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Issue 13, 2008
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Preferred functionalization of metallic and small-diameter single walled carbon nanotubesvia reductive alkylation

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Abstract

A selectivity investigation of the covalent sidewall functionalization of SWNTs by reductive alkylation (Billups reaction) is reported. The functionalized tubes Rn-SWNT were characterized by UV-vis-nIR absorption, nIR emission and Raman spectroscopy. The reduction of SWNTs with sodium and the subsequent alkylation of the reduced tubes SWNTn with butyl iodide reveal a pronounced SWCNT diameter dependence, that is, SWNTs with smaller diameter are considerably more reactive than tubes with larger diameter. Moreover, this reaction sequence also favours the preferred functionalization of metallic over semiconducting tubes. Treatment of the reduced intermediates SWNTn with protons, via the use of ethanol, instead of alkyl iodide leads to hydrogenated tubes. However, in this case the degree of functionalization is considerably lower than that observed for the corresponding alkylation. Also no pronounced preference of the reaction of metallic and small diameter tubes was observed during the hydrogenation process.

Graphical abstract: Preferred functionalization of metallic and small-diameter single walled carbon nanotubesvia reductive alkylation

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Publication details

The article was received on 30 Oct 2007, accepted on 06 Dec 2007 and first published on 04 Jan 2008


Article type: Paper
DOI: 10.1039/B716732F
Citation: J. Mater. Chem., 2008,18, 1493-1497
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    Preferred functionalization of metallic and small-diameter single walled carbon nanotubesvia reductive alkylation

    D. Wunderlich, F. Hauke and A. Hirsch, J. Mater. Chem., 2008, 18, 1493
    DOI: 10.1039/B716732F

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