Survey of Chemical Reactivity of C<sub>60</sub>, Electrophile and Dieno—polarophile Par Excellence

Wudl, Fred; Hirsch, Andreas; Khemani, K. C.; Suzuki, Toshishige M.; Allemand, P. M.; Koch, Andreas; Eckert, H.; Srdanov, G.; Webb, Hugh M.

doi:10.1021/bk-1992-0481.ch011

Cited by 168 publications

(98 citation statements)

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“…19,20 Amination One of the first reactions to be carried out with fullerenes was the direct amination of C 60 . 21 Wudl et al simply mixed C 60 in a series of neat aliphatic primary amines (n-propylamine, t-butylamine 7 and dodecylamine) for 16-24 h, observing a colour change through blue/green to brown. Precise elucidation of the number of adducts in each reaction was not carried out, although an average of six adducts was calculated 8 for the n-propylamine reaction.…”

Section: Exohedral Functionalisationmentioning

confidence: 99%

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Water-soluble fullerenes for medical applications

Rašović

2017

Materials Science and Technology

118

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Research on fullerenes occupies a unique position in the scientific arena. Synthesis and characterisation of this nanomaterial blur the line between materials science and chemistry; careful tuning of the processing methods gives birth to a whole family of molecules and their functionalised derivatives, whose unusual properties at this nanoscopic scale can be exploited in cutting-edge technological applications. This review focuses on the functionalisation of fullerenes for use in medical applications. The first half gives an introduction to the fullerenes themselves and how their fundamental properties lead to a very rich chemistry, enabling both exohedral (external) and endohedral (internal) functionalisations of the cage. Emphasis is placed on the need for safe and reproducible synthesis routes if fullerenes are ever going to make it to the pharmaceutical market. In line with this, a selection of exohedral functionalisation protocols receives particular attention. Coverage of endohedral fullerene synthesis routes is limited to the endohedral metallofullerenes. In the second half, myriad applications of fullerenes in biomedical contexts are introduced and certain synthesis routes are critically evaluated. Discussion of the need to water solubilise the hydrophobic fullerene cages precedes an overview of fullerene-based diagnostic and therapeutic technologies. A final moment is spent on toxicity studies of fullerenes. The concluding remarks emphasise the positive effects of incorporating fullerenes into biomedical technologies, while looking at how these are perceived by the general public. A case is made for fullerenes being the optimal choice as standard bearers in the advance of nanomaterials into the medical field. This is the winning review of the 2016 Materials Literature Review Prize of the Institute of Materials, Minerals and Mining, run by the Editorial Board of MST. Sponsorship of the prize by TWI Ltd is gratefully acknowledged.

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Section: Exohedral Functionalisationmentioning

confidence: 99%

“…22 Amination is an important reaction as it can lead to water-soluble derivatives, as demonstrated by the reaction of C 60 with ethylenediamine. 21 The reaction mechanism for amination of C 60 is described in Fig. 4; addition occurs across the [6,6] bond.…”

Section: Exohedral Functionalisationmentioning

confidence: 99%

Water-soluble fullerenes for medical applications

Rašović

2017

Materials Science and Technology

118

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“…[161][162][163]431,432 Simple monoaddition is rare. The reaction typically continues until six amines have been added, presumably via the same mechanism.…”

Section: Fullerides As Intermediatesmentioning

confidence: 99%

Discrete Fulleride Anions and Fullerenium Cations

2000

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His research interests include reactive cation and superacid chemistry with inert carborane counterions, ionic liquids, bioinorganic chemistry, spin-coupling phenomena, fullerene chemistry, and new carbon-or porphyrin-based materials. He is a Sloan Fellow, a Dreyfus Teacher−Scholar Awardee, and a Guggenheim Fellow. Robert Bolskar received his B.S. degree in Chemistry from Carroll College in Waukesha, WI, in 1992. He earned his Ph.D. degree at the University of Southern California in Los Angeles under the direction of Christopher Reed in 1997, investigating the synthetic redox chemistry of fullerene anions and cations. In 1998 he moved to the University of California, Riverside, as Managing Research Associate. He is currently Senior Chemist at TDA Research in Wheat Ridge, CO. His research interests include the chemistry and physics of fullerene compounds, supramolecular chemistry, strongly oxidizing systems, and electrophilic cations.

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“…Wudl and co-workers [37,38] showed that 1,3-dipoles are particularly well suited for reactions with C 60 , but it was later shown by several other groups [39±42] that 1,3-dienes (such as cyclopentadiene) [43,44] also react very well. The cycloaddition is reversible, [45] but the addition product can be isolated and characterized.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Optical-Limiting Behavior of Hybrid Inorganic-Organic Materials from the Sol-Gel Processing of Organofullerenes

Maggini¹,

Faveri²,

Scorrano³

et al. 1999

Chem. Eur. J.

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The optical-limiting properties of a series of novel [60]fullerene derivatives have been investigated in toluene solutions and in sol ± gel glasses. Working at different wavelengths, it is found that the efficiency of the new compounds compares well with that of pristine C 60 . In particular, better performance of the organofullerenes is obtained when the pumping wavelength approaches the triplet ± triplet absorption maximum of the derivatives at % 700 nm. The main component in the optical-limiting behavior is, in fact, ascribed to a reverse saturable absorption mechanism. A relevant feature in the structure of the new organofullerenes is that a silicon-alkoxide moiety is covalently attached to C 60 . This guarantees the grafting of the fullerene spheroid to the silicon matrix during the sol ± gel process. Some of the derivatives show remarkable solubility in THF, a solvent widely used in sol ± gel processing, in which C 60 is itself insoluble.

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Survey of Chemical Reactivity of C₆₀, Electrophile and Dieno—polarophile Par Excellence

Cited by 168 publications

References 0 publications

Water-soluble fullerenes for medical applications

Water-soluble fullerenes for medical applications

Discrete Fulleride Anions and Fullerenium Cations

Synthesis and Optical-Limiting Behavior of Hybrid Inorganic-Organic Materials from the Sol-Gel Processing of Organofullerenes

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Survey of Chemical Reactivity of C60, Electrophile and Dieno—polarophile Par Excellence

Cited by 168 publications

References 0 publications

Water-soluble fullerenes for medical applications

Water-soluble fullerenes for medical applications

Discrete Fulleride Anions and Fullerenium Cations

Synthesis and Optical-Limiting Behavior of Hybrid Inorganic-Organic Materials from the Sol-Gel Processing of Organofullerenes

Contact Info

Product

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Survey of Chemical Reactivity of C₆₀, Electrophile and Dieno—polarophile Par Excellence