obtained using X-ray synchrotron radiation. Furthermore, we design a washingbased strategy to exclusively extract pure C 60 from a solid sample of cage charged with a mixture of fullerenes. These results showcase an attractive methodology to selectively extract C 60 from fullerene mixtures, providing a platform to design tuned cages for selective extraction of higher fullerenes. The solid-phase fullerene encapsulation and liberation represent a twist in host-guest chemistry for molecular nanocage structures.

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confidence: 99%

Sponge-like molecular cage for purification of fullerenes

et al. 2014

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“…Among the separation techniques, liquid chromatography (LC) is the most effective and its applicability for the separation of fullerenes has been investigated since the 1990s [104][105][106][107][108] . Table 4 summarizes the LC methods reported in the literature for the analysis of this family of compounds in complex matrices.…”

Section: Liquid Chromatographymentioning

confidence: 99%

“…Among the other stationary phases reported for the analysis of pristine fullerenes [125,126] the ones based on phenylporphyrin immobilized on silica, such as tetraphenylporphyrin-silica [108] and hydroxyphenyltriphenylporphyrin-silica [127] provide very good selectivity and efficiency. However, the use of these columns is limited by the high cost of phenylporphyrin materials.…”

Section: Liquid Chromatographymentioning

confidence: 99%

“…Other ionisation techniques such as matrix-assisted laser desorption ionisation (MALDI) have also been proposed for the characterisation of pristine fullerenes [108] and fullerol [111] , although the utility of MALDI for quantitative analysis is limited. For instance, Xiao et al [108] used MALDI-TOF-MS to identify several fullerenes, from C 76 to C 94 in a pyridine extract of crude soot .…”

Section: Detectionmentioning

confidence: 99%

“…For instance, Xiao et al [108] used MALDI-TOF-MS to identify several fullerenes, from C 76 to C 94 in a pyridine extract of crude soot . More recently, Chao et al [111] used MALDI-TOF-MS to characterise fullerol using 2,5-dihydrobenzoic acid as matrix.…”

Section: Detectionmentioning

confidence: 99%

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Characterisation and determination of fullerenes: A critical review

Astefanei

Núñez

Galcerán

2015

Analytica Chimica Acta

165

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Highlights Methodologies for fullerene aggregate characterization are discussed.  Chromatographic and electrophoretic techniques for fullerene analysis are presented.  Accurate identification and detection of fullerenes by LC-MS is critically reviewed. Graphical abstract AbstractA prominent sector of nanotechnology is occupied by a class of carbon-based nanoparticles known as fullerenes. Fullerene particle size and shape impact in how easily these particles are transported into and throughout the environment and living tissues. Currently, there is a lack of adequate methodology for their size and shape characterisation, identification and quantitative detection in environmental and biological samples. The most commonly used methods for their size measurements (aggregation, size distribution, shape, etc.), the effect of sampling and sample treatment on these characteristics and the analytical methods proposed for their determination in complex matrices are discussed in this review. For the characterisation and analysis of fullerenes in real samples, different analytical techniques including microscopy, spectroscopy, flow field-flow fractionation, electrophoresis, light scattering, liquid chromatography and mass spectrometry have been reported. The existing limitations and knowledge gaps in the use of these techniques are discussed and the necessity to hyphenate complementary ones for the accurate characterisation, identification and quantitation of these nanoparticles is highlighted.

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Interstitial Accommodation of C₆₀ in a Surface‐Supported Supramolecular Network

et al. 2006

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The controlled supramolecular assembly of nanostructures from molecular building blocks relies on selective and directional intermolecular interactions. [1] Recently, this concept has been applied to the controlled formation of surface-supported architectures, [2,3] and a rich variety of molecular nanostructures such as clusters, wires, and extended networks have been directly characterized by using scanning tunneling microscopy (STM). [4][5][6][7] In particular, the controlled assembly of porous supramolecular networks on surfaces has attracted much attention because of the ability of these networks to act as templates for the accommodation of guest molecules. [5,[8][9][10][11] These systems are expected to have potential applications in molecular recognition, selective catalysis, and molecular storage. Here, we demonstrate that a flexible porous network formed by the selective assembly of a porphyrin derivative on Au(111) is a suitable nanoscale template for accommodating large guest molecules. The initial network is characterized by a close-packed arrangement of the porphyrin molecules without any pores; however, as we demonstrate here, the formation of nanopores is induced by the adsorption of C 60 so as to accommodate these large guest molecules. The supramolecular network is formed by the selective assembly of 5,15-bis(4-carboxyphenyl)-10,20-bis(3,5-di-t-butylphenyl)porphyrin (trans-BCaTBPP) ( Fig. 1) on a Au(111) surface.[8] Figure 1a shows the morphology of the obtained supramolecular network, indicating that the entire Au(111) substrate has been covered with trans-BCaTBPP molecules. The bright rows seen in this image correspond to molecules forming a second layer. The ground-state conformation of trans-BCaTBPP is altered by molecule-substrate interactions upon adsorption onto the Au (111) surface, forcing the phenyl-porphyrin single bonds to be rotated. The rotated di-t-butylphenyl (t-BP) groups and the central porphyrin can be clearly observed in the high-resolution STM image shown in Figure 1b. As reported previously, [8,12] the dihedral angle between the porphyrin and phenyl rings is estimated to be about 20°, as compared to the 60°-90°dihedral angles expected for the ground-state conformation. The supramolecular network is characterized by sequential hydrogen bonding between the carboxyphenyl groups of trans-BCaTBPP, as depicted schematically in Figure 1c. Within the wires, the inter-porphyrin distance is estimated to be about 2.1 nm, which matches very well with the ideal hydrogen-bonding distance (2.24 nm) derived from ab initio molecular orbital calculations.[12] The long and straight supramolecular wires are densely aggregated on the surface and the interwire distance is almost 1.4 nm. The straight nanowires extend at angles of +16.1°or -16.1°f rom [112], and the three-fold symmetry of the Au(111) surface yields a total of six equivalent growth directions for the wires. Nevertheless, we have obtained single domain structures extending over an entire terrace by optimizing the growth temperature.[1...

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High-performance liquid chromatography of C60, C70, and higher fullerenes on tetraphenylporphyrin-silica stationary phases using strong mobile phase solvents

Cited by 54 publications

References 37 publications

Sponge-like molecular cage for purification of fullerenes

Sponge-like molecular cage for purification of fullerenes

Characterisation and determination of fullerenes: A critical review

Interstitial Accommodation of C₆₀ in a Surface‐Supported Supramolecular Network

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High-performance liquid chromatography of C60, C70, and higher fullerenes on tetraphenylporphyrin-silica stationary phases using strong mobile phase solvents

Cited by 54 publications

References 37 publications

Sponge-like molecular cage for purification of fullerenes

Sponge-like molecular cage for purification of fullerenes

Characterisation and determination of fullerenes: A critical review

Interstitial Accommodation of C60 in a Surface‐Supported Supramolecular Network

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Interstitial Accommodation of C₆₀ in a Surface‐Supported Supramolecular Network