C<sub>72</sub>Cl<sub>4</sub>: A Pristine Fullerene with Favorable Pentagon-Adjacent Structure

Tan, Yuan‐Zhi; Zhou, Ting; Bao, Jian; Shan, Gui-Juan; Xie, Su‐Yuan; Huang, Rong‐Bin; Zheng, Lan‐Sun

doi:10.1021/ja108860y

Cited by 52 publications

(69 citation statements)

References 21 publications

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“…Therefore, analogous to #11188 C 72 Cl 4 and other non-IPR chlorofullerenes, there are four Cl atoms placed at the fused pentagons through one [5,5] bond in a zigzag manner. 15,16 Further chlorination on C 74 Cl 4 was investigated. The fifth addition takes place again in the carbon atom with the highest HOMO contribution (see Figure 3d), and the sixth addition is to the position with the highest spin density in C 74 Cl 5 ( Figure 3e).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Capturing the Fused-Pentagon C₇₄ by Stepwise Chlorination

et al. 2016

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As a bridge to connect medium-sized fullerenes, fused-pentagon C74 is still missing heretofore. Of 14 246 possible isomers, the first fused-pentagon C74 with the Fowler-Manolopoulos code of 14 049 was stabilized as C74Cl10 in the chlorine-involving carbon arc. The structure of C74Cl10 was identified by X-ray crystallography. The stabilization of pristine fused-pentagon C74 by stepwise chlorination was clarified in both theoretical simulation with density functional theory calculations and experimental fragmentation with multistage mass spectrometry.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Capturing the Fused-Pentagon C₇₄ by Stepwise Chlorination

et al. 2016

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“…Experimental results have recently reported, for the first time, the higher stability of a non-IPR fullerene compared to its related IPR isomer for C 72 Cl 4 [279,280] (Fig. 35).…”

Section: Fullerenes For Molecular Wiresmentioning

confidence: 94%

Buckyballs

Delgado

Filippone

Giacalone

et al. 2013

Topics in Current Chemistry

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Buckyballs represent a new and fascinating molecular allotropic form of carbon that has received a lot of attention by the chemical community during the last two decades. The unabating interest on this singular family of highly strained carbon spheres has allowed the establishing of the fundamental chemical reactivity of these carbon cages and, therefore, a huge variety of fullerene derivatives involving [60] and [70]fullerenes, higher fullerenes, and endohedral fullerenes have been prepared. Much less is known, however, of the chemistry of the uncommon non-IPR fullerenes which currently represent a scientific curiosity and which could pave the way to a range of new fullerenes. In this review on buckyballs we have mainly focused on the most recent and novel covalent chemistry of fullerenes involving metal catalysis and asymmetric synthesis, as well as on some of the most significant advances in supramolecular chemistry, namely H-bonded fullerene assemblies and the search for efficient concave receptors for the convex surface of fullerenes. Furthermore, we have also described the recent advances in the macromolecular chemistry of fullerenes, that is, those polymer molecules endowed with fullerenes which have been classified according to their chemical structures. This review is completed with the study of endohedral fullerenes, a new family of fullerenes in which the carbon cage of the fullerene contains a metal, molecule, or metal complex in the inner cavity. The presence of these species affords new fullerenes with completely different properties and chemical reactivity, thus opening a new avenue in which a more precise control of the photophysical and redox properties of fullerenes is possible. The use of fullerenes for organic electronics, namely in photovoltaic applications and molecular wires, complements the study and highlights the interest in these carbon allotropes for realistic practical applications. We have pointed out the so-called non-IPR fullerenes - those that do not follow the isolated pentagon rule - as the most intriguing class of fullerenes which, up to now, have only shown the tip of the huge iceberg behind the examples reported in the literature. The number of possible non-IPR carbon cages is almost infinite and the near future will show us whether they will become a reality.

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“…According to the X‐ray crystal structure of #11188 C 72 Cl 4 , the non‐IPR #11188 C 72 cage has one pair of DFPs, with two chlorine atoms bonded to the junction of the fused pentagons (Figure a), thereby releasing the unfavorable local strain. The two additional chlorine atoms are bonded at two pentagon‐hexagon‐hexagon vertexes, thus satisfying the “local‐aromaticity” principle . In the same year, Jansen and co‐workers synthesized the same C 2 v ‐ #11,188 C 72 Cl 4 compound by using the high‐frequency furnace technique with CCl 4 as a chlorinating agent .…”

Section: Stabilization Of Double Fused Pentagons (Dfps)mentioning

confidence: 99%

Strain Release of Fused Pentagons in Fullerene Cages by Chemical Functionalization

et al. 2019

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According to the isolated pentagon rule (IPR), for stable fullerenes, the 12 pentagons should be isolated from one another by hexagons, otherwise the fused pentagons will result in an increase in the local steric strain of the fullerene cage. However, the successful isolation of more than 100 endohedral and exohedral fullerenes containing fused pentagons over the past 20 years has shown that strain release of fused pentagons in fullerene cages is feasible. Herein, we present a general overview on fused‐pentagon‐containing (i.e. non‐IPR) fullerenes through an exhaustive review of all the types of fused‐pentagon‐containing fullerenes reported to date. We clarify how the strain of fused pentagons can be released in different manners, and provide an in‐depth understanding of the role of fused pentagons in the stability, electronic properties, and chemical reactivity of fullerene cages.

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C₇₂Cl₄: A Pristine Fullerene with Favorable Pentagon-Adjacent Structure

Cited by 52 publications

References 21 publications

Capturing the Fused-Pentagon C₇₄ by Stepwise Chlorination

Capturing the Fused-Pentagon C₇₄ by Stepwise Chlorination

Buckyballs

Strain Release of Fused Pentagons in Fullerene Cages by Chemical Functionalization

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C72Cl4: A Pristine Fullerene with Favorable Pentagon-Adjacent Structure

Cited by 52 publications

References 21 publications

Capturing the Fused-Pentagon C74 by Stepwise Chlorination

Capturing the Fused-Pentagon C74 by Stepwise Chlorination

Buckyballs

Strain Release of Fused Pentagons in Fullerene Cages by Chemical Functionalization

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C₇₂Cl₄: A Pristine Fullerene with Favorable Pentagon-Adjacent Structure

Capturing the Fused-Pentagon C₇₄ by Stepwise Chlorination

Capturing the Fused-Pentagon C₇₄ by Stepwise Chlorination