C60F18O, the first characterised intramolecular fullerene ether

Boltalina, Olga V.; Vaissiere, Benoit de La; Fowler, Patrick W.; Hitchcock, Peter B.; Sandall, John P. B.; Troshin, Pavel A.; Taylor, Roger

doi:10.1039/b003753m

Cited by 60 publications

(47 citation statements)

References 12 publications

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“…A different alternative is to produce exohedral fullerene derivatives containing fluorine or chlorine atoms, which is a standard procedure in many laboratories. [9,10,[53][54][55] In contrast to endohedral derivatives, the synthesis of halogenated exohedral fullerenes always implies the formation of covalent bonds with the cage. Since halogen atoms preferentially form such bonds at AP sites, there is also an additional stabilization due to strain relaxation.…”

Section: Resultsmentioning

confidence: 98%

Stable Non‐IPR C₆₀ and C₇₀ Fullerenes Containing a Uniform Distribution of Pyrenes and Adjacent Pentagons

2008

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The most abundant fullerenes, C(60) and C(70), and all the pure carbon fullerenes larger than C(70), follow the isolated-pentagon rule (IPR). Non-IPR fullerenes containing adjacent pentagons (APs) have been stabilized experimentally in cases where, according to Euler's theorem, it is topologically impossible to isolate all the pentagons from each other. Surprisingly, recent experiments have shown that a few endohedral fullerenes, for which IPR structures are possible, are stabilized in non-IPR cages. We show that, apart from strain, the physical property that governs the relative stabilities of fullerenes is the charge distribution in the cage. This charge distribution is controlled by the number and location of APs and pyrene motifs. We show that, when these motifs are uniformly distributed in the cage and well-separated from one other, stabilization of non-IPR endohedral and exohedral derivatives, as well as pure carbon fullerene anions and cations, is the rule, rather than the exception. This suggests that non-IPR derivatives might be even more common than IPR ones.

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Section: Resultsmentioning

confidence: 98%

Stable Non‐IPR C₆₀ and C₇₀ Fullerenes Containing a Uniform Distribution of Pyrenes and Adjacent Pentagons

2008

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“…[7,[14][15][16] In case of C 60 Cl 30 , bonds like C10 À C11 (bond type e, see Schlegel diagram Figure 2, bottom) show a bent character despite the extreme bond length. Figure 6 shows the Laplacian distribution of the five-membered ring containing the C10 À C11 bond.…”

Section: à3mentioning

confidence: 98%

Bond Orders and Atomic Properties of the Highly Deformed Halogenated Fullerenes C₆₀F₁₈ and C₆₀Cl₃₀ Derived from their Charge Densities

Hübschle

Scheins

Weber

et al. 2007

Chemistry A European J

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The experimental charge densities of the halogenated C(60) fullerenes C(60)F(18) and C(60)Cl(30) were determined from high-resolution X-ray data sets measured with conventional Mo(Kalpha) radiation at 20 K for C(60)Cl(30) and with synchrotron radiation at 92 K for the fluorine compound. Bond topological and atomic properties were analyzed by using Bader's AIM theory. For the different C--C bonds, which vary in lengths between 1.35 and 1.70 A bond orders n between n=2 and significantly below n=1 were calculated from the bond topological properties at the bond critical points (BCP's). The low bond orders are seen for 5/6 bonds with each contributing carbon carrying a halogen atom. By integration over Bader's zero flux basins in the electron density gradient vector field atomic properties were also obtained. In contrast to free C(60), in which all carbon atoms have a uniform volume of 11 A(3) and zero charge, atomic volumes vary roughly between 5 and 10 A(3) in the halogenated compounds. Almost zero atomic charges are also found in the Cl derivative but a charge separation up to +/-0.8 e exists between C and F in C(60)F(18) due to the higher fluorine electronegativity, which is also seen in the electrostatic potential for which the electronegativity difference between carbon and fluorine, and the addition to one hemisphere of the fullerene cage leads to a strong potential gradient along the C(60)F(18) molecule. From the summation over all atomic volumes it follows that the halogen addition does not only lead to a dramatic distortion of the C(60) cage but also to a significant shrinkage of its volume.

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“…2, together with a peak downfield at d -75.7. Previously, peaks for fluorines adjacent to ether oxygens in the cage framework have been found at d -74.6/À77.9, À91.6/À115.8 and -94.6 [9]. The implication of the spectrum is therefore that oxygen has inserted into the cage to give oxahomo isomers of 2.…”

Section: 6 Min Eluentmentioning

confidence: 94%

“…The implication of the spectrum is therefore that oxygen has inserted into the cage to give oxahomo isomers of 2. Oxahomofullerenes have now been found not only with fluorofullerenes [9] and due to direct insertion of atmospheric oxygen in to FC-CF bonds, but with [60]-and [70]fullerenes themselves [10]. A 2D spectrum showed couplings of the kind found for 2 but the complexity of the spectrum precluded any detailed analysis at this stage.…”

Section: 6 Min Eluentmentioning

confidence: 94%

C60F14OFPh3, a fluoroxy derivative of C60F15Ph3; evidence for the presence of ‘missing’ fluorine through restricted rotation of a phenyl group

Darwish

Avent

Goldt

et al. 2004

Journal of Fluorine Chemistry

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C60F18O, the first characterised intramolecular fullerene ether

Abstract: A single-crystal X-ray structure determination of the main isomer of C 60 F 18 O shows it to be an intramolecular fullerene ether rather than an epoxide, and thus the first example of an oxa-homo[60]fullerene.

Cited by 60 publications

References 12 publications

Stable Non‐IPR C₆₀ and C₇₀ Fullerenes Containing a Uniform Distribution of Pyrenes and Adjacent Pentagons

Stable Non‐IPR C₆₀ and C₇₀ Fullerenes Containing a Uniform Distribution of Pyrenes and Adjacent Pentagons

Bond Orders and Atomic Properties of the Highly Deformed Halogenated Fullerenes C₆₀F₁₈ and C₆₀Cl₃₀ Derived from their Charge Densities

C60F14OFPh3, a fluoroxy derivative of C60F15Ph3; evidence for the presence of ‘missing’ fluorine through restricted rotation of a phenyl group

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C60F18O, the first characterised intramolecular fullerene ether

Abstract: A single-crystal X-ray structure determination of the main isomer of C 60 F 18 O shows it to be an intramolecular fullerene ether rather than an epoxide, and thus the first example of an oxa-homo[60]fullerene.

Cited by 60 publications

References 12 publications

Stable Non‐IPR C60 and C70 Fullerenes Containing a Uniform Distribution of Pyrenes and Adjacent Pentagons

Stable Non‐IPR C60 and C70 Fullerenes Containing a Uniform Distribution of Pyrenes and Adjacent Pentagons

Bond Orders and Atomic Properties of the Highly Deformed Halogenated Fullerenes C60F18 and C60Cl30 Derived from their Charge Densities

C60F14OFPh3, a fluoroxy derivative of C60F15Ph3; evidence for the presence of ‘missing’ fluorine through restricted rotation of a phenyl group

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Stable Non‐IPR C₆₀ and C₇₀ Fullerenes Containing a Uniform Distribution of Pyrenes and Adjacent Pentagons

Stable Non‐IPR C₆₀ and C₇₀ Fullerenes Containing a Uniform Distribution of Pyrenes and Adjacent Pentagons

Bond Orders and Atomic Properties of the Highly Deformed Halogenated Fullerenes C₆₀F₁₈ and C₆₀Cl₃₀ Derived from their Charge Densities