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Issue 12, 2016
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Green chain-shattering polymers based on a self-immolative azobenzene motif

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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.

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

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Publication details

The article was received on 04 Dec 2015, accepted on 21 Feb 2016 and first published on 22 Feb 2016


Article type: Paper
DOI: 10.1039/C5PY01937K
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Citation: Polym. Chem., 2016,7, 2272-2279
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    Green chain-shattering polymers based on a self-immolative azobenzene motif

    H. Mutlu and C. Barner-Kowollik, Polym. Chem., 2016, 7, 2272
    DOI: 10.1039/C5PY01937K

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