Chemical Attachment of Organic Functional Groups to Single-walled Carbon Nanotube Material
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Chemical attachment of organic functional groups to single-walled carbon nanotube material Y. Chen and R. C. Haddon Departments of Chemistry and Physics, University of Kentucky, Lexington, Kentucky 40506-0055
S. Fang, A. M. Rao, and P. C. Eklund Department of Physics and Astronomy, University of Kentucky, Lexington, Kentucky 40506-0055
W. H. Lee, E. C. Dickey, and E. A. Grulke Department of Chemical and Materials Engineering, University of Kentucky, Lexington, Kentucky 40506-0055
J. C. Pendergrass, A. Chavan, and B. E. Haley Departments of Chemistry and Pharmacy, University of Kentucky, Lexington, Kentucky 40506-0055
R. E. Smalley Center for Nanoscale Science and Technology, Rice Quantum Institute and Departments of Chemistry and Physics, Rice University, Houston, Texas 77251 (Received 6 February 1998; accepted 3 May 1998)
We have subjected single-walled carbon nanotube materials (SWNTM’s) to a variety of organic functionalization reactions. These reactions include radioactive photolabeling studies using diradical and nitrene sources, and treatment with dichlorocarbene and Birch reduction conditions. All of the reactions provide evidence for chemical attachment to the SWNTM’s, but because of the impure nature of the staring materials, we are unable to ascertain the site of reaction. In the case of dichlorocarbene we are able to show the presence of chlorine in the SWNT bundles, but as a result of the large amount of amorphous carbon that is attached to the tube walls, we cannot distinguish between attachment of dichlorocarbene to the walls of the SWNT’s and reaction with the amorphous carbon.
I. INTRODUCTION
While present single-walled nanotube (SWNT) studies are focused on the as-prepared, pristine, and doped materials,1–3 if the SWNT’s are to achieve their full potential, it will be necessary to bring about chemical modification of the basic structure. The ability to disperse and perhaps dissolve the SWNT’s would greatly improve the prospects for processible materials that can be aligned and formed into useful structures. Chemical functionalization would be an important step in this direction as well as opening up interesting opportunities in its own right. If it were possible to chemically modify the surface of the nanotube in a controlled manner, this would afford a number of opportunities for tailoring the structural and electronic properties. It is important to distinguish the functionalization that is proposed here from the type of chemistry that is usually carried out on graphite. For example, it is well known that under sufficiently forcing conditions, graphite will undergo fluorination and oxidation processes that lead to almost completely saturated structures. In this way, most of the interesting electronic properties of graphite are lost. What is required here, is a reagent J. Mater. Res., Vol. 13, No. 9, Sep 1998
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that will selectively attack a few of the p-bonds in a controlled manner without br
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