Volume 2008, Issue 15 p. 2544-2550
Full Paper

Covalent Sidewall Functionalization of SWNTs by Nucleophilic Addition of Lithium Amides

Zois Syrgiannis

Zois Syrgiannis

Department of Chemistry and Pharmacy and Central Institute of Advanced Materials and Processes (ZMP), University of Erlangen-Nürnberg, 91054 Erlangen, Germany, Fax: + 49-9131-8526864

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Frank Hauke

Frank Hauke

Department of Chemistry and Pharmacy and Central Institute of Advanced Materials and Processes (ZMP), University of Erlangen-Nürnberg, 91054 Erlangen, Germany, Fax: + 49-9131-8526864

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Jonas Röhrl

Jonas Röhrl

Technische Physik, University of Erlangen-Nürnberg, 91058 Erlangen, Germany

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Martin Hundhausen

Martin Hundhausen

Technische Physik, University of Erlangen-Nürnberg, 91058 Erlangen, Germany

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Ralf Graupner

Ralf Graupner

Technische Physik, University of Erlangen-Nürnberg, 91058 Erlangen, Germany

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Yiannis Elemes

Yiannis Elemes

Department of Chemistry, University of Ioannina, Dourouti, 45110 Ioannina, Greece

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Andreas Hirsch

Andreas Hirsch

Department of Chemistry and Pharmacy and Central Institute of Advanced Materials and Processes (ZMP), University of Erlangen-Nürnberg, 91054 Erlangen, Germany, Fax: + 49-9131-8526864

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First published: 05 May 2008
Citations: 92

Graphical Abstract

The synthesis and characterization of sidewall amino-functionalized single-walled carbon nanotube derivatives (nPrNH)n-SWNTs is reported. The nucleophilic addition of in situ generated lithium n-propylamide to the sidewall of SWNTs and the subsequent reoxidation of charged intermediates of the type (nPrNH)n-SWNTn– leads to carbon nanotube derivatives with covalently attached amino groups.

Abstract

The synthesis and characterization of sidewall-functionalized SWNT derivatives (nPrNH)n-SWNTs containing n-propylamine addends is reported. The nucleophilic addition of in situ generated lithium n-propylamide to the sidewall of SWNTs and the subsequent reoxidation of charged intermediates of the type (nPrNH)n-SWNTn leads to carbon nanotube derivatives with covalently attached amino groups. Based on the reaction sequence, a homogeneous dispersion of the carbon nanotube material is achieved as a result of the electrostatic repulsion of negatively charged intermediates. The solubility of the resulting propylamine-functionalized (nPrNH)n-SWNT material in organic solvents is drastically increased. The functionalized tubes were characterized in detail by Raman spectroscopy, thermogravimetric analysis (TGA/MS), X-ray photoelectron spectroscopy (XPS) and UV/Vis/NIR spectroscopy. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)