Stable Dispersions of Fullerenes, C<sub>60</sub> and C<sub>70</sub>, in Water. Preparation and Characterization

Deguchi, Shigeru; Alargova, and Rossitza G.; Tsujii, Kaoru

doi:10.1021/la010651o

Cited by 483 publications

(564 citation statements)

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“…It strongly suggests that the primary mechanism of C 60 fullerene solubilization in water is the attachment of the OH groups to C 60 fullerene carbons, which explains why the lone C 60 molecules and their clusters exist at equilibrium in solution for quite a long time (see above), a feature that is independent of the method of C 60 FAS preparation. It also explains the irreversible character of the adsorption/desorption isotherms reported earlier, 27 the minimal extraction of C 60 fullerene from water−colloid solutions by toluene, 28 and the ability of C 60 fullerenes from C 60 FAS to hold water molecules even in vacuum. 17 The covalent attachment of the OH groups does not exclude the possibility of electron transfer from water molecules to C 60 fullerene, enabling us to explain the negative charge on fullerene particles.…”

Section: ■ Results and Discussionsupporting

confidence: 63%

“…17 The covalent attachment of the OH groups does not exclude the possibility of electron transfer from water molecules to C 60 fullerene, enabling us to explain the negative charge on fullerene particles. 17,18,28 However, the previous model of stabilization of hydrated C 60 fullerene by water molecules joined together by an H-bonding network 17,23 needs to be corrected in view of the available results of molecular dynamics simulations of hydrated C 60 fullerenes 29,30 reporting the weakening and breakage of the H bonds between water molecules in the immediate vicinity of the C 60 fullerene surface as a result of the overbalancing effect of C 60 fullerene−water with respect to the water−water interaction.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

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On the Origin of C₆₀ Fullerene Solubility in Aqueous Solution

et al. 2014

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In this work, we report that the surface hydroxylation of C 60 molecules is the most likely mechanism for pristine C 60 fullerenes/C 60 fullerene aggregate stabilization in water, being independent of the method of C 60 fullerene aqueous solution preparation. ■ INTRODUCTIONNanocarbon materials are used in a wide variety of biomedical applications, including biosensorics, targeted drug delivery, chemotherapy, cellular imaging, and diagnostics. 1 For example, the pristine C 60 fullerenes as a unique class of carbon allotropes are able to penetrate the cell membrane, 2,3 to exhibit antioxidant properties, 4,5 and, being nontoxic (at least at low concentration), 6 to exert specific health effects (e.g., antibacterial, 7 antitumor, 8 and drug carrier 9 ).Biomedical applications require a dispersal of C 60 fullerene in a solvent, with aqueous dispersions being preferred because of biocompatibility, safety, or environmental concerns. Although pristine C 60 fullerenes have extremely low water solubility, they can form stable colloid solutions containing individual C 60 fullerenes as well as C 60 fullerene aggregates (clusters) in water when subjected to extended mixing, sonication, or solvent exchange 10−16 (to be further referred to as a C 60 fullerene aqueous colloid solution (C 60 FAS)). However, the origin of stabilization of such particles in water still remains poorly investigated.At least two approaches have been suggested in order to explain the stability of fullerene particles in water solutions. One of them 17 postulates the formation of a water shell around C 60 molecules stabilized simultaneously by the H-bonding network between the water molecules and charge transfer from water to the C 60 fullerene. Another one 18 suggests that the sonication process induces the covalent attachment of water hydroxyls to C 60 fullerene carbons, resulting in the formation of alcohol moieties that enable C 60 fullerene dissolution. The problem here is that the properties of C 60 FAS (including biological properties) as well as the mechanism of water solubility may depend on the method of preparation of C 60 fullerene aqueous solution. 13,16,17 Indeed, these two approaches differ by the underlying method of C 60 FAS preparation although the sonication step is presented in both methods. The question therefore arises as to whether the mechanism of solubility of C 60 fullerene in water depends on the method of C 60 FAS preparation. This question has been investigated in this article. ■ EXPERIMENTAL SECTIONSample Preparation. For the preparation of C 60 FAS, we used a saturated solution of pure C 60 fullerene (purity >99.99%) in toluene with a C 60 molecule concentration corresponding to maximum solubility near 2.9 mg/mL and the same amount of distilled water in an open beaker. The two phases that formed were treated in an ultrasonic bath. The procedure was continued until the toluene had completely evaporated and the water phase became yellow. Filtration of the aqueous solution allowed us to separate the product from un...

