An Entrant of Smaller Fullerene: C<sub>56</sub> Captured by Chlorines and Aligned in Linear Chains

Tan, Yuan‐Zhi; Han, Xiaopeng; Wu, Xin; Meng, Ye-Yong; Zhu, Feng; Zhuo-zhen, Qian; Liao, Z.; Chen, Ming‐Hui; Lü, Xin; Xie, Su‐Yuan; Huang, Rong‐Bin; Zheng, Lan‐Sun

doi:10.1021/ja806352v

Cited by 68 publications

(52 citation statements)

References 29 publications

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“…It is known that the open-circuit voltage (V oc ) of a fullerene-based organic solar cell depends heavily on the HOMO level of the polymer donor and the LUMO level of the fullerene acceptor. As a useful electron-acceptor material, the fullerene derivative of 1-(3-methoxycarbonyl) propyl-1-phenylA C H T U N G T R E N N U N G [6,6] C 61 (PC 60 BM) has been employed widely in P3HT:PC n BM bulk heterojunction solar cells. [28] However, the LUMO of PC 60 BM is too low to prepare a P3HT:PC 60 BM bulk heterojunction solar cell with higher V oc .…”

Section: Wwwchemeurjorgmentioning

confidence: 99%

Combustion Synthesis and Electrochemical Properties of the Small Hydrofullerene C₅₀H₁₀

Chen

Gao

Weng

et al. 2012

Chemistry A European J

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The hydrofullerene C(50)H(10) is synthesized by low-pressure benzene-oxygen diffusion combustion. The structure of C(50)H(10) is identified through NMR, mass spectrometry, and IR and Raman spectroscopy as a D(5h) symmetric closed-cage molecule with five pairs of fused pentagons stabilized by ten hydrogen atoms. UV/Vis and fluorescence spectrometric analyses disclose its optical properties as comparable with those of its chloride cousin (C(50)Cl(10)). Cyclic and square-wave voltammograms reveal that the first reduction potential of C(50)H(10) is more negative than that of C(50)Cl(10) as well as C(60), with implications for the utilization of C(50)H(10) as a promising electron acceptor for photovoltaic applications.

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Section: Wwwchemeurjorgmentioning

confidence: 99%

Combustion Synthesis and Electrochemical Properties of the Small Hydrofullerene C₅₀H₁₀

Chen

Gao

Weng

et al. 2012

Chemistry A European J

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“…And compared to the IPR-satisfying C 60 , many hydrides and fluorides of IPR-violating C 60 [16,17] were calculated to be more energetically stable. Besides, experimental investigations have also suggested that C 20 H 20 [18], C 50 Cl 10 [19], and C 56 Cl 10 [20] were energetically stable. For non-IPR fullerene derivatives, both theoretical and experimental investigations reported previously revealed that it was necessary to saturate all the active sites (the carbons atoms shared by two or three pentagons) [19,21,22].…”

Section: Introductionmentioning

confidence: 99%

A theoretical investigation on the structures and stabilities of C60X18 and C70X10 (X = H, F, Cl, and Br)

Gao

Gan

et al. 2011

Struct Chem

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A density functional theory study was performed on fullerene derivatives C 60 X 18 and C 70 X 10 (X = H, F, Cl, and Br). The calculated results show that the lowest energy isomers are IPR-satisfying for C 60 X 18 (X = H, F, Cl, and Br). It is found that the addition patterns of X (X = Cl and Br) are different from those of X (X = H and F) for C 60 , demonstrating that the stability of fullerene derivatives is partly attributed to the steric repulsion and electronegativity of added atoms. However, the lowest energy isomers are IPR-violating for C 70 X 10 (X = H, F, and Cl), suggesting that many more fullerene derivatives may violate the isolated pentagon rule.

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“…[35] Recently, it has been demonstrated that in situ chlorination during classical fullerene synthesis offers valuable opportunities by effectively capturing various intermediates, thereby allowing for their isolation and structural characterization. Thus, besides a plethora of new interesting fullerenes species, [36][37][38][39][40][41][42] numerous perchlorinated polycyclic aromatic hydrocarbons (PAHs) have been identified by utilizing this process. [43][44][45][46][47][48] The spectrum of isolated products served as the first experimental support for the pentagon road (PR) model of fullerene formation.…”

Section: Introductionmentioning

confidence: 99%

Perchloropyracylene and its Fusion with C₆₀ by Chlorine‐Assisted Radio‐Frequency Furnace Synthesis

Mueller

Ziegler

Amsharov

et al. 2011

Chemistry A European J

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Elusive perchloropyracylene has been obtained during conventional fullerene synthesis in a chlorine-containing atmosphere by using the radio-frequency furnace technique. In contrast to its hydrocarbon analogue, the title compound was found to be unexpectedly stable. Although the high stability of perchloropyracylene impedes its direct addition to C(60) fullerene, the corresponding adduct was found in the synthesis products extracted from the raw soot. Both new species were separated and unambiguously characterized by single-crystal X-ray analysis. According to experimental observations and quantum chemical calculations, the addition of perchloropyracylene to the C(60) fullerene can only be realized by involving highly reactive species such as C(14) clusters displaying the pyracylene connectivity. Such a viable mechanism includes capturing of free or partially chlorinated C(14) clusters with pyracylene-type connectivity by the fullerene molecule and subsequent stabilization through chlorine addition. The data obtained provide experimental evidence for the presence of pyracylene-like C(14) clusters in the gas phase, which have evolved during the graphite vaporization process. According to the pentagon road mechanism, such clusters are regarded as crucial intermediates in fullerene formation.

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An Entrant of Smaller Fullerene: C₅₆ Captured by Chlorines and Aligned in Linear Chains

Cited by 68 publications

References 29 publications

Combustion Synthesis and Electrochemical Properties of the Small Hydrofullerene C₅₀H₁₀

Combustion Synthesis and Electrochemical Properties of the Small Hydrofullerene C₅₀H₁₀

A theoretical investigation on the structures and stabilities of C60X18 and C70X10 (X = H, F, Cl, and Br)

Perchloropyracylene and its Fusion with C₆₀ by Chlorine‐Assisted Radio‐Frequency Furnace Synthesis

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An Entrant of Smaller Fullerene: C56 Captured by Chlorines and Aligned in Linear Chains

Cited by 68 publications

References 29 publications

Combustion Synthesis and Electrochemical Properties of the Small Hydrofullerene C50H10

Combustion Synthesis and Electrochemical Properties of the Small Hydrofullerene C50H10

A theoretical investigation on the structures and stabilities of C60X18 and C70X10 (X = H, F, Cl, and Br)

Perchloropyracylene and its Fusion with C60 by Chlorine‐Assisted Radio‐Frequency Furnace Synthesis

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Product

Resources

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An Entrant of Smaller Fullerene: C₅₆ Captured by Chlorines and Aligned in Linear Chains

Combustion Synthesis and Electrochemical Properties of the Small Hydrofullerene C₅₀H₁₀

Combustion Synthesis and Electrochemical Properties of the Small Hydrofullerene C₅₀H₁₀

Perchloropyracylene and its Fusion with C₆₀ by Chlorine‐Assisted Radio‐Frequency Furnace Synthesis