Jump to main content
Jump to site search

Issue 3, 2019
Previous Article Next Article

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

Author affiliations

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

Back to tab navigation

Supplementary files

Article information


Submitted
21 Aug 2018
Accepted
21 Oct 2018
First published
22 Oct 2018

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2019,10, 706-717
Article type
Edge Article

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

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. Material from this article can be used in other publications provided that the correct acknowledgement is given with the reproduced material.

Reproduced material should be attributed as follows:

  • For reproduction of material from NJC:
    [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC.
  • For reproduction of material from PCCP:
    [Original citation] - Published by the PCCP Owner Societies.
  • For reproduction of material from PPS:
    [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC.
  • For reproduction of material from all other RSC journals:
    [Original citation] - Published by The Royal Society of Chemistry.

Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.


Social activity

Search articles by author

Spotlight

Advertisements