Synthesis and Structures of Fullerene Bromides and Chlorides

Troyanov, Sergey I.; Kemnitz, Erhard

doi:10.1002/ejoc.200500369

Cited by 39 publications

(32 citation statements)

References 53 publications

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“…For example, theoretical calculations for non‐IPR C 60 Cl 8 predict it to be 1.4 eV lower in energy than the most stable octachloride of I h ‐C 60 8. Nevertheless, chlorination of C 60 with SbCl 5 under the similar conditions as reported is known to yield only IPR C 60 Cl 24 and C 60 Cl 30 molecules 15. Chlorination of C 70 ,16 C 78 ,17 and C 90 18 also leaves the σ networks of their carbon cages intact; the same applies to a different technique of chlorination of C 76 14 and C 80 19 at lower temperatures.…”

Section: Methodsmentioning

confidence: 78%

Fusing Pentagons in a Fullerene Cage by Chlorination: IPR D₂‐C₇₆ Rearranges into non‐IPR C₇₆Cl₂₄

et al. 2009

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Eine spektakuläre Gerüstumlagerung des C76‐Fullerenkäfigs resultiert aus der Chlorierung von D2‐C76 zu C76Cl24 (siehe Struktur: C grau, Cl grün; orangefarbene Bindungen zeigen Fünfringe an), dessen Kohlenstoffgerüst merklich abgeflacht ist und gegen die Regel der isolierten Fünfringe verstößt. Der Übergang umfasst vermutlich sieben Stone‐Wales‐Umlagerungen, die durch die Chlorierung deutlich erleichtert werden.

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Section: Methodsmentioning

confidence: 78%

Fusing Pentagons in a Fullerene Cage by Chlorination: IPR D₂‐C₇₆ Rearranges into non‐IPR C₇₆Cl₂₄

et al. 2009

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“…For more detailed information, see also the review by Troyanov and Kemnitz. [47] For C 76 Cl 18 , X-ray analysis demonstrated that the sp 2 -hybridized carbon atoms form a rather extended "aromatic girdle," which consists of 14 sixmembered cycles that form a helix in the same direction as the chlorine atoms. For C 80 Cl 12 , X-ray analysis demonstrated that the addition pattern of chlorine atoms has a notable feature, namely, the most pyramidal carbon atoms are not attacked during chlorination, although in other cases they have been found to be the most reactive ones.…”

Section: Electronic Rulesmentioning

confidence: 99%

“…Recently, many fullerene derivatives have been synthesized and characterized, such as C 76 Cl 18 ,41 C 80 Cl 12 ,42 C 60 Cl 30 ,43 and C 60 Cl 24 ,44 C 70 Cl 28 ,45 and C 76 Cl 34 46 by the use of this chemical‐synthesis method. For more detailed information, see also the review by Troyanov and Kemnitz 47. For C 76 Cl 18 , X‐ray analysis demonstrated that the sp 2 ‐hybridized carbon atoms form a rather extended “aromatic girdle,” which consists of 14 six‐membered cycles that form a helix in the same direction as the chlorine atoms.…”

Section: Fullerene Derivativesmentioning

confidence: 99%

Geometrical and Electronic Rules in Fullerene‐Based Compounds

Gan

Pan

et al. 2011

Chemistry An Asian Journal

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The discovery of buckminsterfullerene C(60) opened up a new scientific area and stimulated the development of nanoscience and nanotechnology directly. Fullerene science has since emerged to include fullerenes, endohedral fullerenes (mainly metallofullerenes), exofullerenes, and carbon nanotubes as well. Herein, we look back at the development of fullerene science from the perspective of epistemology by highlighting the proposed main rules or criteria for understanding and predicting the structures and stability of fullerene-based compounds. We also point out that a rule or criterion may contribute significantly to the corresponding discipline and suggest that two unsolved issues in fullerene science are the addition patterns of fullerene derivatives and the structures and stability of nonclassical fullerenes.

