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Radical Departure: Thermally-Triggered Degradation of Azo-Containing Poly(β-thioester)s

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George and Josephine Butler Polymer Research Laboratory, Center for Macromolecular Science and Engineering, Department of Chemistry, Department of Chemical Engineering, and §J. Crayton Pruitt Family Department of Biomedical Engineering, University of Florida, P.O. Box 117200, Gainesville, Florida, United States
Cite this: ACS Macro Lett. 2016, 5, 6, 688–693
Publication Date (Web):May 19, 2016
Copyright © 2016 American Chemical Society

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    The design and synthesis of a new class of thermally-labile poly(β-thioester)s is reported. Aliphatic azo linkages were incorporated into the main chain of the polymers to allow for degradation to lower molecular weights upon heating. These polymers displayed a temperature-dependent degradation profile with a significant increase in decomposition rate as the temperature was raised from 60 to 95 °C. This approach was further extended to prepare amphiphilic triblock copolymers containing poly(β-thioester)s and poly(ethylene glycol) (PEG). The resulting block copolymers were capable of self-assembly into micelles in water. Moreover, the assembled nanoparticles underwent dissociation as a result of exposure to heat.

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