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Section: ■ Results and Discussionsupporting

confidence: 63%

Section: ■ Results and Discussionmentioning

confidence: 99%

On the Origin of C₆₀ Fullerene Solubility in Aqueous Solution

et al. 2014

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“…Previous work by Deguchi et al have shown it possible to create monodisperse clusters of C 60 (60 nm) in water through forced precipitation by addition of a THF-solution into water. [ 12 ] The thought was that a PCBM-analogue, that was not soluble in water, which would allow for subsequent processing, but still containing coordination properties towards aqueous media, might behave in a similar way if mixed with an aqueous solution from THF. The fullerene 2 (see Scheme 1 ) containing an advantages of solubility switching, removal of the side chains from the bulk of the active layer furthermore means removal of non-absorbing material, and several studies show enhanced stability of the active layer towards general degradation.…”

Section: Doi: 101002/aenm201000007mentioning

confidence: 99%

Fabrication of Polymer Solar Cells Using Aqueous Processing for All Layers Including the Metal Back Electrode

Søndergaard

Helgesen

Jørgensen

et al. 2010

Advanced Energy Materials

230

161

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“…The most relevant feature of fullerene C 60 is the ability to act as a free radical scavenger [16]. Properties attributed to the delocalized double bond system of fullerene cage allow C 60 to quench various free radicals more efficiently than conventional antioxidants [10].…”

Section: Introductionmentioning

confidence: 99%

Solubilization of fullerene C60 in micellar solutions of different solubilizers

Torres

Poša

Srdjenović

et al. 2011

Colloids and Surfaces B: Biointerfaces

112

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a b s t r a c tFullerene (C 60 ), the third carbon allotrope, is a classical engineered material with the potential application in biomedicine. However, extremely high hydrophobicity of fullerene hampers its direct biomedical evaluation and application. In this work, we investigated the solubilization of fullerene using 9 different solubility enhancers: Tween 20, Tween 60, Tween 80, Triton X-100, PVP, polyoxyethylene (10) lauryl ether, n-dodecyl trimethylammonium chloride, myristyl trimethylammonium bromide and sodium dodecyl sulphate and evaluated its antioxidant activity in biorelevant media. The presence of C 60 entrapped in surfactant micelles was confirmed by UV/VIS spectrometry. The efficacy of each modifier was evaluated by chemometric analysis using experimental data for investigating the relationship between solubilization and particle size distribution. Hierarchical clustering and principal component analysis was applied and showed that non-ionic surfactants provide better solubilization efficacy (>85%). A correlation was established (r = 0.975) between the degree of solubilization and the surfactant structure. This correlation may be used for prediction of C 60 solubilization with non-tested solubility modifiers. Since the main potential biomedical applications of fullerene are based on its free radical quenching ability, we tested the antioxidant potential of fullerene micellar solutions. Lipid peroxidation tests showed that the micellar solutions of fullerene with Triton and polyoxyethylene lauryl ether kept high radical scavenging activity, comparable to that of aqueous suspension of fullerene and BHT. The results of this work provide a platform for further solubilization and testing of pristine fullerene and its hydrophobic derivatives in a biological benign environment.

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Stable Dispersions of Fullerenes, C₆₀ and C₇₀, in Water. Preparation and Characterization

Cited by 483 publications

References 33 publications

On the Origin of C₆₀ Fullerene Solubility in Aqueous Solution

On the Origin of C₆₀ Fullerene Solubility in Aqueous Solution

Fabrication of Polymer Solar Cells Using Aqueous Processing for All Layers Including the Metal Back Electrode

Solubilization of fullerene C60 in micellar solutions of different solubilizers

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Stable Dispersions of Fullerenes, C60 and C70, in Water. Preparation and Characterization

Cited by 483 publications

References 33 publications

On the Origin of C60 Fullerene Solubility in Aqueous Solution

On the Origin of C60 Fullerene Solubility in Aqueous Solution

Fabrication of Polymer Solar Cells Using Aqueous Processing for All Layers Including the Metal Back Electrode

Solubilization of fullerene C60 in micellar solutions of different solubilizers

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Stable Dispersions of Fullerenes, C₆₀ and C₇₀, in Water. Preparation and Characterization

On the Origin of C₆₀ Fullerene Solubility in Aqueous Solution

On the Origin of C₆₀ Fullerene Solubility in Aqueous Solution