The Higher Fullerenes: Isolation and Characterization of C
 76
 , C
 84
 , C
 90
 , C
 94
 , and C
 70
 O, an Oxide of D
 5h
 -C
 70

Diederich, François; Ettl, Roland; Rubin, Yves; Whetten, Robert L.; Beck, Rainer; Alvarez, Marcos M.; Anz, Samir J.; Sensharma, Dilip K.; Wudl, Fred; Khemani, K. C.; Koch, Andreas

doi:10.1126/science.252.5005.548

Cited by 657 publications

(226 citation statements)

References 24 publications

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“…The presence of large metal atoms within the cage leads to differing reactivities and properties which can be exploited for numerous applications, including those in the biomedical realm. 46 In that 7 Bingel reaction mechanism. Deprotonation by the strong base gives the nucleophilic malonate anion which then attacks the [6,6] bond.…”

Section: Endohedral Metallofullerenesmentioning

confidence: 99%

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: Endohedral Metallofullerenesmentioning

confidence: 99%

Water-soluble fullerenes for medical applications

Rašović

2017

Materials Science and Technology

118

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“…³ÖÜÇÔÕÄÇÐÐÑ, ÚÕÑ ÏÑAEÇ-ÎËÓÑÄÂÐËÇ ÏÇÕÑAEÑÏ ÏÑÎÇÍÖÎâÓÐÑÌ AEËÐÂÏËÍË ÒÑÍÂÊÞ-ÄÂÇÕ, ÚÕÑ ÅÑÓâÚËÇ ÖÅÎÇÓÑAEÐÞÇ ÍÎÂÔÕÇÓÞ, ÐÂÚËÐÂâ Ô n 30, AEÂÉÇ ÒÓË ÕÇÏÒÇÓÂÕÖÓÇ 3000 ¬ ÖÉÇ ËÏÇáÕ ÕÓÇØ-ÏÇÓÐÖá ÔÕÓÖÍÕÖÓÖ Ô ÊÂÏÍÐÖÕÑÌ ÒÑÄÇÓØÐÑÔÕßá [55] ±ÓÇAEÒÑÎÂÅÂÎÑÔß, ÚÕÑ ÏÂÎÞÇ ×ÖÎÎÇÓÇÐÞ ÏÑÅÖÕ ÑÃÓÂ-ÊÑÄÞÄÂÕßÔâ Ä ÓÇÊÖÎßÕÂÕÇ ÏÐÑÅÑÍÓÂÕÐÑÌ ÄÔÕÂÄÍË ÏËÍÓÑ-ÍÎÂÔÕÇÓÑÄ C 2 Ä ÔÕÓÖÍÕÖÓÖ ÕÓÇØÏÇÓÐÞØ ÒÑÎËÙËÍÎËÚÇÔÍËØ ÖÅÎÇÓÑAEÐÞØ ÍÎÂÔÕÇÓÑÄ [59]. ³ÑÅÎÂÔÐÑ ÐÇÍÑÕÑÓÞÏ ÓÂÔÚÇ-ÕÂÏ ×ÖÎÎÇÓÇÐ ËÏÇÇÕ ÏÂÍÔËÏÂÎßÐÖá àÐÇÓÅËá ÔÄâÊË ÔÓÇAEË ËÊÑÏÇÓÑÄ ÍÎÂÔÕÇÓÂ C 20 (ÔÏ., ÐÂÒÓËÏÇÓ, [44,60,61] [88], C 44 [9], C 50 [9,88] Ë C 76 [88] ÒÓË ÃÞÔÕÓÑÏ ÑØÎÂÉAEÇÐËË Ä ÔÄÇÓØÊÄÖÍÑÄÑÌ ÔÕÓÖÇ ØÑÎÑAEÐÑÅÑ ÃÖ×ÇÓÐÑÅÑ ÅÂÊÂ; 5) C 44 Ë C 50 Ä ÄÇÓØÐÇÌ ÚÂÔÕË ÒÎÂÏÇÐË [20]; 6) C 76 ÔÓÇAEË ÒÓÑAEÖÍÕÑÄ ×ÑÕÑÓÂÔÒÂAEÂ ×ÖÎÎÇÓÇÐÑÄ C 94 [89], C 36 [90], C 44 , C 50 [90,91] ÔÓÇAEË ÒÓÑAEÖÍÕÑÄ ×ÑÕÑÓÂÔÒÂAEÂ ×ÖÎÎÇÓÇÐÂ C 60 ; 7) C 36 , C 44 Ë C 50 ÒÓË ÒÑÎÖÚÇÐËË ×ÖÎÎÇÓÇÐÑÄ Ä ØËÏËÚÇÔÍÑÏ ÓÇÂÍÕÑÓÇ, ÔÑAEÇÓÉÂÜÇÏ ÔÏÇÔß C 2 H 2 Ë SF 6 [18]. £ ÐÇÍÑÕÑÓÞØ ÖÔÎÑÄËâØ ÏÂÔÔ-ÔÒÇÍÕÓ ÐÇ ÔÑAEÇÓÉËÕ ÏÂÅËÚÇÔÍËØ ×ÖÎÎÇÓÇÐÑÄ, ÐÂÒÓË-ÏÇÓ ÒÓË ÂÃÎâÙËË ÖÅÎÇÓÑAEÔÑAEÇÓÉÂÜËØ ÏÂÕÇÓËÂÎÑÄ Ä ÄÂÍÖÖÏ [9,11,12] ËÎË Ä ÔÄÇÓØÊÄÖÍÑÄÖá ÔÕÓÖá [28,34,88].…”

