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Open AccessArticle

Ullmann Reactions of Carbon Nanotubes—Advantageous and Unexplored Functionalization toward Tunable Surface Chemistry

1
Department of Organic Chemistry, Bioorganic Chemistry and Biotechnology, Silesian University of Technology, Krzywoustego 4, 44-100 Gliwice, Poland
2
Institute of Physics—CSE, Silesian University of Technology, Konarskiego 22B, 44-100 Gliwice, Poland
3
Faculty of Chemistry, Physicochemistry of Carbon Materials Research Group, Nicolaus Copernicus University in Toruń, Gagarin Street 7, 87-100 Toruń, Poland
*
Author to whom correspondence should be addressed.
Nanomaterials 2019, 9(11), 1619; https://doi.org/10.3390/nano9111619
Received: 1 October 2019 / Revised: 4 November 2019 / Accepted: 12 November 2019 / Published: 15 November 2019
(This article belongs to the Special Issue Carbon Nanotube: Synthesis, Characteristics and Applications)
We demonstrate Ullmann-type reactions as novel and advantageous functionalization of carbon nanotubes (CNTs) toward tunable surface chemistry. The functionalization routes comprise O-, N-, and C-arylation of chlorinated CNTs. We confirm the versatility and efficiency of the reaction allowing functionalization degrees up to 3.5 mmol g−1 by applying both various nanotube substrates, i.e., single-wall (SWCNTs) and multi-wall CNTs (MWCNTs) of various chirality, geometry, and morphology as well as diverse Ullmann-type reagents: phenol, aniline, and iodobenzene. The reactivity of nanotubes was correlatable with the nanotube diameter and morphology revealing SWCNTs as the most reactive representatives. We have determined the optimized conditions of this two-step synthetic protocol as: (1) chlorination using iodine trichloride (ICl3), and (2) Ullmann-type reaction in the presence of: copper(I) iodide (CuI), 1,10-phenanthroline as chelating agent and caesium carbonate (Cs2CO3) as base. We have analyzed functionalized CNTs using a variety of techniques, i.e., scanning and transmission electron microscopy, energy dispersive spectroscopy, thermogravimetry, comprehensive Raman spectroscopy, and X-ray photoelectron spectroscopy. The analyses confirmed the purely covalent nature of those modifications at all stages. Eventually, we have proved the elaborated protocol as exceptionally tunable since it enabled us: (a) to synthesize superhydrophilic films from—the intrinsically hydrophobic—vertically aligned MWCNT arrays and (b) to produce printable highly electroconductive pastes of enhanced characteristics—as compared for non-modified and otherwise modified MWCNTs—for textronics. View Full-Text
Keywords: carbon nanotubes; functionalization; Ullmann reaction; chlorination; hydrophilization; electroconductive coatings carbon nanotubes; functionalization; Ullmann reaction; chlorination; hydrophilization; electroconductive coatings
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MDPI and ACS Style

Kolanowska, A.; Kuziel, A.W.; Jędrysiak, R.G.; Krzywiecki, M.; Korczeniewski, E.; Wiśniewski, M.; Terzyk, A.P.; Boncel, S. Ullmann Reactions of Carbon Nanotubes—Advantageous and Unexplored Functionalization toward Tunable Surface Chemistry. Nanomaterials 2019, 9, 1619. https://doi.org/10.3390/nano9111619

AMA Style

Kolanowska A, Kuziel AW, Jędrysiak RG, Krzywiecki M, Korczeniewski E, Wiśniewski M, Terzyk AP, Boncel S. Ullmann Reactions of Carbon Nanotubes—Advantageous and Unexplored Functionalization toward Tunable Surface Chemistry. Nanomaterials. 2019; 9(11):1619. https://doi.org/10.3390/nano9111619

Chicago/Turabian Style

Kolanowska, Anna; Kuziel, Anna W.; Jędrysiak, Rafał G.; Krzywiecki, Maciej; Korczeniewski, Emil; Wiśniewski, Marek; Terzyk, Artur P.; Boncel, Sławomir. 2019. "Ullmann Reactions of Carbon Nanotubes—Advantageous and Unexplored Functionalization toward Tunable Surface Chemistry" Nanomaterials 9, no. 11: 1619. https://doi.org/10.3390/nano9111619

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