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Synlett 2004(1): 155-160  
DOI: 10.1055/s-2003-44983
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© Georg Thieme Verlag Stuttgart · New York

Diazonium-Based Functionalization of Carbon Nanotubes: XPS and GC-MS Analysis and Mechanistic Implications

Christopher A. Dyke, Michael P. Stewart, Francisco Maya, James M. Tour*
Departments of Chemistry and Mechanical Engineering and Materials Science, and Center for Nanoscale Science and Technology, MS 222, Rice University, 6100 Main Street, Houston, Texas 77005, USA
Fax: +1(713)3486250; e-Mail: tour@rice.edu;
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Publication History

Received 29 September 2003
Publication Date:
08 December 2003 (online)

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Abstract

A reaction product analysis of single wall carbon nanotubes functionalized by solvent-free and aqueous-based arenedia­zonium species is discussed. Both GC-MS on the thermolysis products along with XPS analysis of the materials, suggests that the only functionality on the SWNT is the arene group. The mechanism is indicative of either direct aryl radical addition to the SWNT or (a) electron injection from the nanotube to the arenediazonium species, (b) reaction of the SWNT-radical cation with an aryl radical, followed by (c) an electron transfer to the nanotube. A method for ­defunctionalizing the nanotubes is disclosed wherein the SWNTs are resuspendable in organic solvent.

Key words

nanotube functionalization - fullerene - defunctionalization - aryl radical - carbon nanotubes