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“…Higher chlorides can be produced by using stronger chlorinating agents such as Cl 2 or some inorganic chlorides (ICl, SbCl 5 etc.) at higher temperature 16. For instance, recently chlorination of the mixture of higher fullerenes with SbCl 5 resulted in isolation and structural characterization of C 90 Cl 32 17.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Structure of a Highly Chlorinated C₇₈: C₇₈(2)Cl₃₀

Troyanov¹,

Tamm²,

Chen³

et al. 2009

Zeitschrift anorg allge chemie

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A Highly chlorinated C 78 fullerene, C 78 (2)Cl 30 , has been obtained by the reaction of the isomer C 78 (2) with SbCl 5 in ampoules at 330-340 °C. Single crystal structure determination revealed that the C 2v -C 78 IntroductionFullerene halides were among the first structurally investigated fullerene derivatives [1]. On the one hand, they can serve as intermediates for further derivatization of fullerenes. On the other hand, they sometimes facilitate characterization of the connectivity patterns of higher fullerenes. Chlorides of a given fullerene comprise a range of compositions, which lies between those of bromides and fluorides. For example, the known chlorides of C 60 contain 6 to 30 attached Cl atoms [2][3][4][5], whereas extreme compositions for bromide are C 60 Br 6 [1] and C 60 Br 24 [6], and those reported for fluorides are C 60 F 2 and C 60 F 48 [7]. Interestingly, lower chlorides of C 60 and C 70 , C 60 Cl 6 [2] and C 70 Cl 10 [8], differ significantly in their properties such as solubility, stability and reactivity from the corresponding higher chlorides, C 60 Cl 30 [4, 5] and C 70 Cl 28 [9].In the last years, remarkable progress has been achieved in synthesis and investigation of chlorides of higher fullerenes. Using the reaction of fullerenes with a mixture of TiCl 4 and bromine, higher fullerenes D 2 -C 76 (1), three isomers of C 78 (C 2v (2), C 2v (3), and D 3h (5)), and D 2 -C 80 (2) have been selectively chlorinated, respectively, to C 76 Cl 18 [10], C 78 Cl 18 [11, 12], and C 80 Cl 12 [13] in crystalline form thus enabling structural investigation of the connectivity pattern in pristine fullerenes. The chlorinating power of TiCl 4 and Br 2 mixtures depends on the bromine concentration [14, 15], however, on average, it results in the formation of chlorides with lower to middle chlorine content. Higher chlorides can be produced by using stronger chlorinating agents such as Cl 2 or some inorganic chlorides (ICl, SbCl 5 etc.) at higher temperature [16]. For instance, recently chlorination of the mixture of higher fullerenes with SbCl 5 resulted in isolation and structural characterization of C 90 Cl 32 [17]. In this paper, we report the synthesis and single crystal X-ray study of C 78 Cl 30 which seems to be the highest chloride of C 78 fullerene. Experimental SectionC 78 fullerene was separated from toluene extraction of the fullerene soot by a two-step HPLC using a Cosmosil Buckyprep column (10 mm i.d. x 250 mm, Nacalai Tesque Inc.) and toluene as the eluent (5.0 mL min -1 flow rate, 320 nm). Briefly, in the firststep HPLC a mixed fraction comprised of C 76 and two isomers of C 78 was collected, which was subjected to the second-step recycling HPLC separation. After two cycles, the major isomer of C 78 was successfully obtained with the identification and purity confirmed by MALDI-TOF MS analysis. UV-Vis spectrum of the isolated C 78 fullerene dissolved in toluene was recorded on a UVVis-NIR 3600 spectrometer (Shimadzu, Japan).Approximately 0.3 mg of C 78 (2) was placed into a glass ampo...

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Synthesis and Structures of Fullerene Bromides and Chlorides

Cited by 39 publications

References 53 publications

Fusing Pentagons in a Fullerene Cage by Chlorination: IPR D₂‐C₇₆ Rearranges into non‐IPR C₇₆Cl₂₄

Fusing Pentagons in a Fullerene Cage by Chlorination: IPR D₂‐C₇₆ Rearranges into non‐IPR C₇₆Cl₂₄

Geometrical and Electronic Rules in Fullerene‐Based Compounds

Synthesis and Structure of a Highly Chlorinated C₇₈: C₇₈(2)Cl₃₀

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Synthesis and Structures of Fullerene Bromides and Chlorides

Cited by 39 publications

References 53 publications

Fusing Pentagons in a Fullerene Cage by Chlorination: IPR D2‐C76 Rearranges into non‐IPR C76Cl24

Fusing Pentagons in a Fullerene Cage by Chlorination: IPR D2‐C76 Rearranges into non‐IPR C76Cl24

Geometrical and Electronic Rules in Fullerene‐Based Compounds

Synthesis and Structure of a Highly Chlorinated C78: C78(2)Cl30

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Fusing Pentagons in a Fullerene Cage by Chlorination: IPR D₂‐C₇₆ Rearranges into non‐IPR C₇₆Cl₂₄

Fusing Pentagons in a Fullerene Cage by Chlorination: IPR D₂‐C₇₆ Rearranges into non‐IPR C₇₆Cl₂₄

Synthesis and Structure of a Highly Chlorinated C₇₈: C₇₈(2)Cl₃₀