Single-walled carbon nanotube solubilization

Murakami H, Nakamura G, Nomura T, Miyamoto T, Nakashima N (2007) Nanocovalent porphyrin-functionalized single-walled carbon nanotubes solubilization and spectral behaviors. J Porph Phthal 11 418 27... 

R. E. (2001) Reversible water-solubilization of single-walled carbon nanotubes by polymer wrapping. Chem, Phys, Lett, 342, 265-271. 

H. Dodziuk, A. Ejchart, W. Anczewski, H. Ueda, E. Krinichnaya, G. Dolgonos, and W. Kutner, Water solubilization, determination of the number of different types of single-wall carbon nanotubes and their partial separation with respect to diameters by complexation with r/-cyclodextrin, Chem. Commun. (2003) 986-987. 

F. Pompeo and D. E. Resasco, Water solubilization of single-walled carbon nanotubes by functionalization with glucosamine, Nano Lett., 2 (2002) 369-373. 

M.F. Islam, E. Rojas, D.M. Bergey, A.T. Johnson, and A.G. Yodh, High weight fraction surfactant solubilization of single-wall carbon nanotubes in water. Nano Lett. 3, 269-273 (2003). 

Ikeda A, Hayashi K, Konishi T, Kikuchi J (2004) Solubilization and debundling of purified single-walled carbon nanotubes using solubilizing agents in an aqueous solution by high-speed vibration milling technique. Chem. Commun. 1334-1335. 

A. Ghosh, K.V. Rao, R. Voggu, S. J. George, Non-covalent functionalization, solubilization of graphene and single-walled carbon nanotubes with aromatic donor and acceptor molecules, Chemical Physics Letters, vol. 488, pp. 198-201, 2010. 

Fluorous chemistry, involving the use of a fluorous label for the functionalization of a substrate and a fluorous solvent for extraction of the functionalized substrate, is shown to be effective in solubilizing gold and CdSe nanoparticles in a fluorous medium, through phase transfer from an aqueous or a hydrocarbon medium. While these nanoparticles were functionalized with a fluorous thiol, single-walled carbon nanotubes and ZnO nanorods could be solubilized in a fluorous medium by reacting them with a fluorous amine. Fluorous chemistry enables the solubilization of the nanostructures in the most nonpolar liquid medium possible. 

We could solubilize purified single-walled carbon nanotubes (SWNTs)11 in the fluorous medium by reacting them with heptadecafluoroundecylamine. For this purpose, we first prepared SWNTs by the arc discharge method and purified them by HNO3 and FL treatment.11 To solubilize the nanotubes, 1.5 mg of SWNTs, 22 uL of the heptadecafluoroundecylamine (SWNTs/amine = 2 1), and 3 mL of perfluorohexanne were sealed in a 7 mL Teflon-lined stainless steel autoclave and heated at 130 °C for 48 h. This process produced a clear solution of SWNTs in perfluorohexane, as can be seen from Figure 5a. 

In conclusion, we have successfully demonstrated that, by using a fluorous label and a fluorous solvent, we can affect the phase transfer of gold and CdSe nanoparticles from an aqueous or hydrocarbon medium to the fluorous phase. Single-walled carbon nanotubes and ZnO nanorods can be solubilized in a fluorous solvent after interaction with a fluorous amine. Phase transfer of the nanostructures to a fluorous solvent represents solubilization in a highly nonpolar solvent, accompanied by purification. The high nonpolarity of the fluorocarbon makes it possible to study the optical and other properties of nanostructures in a medium of very low refractive index. Since the fluorocarbon extracts only the species attached to the fluorous label, the process enables one to obtain solely one product in the pure state. We believe that fluorous chemistry may have practical utility in carrying out studies of nanostructures. 

O Cormell, M.J., Boul, P., Ericson, L.M., Huffinan, C.B., Wang, Y., Haroz, E., Kuper, C., Tour, J.M., Ausman, K.D., and Smalley, R.E. (2001) Reversible water-solubilization of single-walled carbon nanotubes by polymer wrapping. Chem. Phys. Lett., 342, 265-271. 

Star, A., and Stoddart, J. F., Dispersion and solubilization of single-walled carbon nanotubes with a hyperbranched polymer . Macromolecules, 2002, 35, 7516-7520. 

Qin S, Qin D, Ford W T, Herrera J E, Resasco D E, Bachilo S M and Weisman R B (2004) Solubilization and purification of single-wall carbon nanotubes in water by in situ radical polymerization of sodium 4-styrenesulfonate, Macromolecules 37 3965-3967. 

Bahun, G.J. Wang, C. Adronov, A. (2006). Solubilizing single-walled carbon nanotubes with pyrene-functionaUzed block copolymers. Journal of Polymer Science, Part A Polymer Chemistry, 44,1941-1951. 

Huang, W. Fernando, S. Allard, L.F. Sun, Y.P. (2003). Solubilization of Single-Walled Carbon Nanotubes with Dianrune-Terrriinated Oligomeric Poly(ethylene Glycol) in Different Functionalization Reactions. Nano Letters, 3, 565-568. 

Kahn, M.G.C. Banerjee, S. Wong, S.S. (2002). Solubilization of Oxidized Single-Walled Carbon Nanotubes in Organic and Aqueous Solvents through Organic Derivatization. Nano Letters, 2,1215-1218. 

Single-wall or multi-wall carbon nanotubes have been functionalized with amino-acids, so that these nanomaterials can be solubilized in water and through all the lateral organic chains act as a multidentate ligand [88]. 

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