Section: ³ãñóíâ ëê íîâôõçóñäunclassified

Formation and growth of carbon nanostructures: fullerenes, nanoparticles, nanotubes and cones

Lozovik¹,

Popov²

1997

Usp. Fiz. Nauk

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“…The initial reactant for production of the fullerenes is, apparently, the carbon atom (and possibly C 2 ), and the smallest stable fullerenes that, at this writing (September 1991), have been isolated are C^ and C 7Q (7). Thus, the number of unstable chemical intermediates potentially involved in carbon-arc fullerene synthesis is huge, and it includes all the structural isomers of the bare carbon clusters C 2 through C^9, excluding C^.…”

Section: The Chemical Modelmentioning

confidence: 99%

Synthesis of C₆₀ from Small Carbon Clusters

Heath

1992

ACS Symposium Series

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A model based on experiment and ab initio theory for the high-yield carbon--arc synthesis of C 60 and other fullerenes is presented. Evidence that is given indicates that the synthesis must start with the smallest units of carbon (atoms, dimers, etc.). The model is then broken into four steps: (1) the growth of carbon chains up to length C 10 from initial reactants present in the carbon vapor, (2) growth from chains into monocyclic rings (C 10 -C 20 ), (3) production and growth of three-dimensional reactive carbon networks (C 21 -C x , x = 30-40), and (4) growth of small fullerene cages via a closed--shell mechanism that exclusively produces C 60 , C 70 , and the higher fullerenes as the stable products.The carbon-arc synthesis of from solid graphite surely represents one of the most phenomenal phase transitions ever discovered. This synthetic technique, developed by Kratschmer, Fostiropoulos, and Huffman (7), has made bulk quantities of and other fullerenes available to the scientific community. This availability has stimulated a tremendous effort directed at characterizing this novel and exciting new class of molecules. One of the most fascinating aspects of the fullerenes, however, is the chemistry of their formation within the carbon arc. The synthesis is amazingly simple, and yet it produces results that are so fantastic and unexpected! The best experimental evidence (more on this later) indicates that the graphite reactant is vaporized in the carbon arc into the smallest units of carbon-atoms and possibly dimers-which then, through a concerted series of reactions, and in a limited range of pressures and temperatures, recombine to produce the spheroidal shells of carbon known as the fullerenes (2).How can this reaction scheme be understood? What are the individual chemical mechanisms that lead to the formation of the fullerenes? What reactive intermediates are produced in the carbon arc? How does the hightemperature chemical environment of the carbon arc produce the low-entropy

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The Higher Fullerenes: Isolation and Characterization of C ₇₆ , C ₈₄ , C ₉₀ , C ₉₄ , and C ₇₀ O, an Oxide of D _5h -C ₇₀

Cited by 657 publications

References 24 publications

Water-soluble fullerenes for medical applications

Water-soluble fullerenes for medical applications

Formation and growth of carbon nanostructures: fullerenes, nanoparticles, nanotubes and cones

Synthesis of C₆₀ from Small Carbon Clusters

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The Higher Fullerenes: Isolation and Characterization of C 76 , C 84 , C 90 , C 94 , and C 70 O, an Oxide of D 5h -C 70

Cited by 657 publications

References 24 publications

Water-soluble fullerenes for medical applications

Water-soluble fullerenes for medical applications

Formation and growth of carbon nanostructures: fullerenes, nanoparticles, nanotubes and cones

Synthesis of C60 from Small Carbon Clusters

Contact Info

Product

Resources

About

The Higher Fullerenes: Isolation and Characterization of C ₇₆ , C ₈₄ , C ₉₀ , C ₉₄ , and C ₇₀ O, an Oxide of D _5h -C ₇₀

Synthesis of C₆₀ from Small Carbon Clusters