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Issue 3, 2019
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Reductive diazotation of carbon nanotubes: an experimental and theoretical selectivity study

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Abstract

The reaction of neutral single-walled carbon nanotubes (SWCNTs) with diazonium salts proceeds with a high selectivity towards metallic carbon nanotube species; this reaction is well-understood and the mechanism has been elucidated. In the present joint theoretical and experimental study, we investigate the reaction of negatively charged SWCNTs – carbon nanotubides – with diazonium salts. Our density functional theory calculations predict a stronger binding of the aryl diazonium cations to charged metallic SWCNTs species and therefore lead to a preferential addend binding in the course of the reaction. The Raman resonance profile analysis on the reductive arylation of carbon nanotubides obtained by the solid state intercalation approach with potassium in varying concentrations confirms the predicted preferred functionalization of metallic carbon nanotubes. Furthermore, we were also able to show that the selectivity for metallic SWCNT species could be further increased when low potassium concentrations (K : C < 1 : 200) are used for an initial selective charging of the metallic species. Further insights into the nature of the bound addends were obtained by coupled thermogravimetric analysis of the functionalized samples.

Graphical abstract: Reductive diazotation of carbon nanotubes: an experimental and theoretical selectivity study

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Publication details

The article was received on 21 Aug 2018, accepted on 21 Oct 2018 and first published on 22 Oct 2018


Article type: Edge Article
DOI: 10.1039/C8SC03737J
Citation: Chem. Sci., 2019,10, 706-717
  • Open access: Creative Commons BY license
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    Reductive diazotation of carbon nanotubes: an experimental and theoretical selectivity study

    M. Schirowski, C. Tyborski, J. Maultzsch, F. Hauke, A. Hirsch and J. Goclon, Chem. Sci., 2019, 10, 706
    DOI: 10.1039/C8SC03737J

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