Synthesis and Structural Characterization of C<sub>70</sub>H<sub>38</sub>

Wågberg, Thomas; Hedenström, Mattias; Talyzin, Alexandr V.; Sethson, Ingmar; Tsybin, Yury O.; Purcell, Jeremiah M.; Marshall, Alan G.; Noréus, Dag; Johnels, Dan

doi:10.1002/anie.200705450

Cited by 16 publications

(6 citation statements)

References 35 publications

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“…Due to the effect of the addends, the topology of the derivatized cage may differ from that of the most stable pristine cage . Conversely, in moderate-temperature conditions (typically from room temperature to 500 °C), as in solution chlorination, solid/gas hydrogenation, , solid-phase fluorination, solid/liquid bromination, or gas phase ion–molecule reactions, fullerene cages are already formed before the addition and their topology usually remains unaltered during the reaction. Occasionally exceptions are found, where the fullerene cage may undergo Stone–Wales skeletal rearrangement or C 2 loss − or insertion. , The final products may be kinetically controlled and correspond to local minima of the potential energy surface.…”

Section: Introductionmentioning

confidence: 99%

Topology-Based Approach to Predict Relative Stabilities of Charged and Functionalized Fullerenes

Wang

Díaz‐Tendero

Alcamı́

et al. 2018

J. Chem. Theory Comput.

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Understanding the relationship between structure and stability is one of the fundamental aspects of fullerene chemistry, as the number of possible cage isomers is very large and complexity increases by orders of magnitude when chemical groups are attached to the fullerene cage. The well-established stability rules valid for neutral fullerenes do not apply to many charged or functionalized fullerenes. Here we present the theory, implementation, and applications of two simple topology-based models that allow one to predict the relative stability of charged and functionalized fullerenes without the need for quantum chemistry calculations: (i) the charge stabilization index (CSI) model, based on the concepts of cage connectivity and frontier π orbitals, which offers a general framework for the relative stability of both positively and negatively charged fullerenes, as well as endohedral metallofullerenes, and (ii) the exohedral fullerene stabilization index (XSI) model, which incorporates all key factors governing the stability of exohedral fullerenes, namely, π delocalization, σ strain, and steric hindrance between addends. Based exclusively on topological information, both models are powerful prescreening tools for predicting the most stable structures of a large number of charged and functionalized fullerenes. For easy use by fullerene chemists, both models have been implemented in the FullFun (for Fullerene Functionalization) software package, whose effectiveness and efficiency are demonstrated by some illustrative examples.

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Section: Introductionmentioning

confidence: 99%

Topology-Based Approach to Predict Relative Stabilities of Charged and Functionalized Fullerenes

Wang

Díaz‐Tendero

Alcamı́

et al. 2018

J. Chem. Theory Comput.

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“…In the lab, prototype exohedral fullerenes are produced by arc-discharges, combustion, , or radio frequencies. , These are high-temperature methods in which fullerene cages are formed through carbon-clustering processes (bottom-up growth), so that the resulting products usually correspond to the global energy minimum of the potential energy surface. Alternatively, they can also be synthesized in solution from existing pristine fullerene cages, as in hydrogenation, , halogenation, , and cycloaddition reactions. − These are low-temperature methods that usually preserve the original structure of the fullerene cage, so that the resulting products correspond to local minima of the potential energy surface.…”

Section: Introductionmentioning

confidence: 99%

Relative Stability of Empty Exohedral Fullerenes: π Delocalization versus Strain and Steric Hindrance

et al. 2017

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Predicting and understanding the relative stability of exohedral fullerenes is an important aspect of fullerene chemistry, since the experimentally formed structures do not generally follow the rules that govern addition reactions or the making of pristine fullerenes. First-principles theoretical calculations are of limited applicability due to the large number of possible isomeric forms, for example, more than 50 billion for CX. Here we propose a simple model, exclusively based on topological arguments, that allows one to predict the relative stability of exohedral fullerenes without the need for electronic structure calculations or geometry optimizations. The model incorporates the effects of π delocalization, cage strain, and steric hindrance. We show that the subtle interplay between these three factors is responsible for (i) the formation of non-IPR (isolated pentagon rule) exohedral fullerenes in contrast with their pristine fullerene counterparts, (ii) the appearance of more pentagon-pentagon adjacencies than predicted by the PAPR (pentagon-adjacency penalty rule), (iii) the changes in regioisomer stability due to the chemical nature of the addends, and (iv) the variations in fullerene cage stability with the progressive addition of chemical species.

