Embracing C<sub>60</sub> with Multiarmed Geodesic Partners

Mizyed, Shehadeh; Georghiou, Paris E.; Bancu, Mihail; Cuadra, Bernardo; Amarjit, K.; Cheng, Pei‐Chao; Scott, Lawrence T.

doi:10.1021/ja016761z

Cited by 177 publications

(142 citation statements)

References 17 publications

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“…They act as a fullerene receptor. The K a values of 38 and 39 for C 60 is $300 M À1 and $1400 M À1 in toluene, respectively [67,68]. A double concave hydrocarbon Buckycatcher 40 composed of two corannulene moieties prepared by Sygula includes a C 60 molecule in the concave cavity in the solid and solution state (K a ¼ 8600 M À1 ) (Figure 3.17) [69].…”

Section: Receptors Based On Bowl-shaped Conjugated Systemsmentioning

confidence: 99%

Receptors for Pristine Fullerenes Based on Concave–Convex π–πInteractions

Kawase

2012

Supramolecular Chemistry of Fullerenes and Carbon Nanotubes

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In 1990, Kr€ atchmer and coworkers reported the extraction of fullerenes (C 60 and C 70 ) from carbon soot using aromatic solvents (Figure 3.1) [1]. After this discovery, receptor molecules for fullerenes have been extensively studied for separation and purification of fullerenes. Supramlecular chemists have found that traditional host molecules composed of electron-rich aromatic rings such as calix[n]arenes 1-4, oxacalix[3]arenes 5, and cyclotriveratrylenes (CTV) 6 ( Figure 3.2) can be employed for the purpose. The crystallographic analyses of these complexes with C 60 clearly indicated the importance of the p-p interactions between the convex p surface of C 60 and the concave p surface of the traditional host molecules. On the other hand, except a few examples, the traditional hosts bound fullerenes only in solid state. In order to bind with fullerenes more tightly, two strategies have been presented to construct the well preorganized p cavity so far. First, electron-rich aromatic units are introduced to the host molecule as appendants (Figure 3.2a). Second, two host molecules are linked by appropriate tether(s) to form a dimeric structure with a creft-, ring-, or ball-shaped cavity (Figure 3.2b). The binding abilities of the modified receptors fairly increased in comparison with those of simple traditional hosts. On the other hand, new receptors based on curved conjugated systems such as corannulene 7, extended TTF (exTTF) 8, and carbon nanorings (Figure 3.3) have been developed recently. These compounds possess a concave p surface matching to the convex surface of C 60 . Cyclic [6]paraphenyleneacetylene ([6]CPPA) 9 and the related compounds have smooth belt-shaped structure similar to a cut piece of carbon nanotube, and thus may be termed carbon nanorings. These receptors form stable inclusion complexes with fullerenes both in solution and in the solid state, and are good model compounds to explore the nature of the concave-convex p-p interactions. This chapter discusses the fullerene receptors bearing a cavity surrounded by p-orbitals, the so-called p cavity, the concept of molecular designs, and the nature of p-p interactions. The survey of the fullerene receptors should provide an insight into the supramolecular properties of curved conjugated systems. Although the receptor Supramolecular Chemistry of Fullerenes and Carbon Nanotubes, First Edition. Edited by Nazario Martin and Jean-Francois Nierengarten.

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Section: Receptors Based On Bowl-shaped Conjugated Systemsmentioning

confidence: 99%

Receptors for Pristine Fullerenes Based on Concave–Convex π–πInteractions

Kawase

2012

Supramolecular Chemistry of Fullerenes and Carbon Nanotubes

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“…Even the presence of C 70 can affect the nature of the host-guest complex of C 60 with a host molecule. [23] Figure 1 summarises the main types of "host" molecules that have been used for the for- mation of complexes of C 60 and includes cavitands 1-4, 7 [21] and 9, [22] saddle-shaped molecules 5, porphyrins 6, siloxanes 8, curved-faced tryptophanes 10, [23] and β-and γ-cyclodextrins (n = 7, 8) 11, although not all of these lead to crystalline material and structure authentication by using diffraction data. When complexation is not prevalent, the addition of other synthons can be effective.…”

Section: Introductionmentioning

confidence: 99%

Structural Diversity of Host–Guest and Intercalation Complexesof Fullerene C₆₀

et al. 2006

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Pristine fullerene C60 has a fcc structure. Crystallisation of the fullerene in a variety of solvents can lead to inclusion complexes, as well as discrete host–guest complexes in the presence of cavitands and porphyrins, and related molecules. The complexes retain varying degrees of fullerene···fullerene interactions at the van der Waals limit, except in a limited number of cases where the fullerenes are completely shrouded by one or more included/host molecule. Analysis of the fullerene···fullerene interactions in these complexes reveals a diverse structural arrangement of the fullerenes. They can be organised into dimers, single linear columns or zigzag chains, double columns, spectacular fivefold Z‐shaped columnar arrays, hexagonal close‐packed layers, corrugated sheets, honeycomb motifs, non‐close‐packed layers and complex three‐dimensional networks. Disorder of the fullerenes in the solid state is common, although structures with close‐packed planar arrangements of C60 molecules and/or with symmetry matching between the host molecule and the fullerene (two‐, three‐ and fivefold symmetry) tend to have less disorder of the fullerene. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

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“…Direct nucleophilic substitution of 46 with nucleophiles makes it possible to produce 48. The treatment of 46 with sodium arylthiolates gave 1,3,5,7,9-pentakis(arylthio)corannulene derivatives 48 (XR¼SAr) [83,91] the reaction of 46 with various sodium alkoxides required high temperature (180 C) [83]. The reaction mechanism should be via a Meisenheimer complex [92] rather than an aryne intermediate.…”

Section: Synthesismentioning

confidence: 99%

Synthesis, Structures, and Physical Properties of Aromatic Molecular-Bowl Hydrocarbons

Siegel

2014

Topics in Current Chemistry

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This chapter summarizes the synthesis, physical properties, structure, and crystal packing of buckybowls. Buckybowls exemplify an intermediate class of polynuclear aromatic compounds between the closed-shell fullerenes and the flat extended arrays of graphene. These warped sheets can be seen as fragments of fullerenes or the end cap of single-walled carbon nanotubes; and, their curvature endows them with physical properties distinct from flat polynuclear hydrocarbons, which opens up unique possibilities for molecular bowls in various organic materials applications.

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Embracing C₆₀ with Multiarmed Geodesic Partners

Cited by 177 publications

References 17 publications

Receptors for Pristine Fullerenes Based on Concave–Convex π–πInteractions

Receptors for Pristine Fullerenes Based on Concave–Convex π–πInteractions

Structural Diversity of Host–Guest and Intercalation Complexesof Fullerene C₆₀

Synthesis, Structures, and Physical Properties of Aromatic Molecular-Bowl Hydrocarbons

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Embracing C60 with Multiarmed Geodesic Partners

Cited by 177 publications

References 17 publications

Receptors for Pristine Fullerenes Based on Concave–Convex π–πInteractions

Receptors for Pristine Fullerenes Based on Concave–Convex π–πInteractions

Structural Diversity of Host–Guest and Intercalation Complexesof Fullerene C60

Synthesis, Structures, and Physical Properties of Aromatic Molecular-Bowl Hydrocarbons

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Product

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Embracing C₆₀ with Multiarmed Geodesic Partners

Structural Diversity of Host–Guest and Intercalation Complexesof Fullerene C₆₀