Functionalization of fullerenes with cyclopentadienyl and anthracenyl capped polymeric building blocks via Diels-Alder chemistry

Nebhani, L. & Barner-Kowollik, C. (2010) Functionalization of fullerenes with cyclopentadienyl and anthracenyl capped polymeric building blocks via Diels-Alder chemistry. Macromolecular Rapid Communications, 31(14).

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Abstract

Cyclopentadienyl (Cp) capped polymers [polyethylene glycols (PEGs), M n = 2 000 g mol-1], react readily with fullerenes in a 1:1 molar ratio (relative to the amount of fullerenes and Cpend groups) at ambient temperature within 5 min in the absence of any catalyst in a DielsAlder (DA) reaction to provide fullerene-PEG hybrids. Similarly, anthracenyl capped PEGs react with fullerenes (in a 1:3 molar ratio) in DA reactions to yield the corresponding hybrids, albeit over a period of 1.5 h at 80 °C and a lesser conversion. The efficiency of the transformation is monitored via electrospray ionization mass spectrometry (ESI-MS), demonstrating that the fullerenes can be transformed into polymer hybrids; most efficiently when Cp-functional polymer is used as the diene. In addition, the obtained hybrids were subjected to UV/Vis as well as thermogravimetric analysis further underpinning the formation of monosubstituted C60-PEG hybrids [wt.-%exp 70 ±5 (PEG), 30 ±5 (C60), wt.-%theo 68 (PEG), 32 (C 60)]. (Figure Presented) © 2010 WILEY-VCH Verlag GmbH & Co. KCaA, Weinheim.

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ID Code: 99252
Item Type: Journal Article
Refereed: Yes
Additional Information: Cited By :21
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), Engesserstraße 18, 76128 Karlsruhe, Germany; email: christopher.barner-kowollik@kit.edu
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Keywords: Cyclopentadienyl and anthracenyl capped polymers, Diels-Alder reactions, Electrospray ionization mass spectrometry (ESI-MS), Fullerenes, Poly(ethylene glycol), UV/Vis spectroscopy, Cyclopentadienyls, Diels-Alder reaction, Electrospray ionization mass spectrometry, UV/ Vis spectroscopy, Electrospray ionization, Ethylene, Ethylene glycol, Functional polymers, Ionization, Mass spectrometry, Particle detectors, Polyethylene oxides, Thermogravimetric analysis, Polyethylene glycols
DOI: 10.1002/marc.201000142
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: 07 Oct 2016 02:35

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