Wraparound Hosts for Fullerenes: Tailored Macrocycles and Cages

Canevet, David; Pérez, Emilio M.; Martín, Nazario

doi:10.1002/anie.201101297

Cited by 223 publications

(139 citation statements)

References 98 publications

(104 reference statements)

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“…On the other hand, the use cages assembled by metals have been proved to be an interesting strategy for the encapsulation of fullerenes. Some recent reviews of host/guest systems for fullerene has been published [289,290], below the most recent developments are discussed. several metal complexes able to host fullerenes and functionalized fullerenes (Fig.…”

Section: Supportmentioning

confidence: 99%

Coordination chemistry on carbon surfaces

Axet¹,

Dechy‐Cabaret²,

Durand³

et al. 2016

Coordination Chemistry Reviews

110

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Section: Supportmentioning

confidence: 99%

Coordination chemistry on carbon surfaces

Axet¹,

Dechy‐Cabaret²,

Durand³

et al. 2016

Coordination Chemistry Reviews

110

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“…Any application, however, is limited in origin by tedious solidliquid extractions (usually in toluene) and time-expensive chromatographic separations [6][7][8][9][10][11][12][13][14][15] . More recently, the host-guest chemistry of molecular containers has been explored to encapsulate fullerenes 16 . Still selectivity is usually difficult to achieve because fine modulation of the size of molecular cages to accommodate different fullerenes is challenging with the limitations of covalent synthesis 17 .…”

mentioning

confidence: 99%

Sponge-like molecular cage for purification of fullerenes

et al. 2014

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Since fullerenes are available in macroscopic quantities from fullerene soot, large efforts have been geared toward designing efficient strategies to obtain highly pure fullerenes, which can be subsequently applied in multiple research fields. Here we present a supramolecular nanocage synthesized by metal-directed self-assembly, which encapsulates fullerenes of different sizes. Direct experimental evidence is provided for the 1:1 encapsulation of C 60 , C 70 , C 76 , C 78 and C 84 , and solid state structures for the host-guest adducts with C 60 and C 70 have been obtained using X-ray synchrotron radiation. Furthermore, we design a washingbased strategy to exclusively extract pure C 60 from a solid sample of cage charged with a mixture of fullerenes. These results showcase an attractive methodology to selectively extract C 60 from fullerene mixtures, providing a platform to design tuned cages for selective extraction of higher fullerenes. The solid-phase fullerene encapsulation and liberation represent a twist in host-guest chemistry for molecular nanocage structures.

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“…21 Structure of the switchable receptor 51 and scheme showing its switching between the "off" and "on" states and its binding to C 60 Fig. 20 Chemical structure of the biscalix [5]arene host 49 [157], the "jaws" receptor 50 [158], and X-ray crystal structure of the 50·C 60 complex actually be detrimental to the binding event [166]. We will now see a few examples of macrocyclic hosts for fullerenes to illustrate these points.…”

Section: Tweezers and Macrocycles For The Molecular Recognition Of Fumentioning

confidence: 95%

“…There are many other examples of tweezer-like and macrocyclic hosts for fullerenes, which we will not discuss in this chapter. The interested reader can refer to more comprehensive reviews [144,166]. In this very brief account we intended to outline general considerations regarding the design principles for the construction of hosts for fullerenes, illustrating them with a few selected examples.…”

Section: Tweezers and Macrocycles For The Molecular Recognition Of Fumentioning

confidence: 99%

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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Wraparound Hosts for Fullerenes: Tailored Macrocycles and Cages

Cited by 223 publications

References 98 publications

Coordination chemistry on carbon surfaces

Coordination chemistry on carbon surfaces

Sponge-like molecular cage for purification of fullerenes

Buckyballs

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