Isolation and characterisation of C60F4, C60F6, C60F8, C60F7CF3 and C60F2O, the smallest oxahomofullerene; the mechanism of fluorine addition to fullerenes

Boltalina, Olga V.; Darwish, Adam D.; Street, Joan M.; Taylor, Roger; Wei, Xian‐Wen

doi:10.1039/b108832g

Cited by 55 publications

(88 citation statements)

References 23 publications

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“…And only after particular measures were taken, the authors succeeded in separating lower fluorinated species C 60 F 2 , C 60 F 4 , C 60 F 6 , and C 60 F 8 [48,49] confirming adducts stability.…”

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confidence: 92%

Stepwise computational synthesis of fullerene C60 derivatives. Fluorinated fullerenes C60F2k

Sheka

2010

J. Exp. Theor. Phys.

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Abstract. The reactions of fullerene C 60 with atomic fluorine have been studied by unrestricted broken spin-symmetry Hartree-Fock (UBS HF) approach implemented in semiempirical codes based on AM1 technique. The calculations were focused on a sequential addition of fluorine atom to the fullerene cage following indication of the cage atom highest chemical susceptibility that is calculated at each step. The effectively-non-paired-electron concept of the fullerene atoms chemical susceptibility lays the foundation of the suggested computational synthesis. The obtained results are analyzed from energetic, symmetry, and the composition abundance viewpoints. A good fitting of the data to experimental findings proves a creative role of the suggested synthesis methodology.

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confidence: 92%

Stepwise computational synthesis of fullerene C60 derivatives. Fluorinated fullerenes C60F2k

Sheka

2010

J. Exp. Theor. Phys.

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“…Lewis acid promoted reactions of C 60 F 18 with aromatics proceed through an S N 1 mechanism; therefore, aromatic residues directly replace three fluorine atoms thus yielding triumphenes that have the same addition pattern as the parent C 60 F 18 . [11] In contrast, trannulenes have a very different addition pattern because their formation from C 60 F 18 is operated by a rare S N 2'' mechanism in which the reacting nucleophiles (carbon anions À CXA C H T U N G T R E N N U N G (COOR) 2 ) become attached at the d positions with respect to carbon atoms bearing the leaving fluorine atoms.…”

Section: Resultsmentioning

confidence: 98%

“…Triumphenes are isostructural and isoelectronic to the parent fluorofullerene C 60 F 18 , therefore, they have lemon-yellow colors both in solution and in the solid state. The absorption spectra of C 60 F 18 and representative examples of a triumphene and a trannulene are shown in Figure 2. …”

Section: Resultsmentioning

confidence: 99%

“…Two projections of 2 a are shown in Figure 3. It can be seen from these drawings that three organic addends in 2 a are attached near the fluorinated belt to those carbon atoms that bear three outlying fluorine atoms in C 60 F 18 . Therefore, compound 2 a (and presumably 2 b-e) is the first triumphene that comprises three aliphatic organic addends, which distinguishes it from previously synthesized triumphenes with three aryl groups.…”

Section: Wwwchemeurjorgmentioning

confidence: 97%

“…Therefore, compound 2 a (and presumably 2 b-e) is the first triumphene that comprises three aliphatic organic addends, which distinguishes it from previously synthesized triumphenes with three aryl groups. [11] Thus, thermal isomerization of trannulenes can be considered to be a convenient synthetic route for the preparation of novel triumphenes with aliphatic substituents that cannot be obtained directly from fluorofullerene C 60 F 18 .…”

Section: Wwwchemeurjorgmentioning

confidence: 99%

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The Remarkable Chemistry of Trannulenes: Green Fluorinated Fullerenes with Unconventional Aromaticity

Khakina

Troyanov

Peregudov

et al. 2010

Chemistry A European J

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We report the first reaction of trannulenes involving their thermal isomerization to a new class of compounds termed "triumphenes". The thermodynamically controlled conversion of trannulenes into triumphenes is accompanied by an unprecedented migration of three organic addends from one hemisphere of the fullerene cage to another. The reaction products, bearing aliphatic substituents, might find applications in materials science as strong electron acceptors due to the presence of fifteen electron-withdrawing fluorine atoms in their molecular framework. It was revealed that the isomerization of trannulenes can be affected by the presence of unsaturated compounds in the reaction mixture. Heating of trannulenes C(60)F(15)R(3) with C(60), C(70), anthracene, or pentacene at reflux in 1,2-dichlorobenzene yields fluorinated derivatives C(60)F(14)R(2)A, which possess a fused cyclic addend A. The products of this reaction have "triumphene-type" addition patterns and seem to be formed through an unprecedented sequence of elimination, addition, and isomerization steps. The molecular structure of a representative triumphene was proven unambiguously by X-ray single-crystal diffraction analysis and by NMR spectroscopy. The reactions revealed here open up numerous opportunities for chemical derivatization of fluorinated fullerenes. This method promises to provide a new path towards valuable photoactive materials and a new generation of fullerene-based compounds that are suitable for biomedical applications.

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Manganese Trifluoride

Burley¹,

Taylor²

2004

Encyclopedia of Reagents for Organic Synthesis

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Isolation and characterisation of C60F4, C60F6, C60F8, C60F7CF3 and C60F2O, the smallest oxahomofullerene; the mechanism of fluorine addition to fullerenes

Cited by 55 publications

References 23 publications

Stepwise computational synthesis of fullerene C60 derivatives. Fluorinated fullerenes C60F2k

Stepwise computational synthesis of fullerene C60 derivatives. Fluorinated fullerenes C60F2k

The Remarkable Chemistry of Trannulenes: Green Fluorinated Fullerenes with Unconventional Aromaticity

Manganese Trifluoride

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