Hetero diels-alder chemistry for the functionalization of single-walled carbon nanotubes with cyclopentadienyl end-capped polymer strands

Zydziak, N., Preuss, C. M., Winkler, V., Bruns, M., Hübner, C., & Barner-Kowollik, C. (2013) Hetero diels-alder chemistry for the functionalization of single-walled carbon nanotubes with cyclopentadienyl end-capped polymer strands. Macromolecular Rapid Communications, 34(8).

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Abstract

Single-walled carbon nanotubes (SWCNTs) are pre-functionalized with a pyridinyl-based dithioester to undergo a hetero Diels-Alder (HDA) reaction with cyclopentadienyl end-capped poly(methyl)methacrylate (Mn = 2700 g mol-1, PDI = 1.14). Fourier transform infrared spectroscopy, thermogravimetric analysis, elemental analysis (EA), and X-ray photoelectron spectroscopy (XPS) evidence the success of the grafting process. The estimated resulting grafting density (from XPS and EA) via the HDA reaction increases by a factor of more than two (0.0774 chains·nm-2 via XPS) compared with typical values obtained via a direct cyclopentadiene driven Diels-Alder conjugation onto non-functional SWCNTs under similar conditions. Cyclopentadienyl end-capped polymer strands react at the surface of pre-functionalized single-walled carbon nanotubes with a pyridine-based dithioester through a hetero Diels-Alder reaction. Elemental analysis and X-ray photoelectron spectroscopy are employed to determine the grafting density. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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ID Code: 99372
Item Type: Journal Article
Refereed: Yes
Additional Information: Cited By :7
Export Date: 5 September 2016
CODEN: MRCOE
Correspondence Address: Barner-Kowollik, C.; Preparative Macromolecular Chemistry, Institut für Technische Chemie und Polymerchemie, Karlsruhe Institute of Technology (KIT), Engesserstr. 18, 76128 Karlsruhe, Germany; email: christopher.barner-kowollik@kit.edu
Chemicals/CAS: poly(methyl methacrylate), 39320-98-4, 9008-29-1; pyridine, 110-86-1; thiol derivative, 13940-21-1; Cyclopentanes; Nanotubes, Carbon; Polymethyl Methacrylate, 9011-14-7; Pyridines; Sulfhydryl Compounds; pyridine, NH9L3PP67S
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Keywords: cyclopentadiene, grafting density, hetero Diels-Alder reaction, poly(methyl)methacrylate, single-walled carbon nanotubes, Cyclopentadienes, Cyclopentadienyls, Functionalizations, Grafting densities, Grafting process, Polymer strands, Single-walled carbon nanotube (SWCNTs), Directive antennas, Fourier transform infrared spectroscopy, Olefins, Photoelectrons, Single-walled carbon nanotubes (SWCN), Thermogravimetric analysis, X ray photoelectron spectroscopy, Grafting (chemical), carbon nanotube, cyclopentane derivative, poly(methyl methacrylate), pyridine, pyridine derivative, thiol derivative, article, chemistry, cycloaddition, esterification, oxidation reduction reaction, Cycloaddition Reaction, Cyclopentanes, Nanotubes, Carbon, Oxidation-Reduction, Polymethyl Methacrylate, Pyridines, Sulfhydryl Compounds
DOI: 10.1002/marc.201300025
ISSN: 10221336
Divisions: Current > Schools > School of Chemistry, Physics & Mechanical Engineering
Current > Institutes > Institute for Future Environments
Current > QUT Faculties and Divisions > Science & Engineering Faculty
Deposited On: 22 Sep 2016 04:50
Last Modified: 29 Sep 2016 03:11

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