Isolation, characterization, and chemical reactions of fullerenes

Taylor, Roger; Avent, Anthony G.; Birkett, P. R.; Dennis, T. John S.; Hare, Jonathon; Hitchcock, Peter B.; Holloway, John H.; Hope, Eric G.; Kroto, Harold W.; Langley, G. John; Meidine, Mohamed F.; Parsons, Jonathan P.; Walton, D. R. M.

doi:10.1351/pac199365010135

Cited by 15 publications

(5 citation statements)

References 7 publications

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“…Corannulene has 13 C NMR chemical shifts of 135.8, 130.8, and 127.1 ppm, which are consistent with the C Cata and the C ar-PC definitions. Meanwhile, the 13 C chemical shifts of fullerenes , appear in the region of the NMR spectrum attributed to the C Cata and the C ar-AS . It is possible that some of the signals seen in the C Cata and the C ar-AS regions of the PPS and also of the PPI NMR spectra are from similar structural features.…”

Section: Resultsmentioning

confidence: 99%

Optimization of ¹H and ¹³C NMR Methods for Structural Characterization of Acetone and Pyridine Soluble/Insoluble Fractions of a Coal Tar Pitch

et al. 2008

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Supporting information[s1] Solvents for NMR NMP: When NMP (Rathburn Chemicals, UK. Peptide synthesis grade) was used as solvent in proton NMR, the TKS peak area was found to be roughly 10% larger than when Quinoline was used. This was attributed to the overlap of the NMP and TKS peaks, artificially increasing the peak area of the TKS. In addition, as the NMP used was undeuterated the signal from the NMP can cause the data file, on Bruker machines, to overload with a significant loss of data, and/or cause ringing in the baseline. This is probably caused by a phenomenon known as "radiation damping" which occurs when there are very strong signals present, i.e. the NMP protons. A pulse saturation method [ZGPS micro-programme] was employed to suppress the signal from the NMP proton peaks, which resolved these issues. It would be possible to use deuterated NMP (Cambridge Isotopes, USA) to avoid these issues, although at considerably higher expense; no sources of deuterated quinoline could be found. Quinoline:The quinoline used in this investigation (Fisher Scientific Ltd, UK, synthetic quinoline 99%, part number: 41879-0250) had trace impurities present which gave a small but significant signal in the aliphatic region of the NMR spectra. Numerous sources of quinoline were tested, however, all were found to contain similar if not worse levels of impurities. No information was available on the form of these trace impurities, and repeated distillation was insufficient to remove this material. Therefore the *Values in brackets were calculated excluding the ET data. N/A, not applicable.

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Section: Resultsmentioning

confidence: 99%

Optimization of ¹H and ¹³C NMR Methods for Structural Characterization of Acetone and Pyridine Soluble/Insoluble Fractions of a Coal Tar Pitch

et al. 2008

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“…Fullerenes with other numbers of carbons are impossible to have all the pentagons isolated in the carbon cage, thus they are called unconventional fullerenes or non-IPR fullerenes, which are believed to be labile and difficult to synthesize. In fact, most of the several stable fullerene isomers that had been isolated are satisfying IPR. For applications, fullerenes and their derivatives are potential new agents and materials for molecular electronics, nanoprobes, superconductors, and nonlinear optics.…”

Section: Introductionmentioning

confidence: 99%

Structures, Electronic Properties, Spectroscopies, and Hexagonal Monolayer Phase of a Family of Unconventional Fullerenes C₆₄X₄ (X = H, F, Cl, Br)

Yan

Zheng

2006

J. Phys. Chem. C

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A systematic first-principles study within density functional theory on the geometrical structures and electronic properties of unconventional fullerene C 64 and its derivatives C 64 X 4 (X = H, F, Cl, Br) has been performed. By searching through all 3465 isomers of C 64 , the ground state of C 64 is found to be spherical shape with D 2 symmetry, which differs from the parent cage of the recently synthesized C 64 H 4 that is pear-shaped with C 3v symmetry. We found that the addition of the halogen atoms like F, Cl, Br to the pentagon-pentagon fusion vertex of C 64 cage could enhance the stability, forming the unconventional fullerenes C 64 X 4 . The Mulliken charge populations, LUMO-HOMO gap energies and density of states are calculated, showing that different halogen atoms added to C 64 will cause remarkably different charge populations of the C 64 X 4 molecule; the chemical deriving could enlarge the energy gaps and affect the electronic structures distinctly. It is unveiled that C 64 F 4 is even more stable than C 64 H 4 , as the C-X bond energy of the former is higher than that of the latter. The computed spectra of C 64 H 4 molecules agree well with the experimental data; the IR, Raman, NMR spectra of C 64 X 4 (X = F, Cl, Br) are also calculated to stimulate further experimental investigations. Finally, it is uncovered by total energy calculations that C 64 X 4 could form a stable hexagonal monolayer.

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“…65 Hoping to reduce the addition level, we decided to use a higher concentration of fullerene relative to bromine, and chose CS 2 as solvent since it dissolves relatively large amounts of fullerenes; this produced C 60 Br 8 . 67 Conjectured mechanism for rearrangement of C 60 Br 6 into C 60 Br 8 (see text). 64 Both derivatives yielded singlecrystal X-ray structures Fig.…”

Section: Formation Of C 60 Br 24 C 60 Br 8 and C 60 Brmentioning

confidence: 99%

Surprises, Serendipity, and Symmetry in Fullerene Chemistry

2000

Synlett

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Isolation, characterization, and chemical reactions of fullerenes

Abstract: Extension of the chromatographic work that led to the first isolation of pure G o and 0 0 has resulted h the isolation and characterisation of c76 and three isomers of c78.

Cited by 15 publications

References 7 publications

Optimization of ¹H and ¹³C NMR Methods for Structural Characterization of Acetone and Pyridine Soluble/Insoluble Fractions of a Coal Tar Pitch

Optimization of ¹H and ¹³C NMR Methods for Structural Characterization of Acetone and Pyridine Soluble/Insoluble Fractions of a Coal Tar Pitch

Structures, Electronic Properties, Spectroscopies, and Hexagonal Monolayer Phase of a Family of Unconventional Fullerenes C₆₄X₄ (X = H, F, Cl, Br)

Surprises, Serendipity, and Symmetry in Fullerene Chemistry

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Isolation, characterization, and chemical reactions of fullerenes

Abstract: Extension of the chromatographic work that led to the first isolation of pure G o and 0 0 has resulted h the isolation and characterisation of c76 and three isomers of c78.

Cited by 15 publications

References 7 publications

Optimization of 1H and 13C NMR Methods for Structural Characterization of Acetone and Pyridine Soluble/Insoluble Fractions of a Coal Tar Pitch

Optimization of 1H and 13C NMR Methods for Structural Characterization of Acetone and Pyridine Soluble/Insoluble Fractions of a Coal Tar Pitch

Structures, Electronic Properties, Spectroscopies, and Hexagonal Monolayer Phase of a Family of Unconventional Fullerenes C64X4 (X = H, F, Cl, Br)

Surprises, Serendipity, and Symmetry in Fullerene Chemistry

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Optimization of ¹H and ¹³C NMR Methods for Structural Characterization of Acetone and Pyridine Soluble/Insoluble Fractions of a Coal Tar Pitch

Optimization of ¹H and ¹³C NMR Methods for Structural Characterization of Acetone and Pyridine Soluble/Insoluble Fractions of a Coal Tar Pitch

Structures, Electronic Properties, Spectroscopies, and Hexagonal Monolayer Phase of a Family of Unconventional Fullerenes C₆₄X₄ (X = H, F, Cl, Br)