Reaction of [60]fullerene with trialkylphosphine oxide

Wu, Shuisheng; Sun, Wei-Quan; Zhang, Dan‐Wei; Shu, Le; Wu, Hou‐Ming; Xu, Jing-Fei; Lao, Xia-Fei

doi:10.1016/s0040-4039(98)02131-5

Cited by 11 publications

(6 citation statements)

References 6 publications

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“…Among the three phosphines, 2 provided the best results. Unidentifiable impurities were produced at high temperatures via a side reaction in which C 60 reacted with the trialkylphosphine oxide, as previously reported by Wu et al Therefore, the most favorable temperature was found to be 25 °C. Figure shows the purity of C 60 obtained by using 1 at various fullerene concentrations, and it was confirmed that a high concentration (>1.0 wt %) of fullerenes is favorable for the proposed method.…”

Section: Resultssupporting

confidence: 59%

Facile Purification of C₆₀O-Containing [60]Fullerene Using Trialkylphosphines at Room Temperature

Hashiguchi¹,

Nagata²,

Tanaka

2012

Org. Process Res. Dev.

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A novel method using trialkylphosphines is reported for the facile purification of [60]fullerene containing C 60 O. When tri-n-butylphosphine and tri-n-octylphosphine were added to unrefined C 60 (ca. 97% purity) in 1,2,4-trimethylbenzene, C 60 O was readily reduced to give high-purity C 60 (>99% purity). The best results were obtained for a high concentration (>1.0 wt %) of unrefined fullerene treated with tri-n-octylphosphine at room temperature. This method is simple and fast in comparison with conventional alumina chromatography, and thus, it is well-suited to industrial-scale separation.

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Section: Resultssupporting

confidence: 59%

Facile Purification of C₆₀O-Containing [60]Fullerene Using Trialkylphosphines at Room Temperature

Hashiguchi¹,

Nagata²,

Tanaka

2012

Org. Process Res. Dev.

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“…Outros nucleófílos também têm sido adicionados ao C 60 , sendo que dentre eles podem ser citados o cianeto, 48 hidróxidos e alcóxidos, [49][50][51] nucleófilos fosforados, 52 silíl-lítios e germanolítios 53 (Tabela 4).…”

Section: Adição De Outros Nucleófilosunclassified

Fulereno[C60]: química e aplicações

Santos¹,

Rocha²,

Alves³

et al. 2010

Quím. Nova

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Recebido em 7/5/09; aceito em 22/9/09; publicado na web em 25/2/10 FULLERENE C 60 : CHEMISTRY AND APPLICATIONS. Fullerene chemistry has become a very active research field in the two last decades, largely because of the exceptional properties of the C 60 molecule and the variety of fullerene derivatives that appear to be possible. In this review, a general analysis of fullerene C 60 reactivity is performed. The principal methods for the covalent modification of this fascinating carbon cage are presented. The prospects of using fullerene derivatives as medicinal drugs and photoactive materials in light converting devices are demonstrated.Keywords: fullerene C 60 ; nanomaterials; carbon allotropes. Este artigo de revisão teve o objetivo de sistematizar as principais informações relacionadas à reatividade singular desta forma de carbono e aos principais métodos até então desenvolvidos para a funcionalização química do fulereno [C 60 ] bem como exemplificar a grande e versátil gama de aplicações encontradas até hoje para esta nanomolécula e seus derivados quimicamente modificados. INTRODUÇÃO HISTÓRICO, MÉTODOS DE OBTENÇÃO E PURIFICAÇÃOEmbora desde 1966 cálculos teóricos demonstrassem a possibilidade da existência de "gaiolas" estáveis formadas exclusivamente por átomos de carbono, 2 somente em 1985 um experimento realizado por Kroto et al. comprovou experimentalmente a existência de tais compostos. 3 Nesse experimento, uma placa de grafite foi submetida a um laser pulsado de alta frequência e os agregados gerados no plasma foram analisados por espectrometria de massas. O experimento mostrou a formação de moléculas grandes constituídas exclusivamente por átomos de carbono, com fórmula C n onde n= 30-190, sendo C 60 e C 70 os mais abundantes. Sob condições específicas para a formação destes agregados, o espectro de massas apresentou o pico do C 60 como principal. Esta molécula, excepcionalmente estável e simétrica, foi chamada pelos pesquisadores de fullerene em homenagem ao arquiteto americano B. Fuller, responsável pela invenção dos domos geodési-cos, forma arquitetônica que segue o mesmo princípio de simetria e estabilidade. Sir H. W. Kroto, R. F. Curl e R. E. Smalley procuravam, neste experimento, mimetizar condições interestelares para comprovar a existência de grandes e excepcionais cadeias de carbono no espaço e não suspeitavam que, graças a sua descoberta, seriam agraciados com o Nobel de Química alguns anos mais tarde, em 1996.A descoberta destas espécies moleculares de carbono excitou profundamente a comunidade científica. Entretanto, somente em 1990, R. Taylor, um especialista em cromatografia, foi capaz de obter pela primeira vez 4 amostras puras de C 60 e C 70 em quantidades mínimas, mas suficiente para começar a exploração de suas propriedades químicas e espectroscópicas. No mesmo ano, o desenvolvimento por Krätschmer et al. 5 de um método para a síntese de C 60 em quantidades "macroscópicas" representou uma etapa decisiva para a área que se tornou, nos últimos 20 anos, um tema maior da química contempo...

