Green chain-shattering polymers based on a self-immolative azobenzene motif

Mutlu, H. & Barner-Kowollik, C. (2016) Green chain-shattering polymers based on a self-immolative azobenzene motif. Polymer Chemistry, 7(12).

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Abstract

A chain-shattering polymer system consisting of nontoxic, renewable resource-based monomers via acyclic diene metathesis (ADMET) chemistry is introduced. Amphiphilic triblock copolymers with apparent molecular weights in the range from 10 to 23 kDa are synthesized using a monofunctional polyethylene glycol monoacrylate, which acts as a selective chain-transfer agent during the polymerization process. Most importantly, the functional polymers possess repetitive midchain azobenzene moieties imparting them with self-immolative properties. By virtue of the enzyme degradable azobenzene chain elements, the amphiphilic macromolecules can be efficiently degraded via a self-immolative reaction into small fragments. The construction of the macromolecules along with their degradation is evidenced by nuclear magnetic resonance spectroscopy, electrospray ionization mass spectrometry and size exclusion chromatography. In addition, the triggered degradation leads to a strong reduction in the UV absorptivity of the polymeric material. © 2016 The Royal Society of Chemistry.

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ID Code: 99472
Item Type: Journal Article
Refereed: Yes
Additional Information: Cited By :1
Export Date: 5 September 2016
Correspondence Address: Barner-Kowollik, C.; Preparative Macromolecular Chemistry, Institut für Technische Chemie und Polymerchemie, Karlsruhe Institute of Technology (KIT), Engesserstr. 18, Germany; email: christopher.barner-kowollik@kit.edu
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Keywords: Azobenzene, Chromatography, Electrospray ionization, Macromolecules, Magnetic resonance spectroscopy, Mass spectrometry, Nuclear magnetic resonance spectroscopy, Size exclusion chromatography, Acyclic diene metathesis, Amphiphilic macromolecules, Amphiphilic triblock copolymers, Azobenzene moiety, Chain transfer agents, Electrospray ionization mass spectrometry, Polymerization process, Renewable resource, Chains
DOI: 10.1039/c5py01937k
ISSN: 17599954
Divisions: Current > Institutes > Institute for Future Environments
Current > QUT Faculties and Divisions > Science & Engineering Faculty
Deposited On: 22 Sep 2016 04:50
Last Modified: 28 Jun 2017 17:02

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