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Programming Photodegradability into Vinylic Polymers via Radical Ring-Opening Polymerization |
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| Authors: | Phuong T Do Berwyck L J Poad Hendrik Frisch |
| Institution: | 1. School of Chemistry and Physics, Queensland University of Technology, 2 George Street, Brisbane, QLD-4000 Australia
Centre for Materials Science, Queensland University of Technology, 2 George Street, Brisbane, QLD-4000 Australia;2. School of Chemistry and Physics, Queensland University of Technology, 2 George Street, Brisbane, QLD-4000 Australia |
| Abstract: | Incorporation of photolabile moieties into the polymer backbone holds promise to remotely-control polymer degradation. However, suitable synthetic avenues are limited, especially for radical polymerizations. Here we report a strategy to program photodegradability into vinylic polymers by exploiting the wavelength selectivity of photocycloadditions for radical ring-opening polymerization (rROP). Irradiation of coumarin terminated allylic sulfides with UVA light initiated intramolecular 2+2] photocycloaddition producing cyclic macromonomers. Subsequent RAFT-mediated rROP with methyl acrylate yielded copolymers that inherited the photoreactivity of the cyclic parent monomer. Irradiation with UVB initiated efficient photocycloreversion of the coumarin dimers, causing polymer degradation within minutes under UVB light or days under sunlight exposure. Our synthetic strategy may pave the way to insert photolabile linkages into vinylic polymers, tuning degradation for specific wavelengths. |
| Keywords: | Coumarin Ion Mobility-Mass Spectrometry Photodegradable Polymer Ring-Opening Polymerization Sunlight Degradable Polymer |