Complexation of Carbon Nanorings with Fullerenes: Supramolecular Dynamics and Structural Tuning for a Fullerene Sensor

Kawase, Takeshi; Tanaka, Kenji; Seirai, Yohko; Shiono, Nami; Oda, Masaji

doi:10.1002/ange.200352033

Cited by 44 publications

(18 citation statements)

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“…In order to increase the depth of the cavity, and in turn increase interactions between host and fullerene, macrocycles 42-44 ( Fig. 18) were synthesized [147]. In these carbon nanorings at least two of the p-phenylene moieties are substituted by naphthalene units.…”

Section: On Concave-convex Interactionsmentioning

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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Section: On Concave-convex Interactionsmentioning

confidence: 99%

Buckyballs

Delgado

Filippone

Giacalone

et al. 2013

Topics in Current Chemistry

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“…They subsequently studied the molecular recognition of roughly 1 · 10 5 and 1 · 10 6 dm 3 mol À1 and Stern-Völmer constants K SV of 2.6 · 10 5 and 4.3 · 10 6 dm 3 mol À1 , respectively. Using competitive complexation experiments, the selectivity of 78 for C 70 vs. C 60 was determined to be >10:1 [75]. Multicomponent onion-type complexes were then prepared, with two SPMs encompassing a single fullerene molecule, such as 77 ' 76 ' C 60 and 71 ' 68 ' C 60 (Scheme 6.18B) [76].…”

Section: Spms In Host-guest Systemsmentioning

confidence: 99%

“…A 4:1 mixture of 72/74 gave the corresponding mixture of SPMs 68 and 70, which could be separated by GPC, while pure samples of 73 and 75 could be obtained to provide 69 and 71 directly[73,74]. Using the same bromination/dehydrobromination procedure, SPMs 76-78 were synthesized with 1,4-or 2,6-naphthylene units, respectively, at opposing positions (Scheme 6.18B).SPMs 68 and 76 have a diameter of 1.31 nm, which is suitable for inclusion of C 60 , while that of 78 (1.41 nm) is nearly perfect for inclusion of C 70[75] 3). The 78 ' C 60 and 78 ' C 70 complexes are extremely stable, with association constants K a of Examples of Diederichs saccharide receptors 62-66[71,72] and disaccharide receptor 67[69,70] based on R-binaphthol.…”

mentioning

confidence: 99%

“…Scheme 6.18 (A) Synthesis of paraphenylacetylene SPMs 68-71through bromination/dehydrobromination[74] and (B) molecular structure of SPMs 76-78[75] and onion complex 77 ' 76 ' C 60[76].yield of SPM 80 was marginally higher under Hay (13%) than Breslow conditions (9%). SPM 80 acted as a fluorescence-quenching sensor for Cu(II) and Ag(I), while 81 functioned as a sensor only for Cu(II)[79].…”

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confidence: 99%

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Shape‐Persistent Macrocycles Based on Acetylenic Scaffolding

Sadowy

Tykwinski

2008

Modern Supramolecular Chemistry

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“…Oda and his group very recently prepared the acid-and oxygen-sensitive PAMs 167 and 168, which can be stored in dilute solution at 0 hC over a month [60]. These macrocycles were shown to associate with both C 60 and C 70 and to form extremely stable complexes.…”

Section: Para-pamsmentioning

confidence: 99%