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“…[1][2][3][4][5][6][7] Usually, hydrogenated carbon materials are synthesized by treating the carbon precursors under a H 2 atmosphere at high pressure and high temperatures or by plasma-enhanced chemical vapor deposition (PE-CVD) which produces hydrogenated amorphous carbon. [11][12][13] Other processes have also been developed to produce hydrogenated carbon materials. [14][15][16] For instance, Maier et al synthesized hydrogen-containing hierarchically mesoporous carbon using a complex template-based process.…”

Section: Introductionmentioning

confidence: 99%

“…Wågberg et al synthesized hydrogenated carbon nanostructures by treating fullerenes and fullerene filled carbon nanotubes at high pressure and high temperatures under a H 2 atmosphere. 11 Chen et al prepared hydrogenated graphene via a synchronized reduction and hydrogenation of graphene oxide in an aqueous suspension under 60 Co gamma ray irradiation at room temperature. 16 The electrochemical properties of such modified carbon materials can give a significantly enhanced performance when used as anode materials for lithium-ion batteries (LIBs).…”

Section: Introductionmentioning

confidence: 99%

The effect of hydrogenation on the growth of carbon nanospheres and their performance as anode materials for rechargeable lithium-ion batteries

et al. 2015

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Hydrogenated carbon nanomaterials exhibit many advantages in both mechanical and electrochemical properties, and thus have a wide range of potential applications. However, methods to control the hydrogenation and the effect of hydrogenation on the microstructure and properties of the produced nanomaterials have rarely been studied. Here we report the synthesis of hydrogenated carbon nanospheres (HCNSs) with different degrees of hydrogenation by a facile solvothermal method, in which C2H3Cl3/C2H4Cl2 was used as the carbon precursor and potassium as the reductant. The hydrogenation level of the obtained nanospheres depends on the reaction temperature and higher temperature leads to lower hydrogenation due to the fact that the breaking of C-H bonds requires more external energy. The reaction temperature also affects the diameter of the HCNSs and larger spheres are produced at higher temperatures. More importantly, the size and the degree of hydrogenation are both critical factors for determining the electrochemical properties of the HCNSs. The nanospheres synthesized at 100 °C have a smaller size and a higher hydrogenation degree and show a capacity of 821 mA h g(-1) after 50 cycles, which is significantly higher than that of the HCNSs produced at 150 °C (450 mA h g(-1)). Our study opens a possible way for obtaining high-performance anode materials for rechargeable lithium-ion batteries.

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Synthesis and Structural Characterization of C₇₀H₃₈

Cited by 16 publications

References 35 publications

Topology-Based Approach to Predict Relative Stabilities of Charged and Functionalized Fullerenes

Topology-Based Approach to Predict Relative Stabilities of Charged and Functionalized Fullerenes

Relative Stability of Empty Exohedral Fullerenes: π Delocalization versus Strain and Steric Hindrance

The effect of hydrogenation on the growth of carbon nanospheres and their performance as anode materials for rechargeable lithium-ion batteries

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Synthesis and Structural Characterization of C70H38

Cited by 16 publications

References 35 publications

Topology-Based Approach to Predict Relative Stabilities of Charged and Functionalized Fullerenes

Topology-Based Approach to Predict Relative Stabilities of Charged and Functionalized Fullerenes

Relative Stability of Empty Exohedral Fullerenes: π Delocalization versus Strain and Steric Hindrance

The effect of hydrogenation on the growth of carbon nanospheres and their performance as anode materials for rechargeable lithium-ion batteries

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Synthesis and Structural Characterization of C₇₀H₃₈