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“…Among the myriad of fullerene derivatives reported today, only a limited number of fullerene compounds containing a phosphorus atom are known . Scarce examples of phosphorylated fullerene derivatives with the phosphorus atom attached directly to the fullerene skeleton have been reported and are limited to hydrofullerenes only. , Wu et al explored the reaction of C 60 with trialkylphosphine oxides and obtained hydrofullerenes R 2 (O)PC 60 H . Nakamura and co-workers described the reaction of C 60 with a lithiated phosphine–borane or a lithiated phosphinite borane followed by acid quenching and removal of the BH 3 group to afford a phosphine or a phosphinite bearing a fullerene substituent.…”

Section: Introductionmentioning

confidence: 99%

Radical Reaction of [60]Fullerene with Phosphorus Compounds Mediated by Manganese(III) Acetate

Wang

Zou

2011

J. Org. Chem.

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Radical reaction of [60]fullerene with phosphonates or phosphine oxide mediated by manganese(III) acetate dihydrate in chlorobenzene under three different conditions afforded three different types of phosphorylated fullerenes: singly bonded fullerene dimers 2, hydrophosphorylated fullerenes 3, and acetoxylated fullerene derivatives 4. In addition, interconversions among the three types of phosphorylated fullerene derivatives have also been investigated. A possible reaction mechanism was proposed to explain experimental results.

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Reaction of [60]fullerene with trialkylphosphine oxide

Cited by 11 publications

References 6 publications

Facile Purification of C₆₀O-Containing [60]Fullerene Using Trialkylphosphines at Room Temperature

Facile Purification of C₆₀O-Containing [60]Fullerene Using Trialkylphosphines at Room Temperature

Fulereno[C60]: química e aplicações

Radical Reaction of [60]Fullerene with Phosphorus Compounds Mediated by Manganese(III) Acetate

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Reaction of [60]fullerene with trialkylphosphine oxide

Cited by 11 publications

References 6 publications

Facile Purification of C60O-Containing [60]Fullerene Using Trialkylphosphines at Room Temperature

Facile Purification of C60O-Containing [60]Fullerene Using Trialkylphosphines at Room Temperature

Fulereno[C60]: química e aplicações

Radical Reaction of [60]Fullerene with Phosphorus Compounds Mediated by Manganese(III) Acetate

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Facile Purification of C₆₀O-Containing [60]Fullerene Using Trialkylphosphines at Room Temperature

Facile Purification of C₆₀O-Containing [60]Fullerene Using Trialkylphosphines at Room Temperature