Nucleophilic-alkylation-reoxidation: A functionalization sequence for single-wall carbon nanotubes

Graupner R, Abraham J, Wunderlich D, Vencelová A, Lauffer P, Röhrl J, Hundhausen M, Ley L, Hirsch A (2006)

Publication Type: Journal article, Original article

Publication year: 2006


Original Authors: Graupner R., Abraham J., Wunderlich D., Vencelova A., Lauffer P., Röhrl J., Hundhausen M., Ley L., Hirsch A.

Publisher: American Chemical Society

Book Volume: 128

Pages Range: 6683-6689

Journal Issue: 20

DOI: 10.1021/ja0607281


A new reaction sequence for the chemical functionalization of single-wall carbon nanotubes (SWNTs) consisting of the nucleophilic addition of t-BuLi to the sidewalls of the tubes and the subsequent reoxidation of the intermediates t-BuSWNT leading to t-BuSWNT was developed. During the formation of the t-BuSWNT, a homogeneous dispersion in benzene was formed due to the electrostatic repulsion of the negatively charged intermediates causing debundling. The entire reaction sequence can be repeated, and the degree of functionalization of the products (t-Bu)SWNT (m = 1-3) increases with increasing m. Degrees of functionalization expressed as the carbon-to-addend ratio of up to 31 were reached. The reaction was studied in detail by photoelectron spectroscopy, Raman spectroscopy, and scanning tunneling microscopy (STM). The C 1s core level spectra reveal that the nucleophilic attack of the t-BuLi leads to negatively charged SWNTs. Upon oxidation, this negative charge is removed. The valence band spectra of the functionalized samples exhibit a significant reduction in the π-derived density of states. In STM, the covalently bonded t-butyl groups attached to the sidewalls have been visualized. Raman spectroscopy reveals that addition of the nucleophile to metallic tubes is preferred over the addition to semiconducting tubes. © 2006 American Chemical Society.

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Graupner, R., Abraham, J., Wunderlich, D., Vencelová, A., Lauffer, P., Röhrl, J.,... Hirsch, A. (2006). Nucleophilic-alkylation-reoxidation: A functionalization sequence for single-wall carbon nanotubes. Journal of the American Chemical Society, 128(20), 6683-6689.


Graupner, Ralf, et al. "Nucleophilic-alkylation-reoxidation: A functionalization sequence for single-wall carbon nanotubes." Journal of the American Chemical Society 128.20 (2006): 6683-6689.

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