Synthesis and properties of novel fullerene derivatives having dendrimer units and the fullerenyl anions generated therefrom

Murata, Yasujiro; Ito, M.; Komatsu, Kôichi

doi:10.1039/b201334g

Cited by 39 publications

(19 citation statements)

References 50 publications

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“…432 nm), along with its tail, hinders confirmative analysis. [77] Nevertheless, in the region above 450 nm of the spectrum, distinctively enhanced absorption tails are observed in a consistent pattern for fullerene-OPE hybrids 28-31. These absorption bands differ from the UV/Vis patterns obtained by simply summing the UV/Vis curves of pristine fullerene and respective OPE oligomers (see Supporting Information).…”

Section: Electronic Absorption Propertiesmentioning

confidence: 57%

“…There is a substantial red- (Table 1) of 1 H and 13 C NMR resonances for compound 30 based on long-range proton-carbon couplings, 2D NMR experiments, and calculated 13 C shifts for C 60 H(CCH). [77] The assignments for C5, C6, and C7 are tentative. shift of the l max value by about 10 nm from compounds 32 to 33, which is comparable to the shift observed in the spectra of their OPE precursors 14 and 16.…”

Section: Electronic Absorption Propertiesmentioning

confidence: 98%

“…Initially, we followed the ethynylation procedure as described in the literature, [38,[74][75][76][77] in which lithium acetylides were first generated by nBuLi or tBuLi and then transferred into a slurry of fullerene in THF under an inert atmosphere. However, this method was found to work only for the ethynylation of mono-terminal alkynes with fullerene, whereas the fullerene addition to multiple terminal alkyne species failed to yield the desired multiple fullerenealkyne adducts.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, Spectroscopic and Nonlinear Optical Properties of Multiple [60]Fullerene–Oligo(p‐phenylene ethynylene) Hybrids

Zhao

Shirai

Slepkov

et al. 2005

Chemistry A European J

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A series of multiple [60]fullerene terminated oligo(p-phenylene ethynylene) (OPE) hybrid compounds has been synthesized through a newly developed in situ ethynylation method. Structural and magnetic shielding properties of the highly unsaturated carbon-rich C(60) and OPE scaffolds were characterized by 1D and 2D NMR spectroscopic analyses. Electronic interactions between the [60]fullerenes and the OPE backbones were investigated by UV/Vis spectroscopic and cyclic voltammetry (CV) experiments. Our studies clearly show that although the multiple [60]fullerene groups are connected via pi-conjugated OPE frameworks, they present diminutive electronic interactions in the ground state, and the electronic behavior of the [60]fullerene cages are only affected by the OPE backbones through modest inductive effects. Interestingly, sizable third-order nonlinear optical (NLO) responses (gamma) and enhanced two-photon absorption (TPA) cross-sections (sigma((2))) were determined for the multifullerene-OPE hybrid 31 relative to its OPE precursor from differential optical Kerr effect (DOKE) experiments. Such enhanced NLO performance is presumably due to the occurrence of periconjugation and/or charge transfer effects in the excited state. In addition, comparatively strong excited-state absorption was observed and characterized for OPE pentamer 12. Thus, the use of such fullerene-derivatized conjugated oligomers aids the quest for molecules with large third-order NLO and TPA properties.

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Section: Electronic Absorption Propertiesmentioning

confidence: 57%

Section: Electronic Absorption Propertiesmentioning

confidence: 98%

Section: Introductionmentioning

confidence: 99%

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Synthesis, Spectroscopic and Nonlinear Optical Properties of Multiple [60]Fullerene–Oligo(p‐phenylene ethynylene) Hybrids

Zhao

Shirai

Slepkov

et al. 2005

Chemistry A European J

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“…43 para a formação do correspondente ânion RC 60 -como intermediário da reação, que pode ser protonado ou alquilado. 44 Estas adições podem ser realizadas pela geração in situ do organometálico 45,46 ou diretamente pela adição de um reagente organometálico comercial. A Tabela 3 apresenta alguns exemplos destas adições ao C 60 .…”

Section: Esquema 3 Ciclopropanação Do C 60unclassified

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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“…Recently Ito, Komatsu, and co-workers have used this approach to investigate a series of fullerodendrimers (9)(10)(11) in which Fréchet-type dendrons have been connected to a fullerene moiety via an acetylene linker (Fig. 5) [35]. Both energy and electron transfer quenchers have been employed to show that the quenching rates of the fullerene triplet state are decreased as a function of the size of the dendrimer shell [36].…”

Section: A Fullerene Core To Probe Dendritic Shielding Effectsmentioning

confidence: 99%

Fullerodendrimers: Fullerene-Containing Macromolecules with Intriguing Properties

Nierengarten

2003

Topics in Current Chemistry

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Fullerenes possess electronic and photophysical properties which make them natural candidates for the preparation of functional dendrimers. The attachment of a controlled number of dendrons on a C(60) core provides a compact insulating layer around the carbon sphere, and the triplet lifetimes of the C(60) chromophore can be used to evaluate its degree of isolation from external contacts. The fullerene core can also act as a terminal energy receptor in dendrimer-based light-harvesting systems. When a fullerodendrimer is further functionalized with a suitable electron donor, it may exhibit the essential features of a multicomponent artificial photosynthetic system in which photo-induced energy transfer from the antenna to the C(60) core is followed by electron transfer. On the other hand, the preparation of dendrons with peripheral C(60) subunits or containing a C(60) sphere at each branching unit has been achieved. These fullerodendrons are not only interesting building blocks for the synthesis of monodisperse fullerene-rich macromolecules with intriguing properties, but they are also amphiphilic compounds capable of forming stable Langmuir films at the air-water interface.

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Synthesis and properties of novel fullerene derivatives having dendrimer units and the fullerenyl anions generated therefrom

Cited by 39 publications

References 50 publications

Synthesis, Spectroscopic and Nonlinear Optical Properties of Multiple [60]Fullerene–Oligo(p‐phenylene ethynylene) Hybrids

Synthesis, Spectroscopic and Nonlinear Optical Properties of Multiple [60]Fullerene–Oligo(p‐phenylene ethynylene) Hybrids

Fulereno[C60]: química e aplicações

Fullerodendrimers: Fullerene-Containing Macromolecules with Intriguing Properties

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