Depolymerizable poly(benzyl ether)-based materials for selective room temperature recycling

Baker, Matthew S.; Kim, Hyungwoo; Olah, Michael G.; Lewis, Gregory G.; Phillips, Scott T.

doi:10.1039/c5gc01090j

Cited by 56 publications

(59 citation statements)

References 27 publications

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“…53 Furthermore, poly(benzyl ether)s could be selectively depolymerized in the presence of polystyrene or polypropylene and then the monomers could be selectively dissolved, purified by extraction, and then repolymerized. 54 To the best of our knowledge, in comparison with PEtG, there is no other polymer that has been depolymerized and repolymerized through such a simple process under mild conditions.…”

Section: Resultsmentioning

confidence: 99%

Photocontrolled Degradation of Stimuli-Responsive Poly(ethyl glyoxylate): Differentiating Features and Traceless Ambient Depolymerization

et al. 2016

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The depolymerization of coatings prepared from a 6-nitroveratryl carbonate end-capped poly(ethyl glyoxylate) (PEtG) self-immolative polymer was studied. This polymer undergoes end-to-end depolymerization following cleavage of the end-cap by UV light. Several important fundamental differences between this class of polymers and conventional degradable polymers were revealed. For example, polymer backbone cleavage and depolymerization exhibited different dependencies on pH, emphasizing the decoupling of these processes. Probing of the coating erosion mechanism illustrated an interesting combination of features from surface erosion and bulk degradation mechanisms that arise from the end-to-end depolymerization mechanism and further differentiate these polymers from convention degradable polymers. It was also demonstrated that unlike backbone cleavage, PEtG depolymerization did not exhibit a dependence on water, and that PEtG could depolymerize back to the volatile monomer ethyl glyoxylate at ambient temperature and pressure. This unusual feature was utilized to perform facile polymer reprogramming/recycling via an irradiation-trapping-repolymerization sequence as well as polymer patterning by a simple irradiation-evaporation sequence.

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Section: Resultsmentioning

confidence: 99%

Photocontrolled Degradation of Stimuli-Responsive Poly(ethyl glyoxylate): Differentiating Features and Traceless Ambient Depolymerization

et al. 2016

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“…[128][129] SIPs can also be depolymerized back to monomers for reprocessing using preprogrammed triggers. [130][131] Ultimately, smart polymer approaches have potential to enable polymers to retain stability as desired during their use, but degrade on command. In addition, while some of the first synthetic polymers were developed to replace natural biopolymers, ironically there is now great interest in replacing synthetic polymers with biobased polymers.…”

Section: Does the Field Of Macromolecules Encompass Service Tools Or mentioning

confidence: 99%

Reflections on the Evolution of Smart Polymers

Gillies

2019

Israel Journal of Chemistry

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Since Staudinger's recognition that polymers were long chain molecules with covalent bonds between repeating units, the field has evolved tremendously. In addition to their many structural roles, polymers have been developed to exhibit “smart” stimuli‐responsive behavior. This article will describe the evolution of selected classes of smart polymers including those responsive to changes in pH, temperature, light, and mechanical stimuli, as well as self‐immolative polymers and their application in drug delivery, sensors, and actuators. It will also highlight key advancements in polymer chemistry that enabled rapid progress over the past ∼20 years. Whether the key achievements were predictable will be discussed, and the extent to which polymer science remains an independent science versus a service tool will be addressed. Finally, some possibilities for the evolution of the field over the next 20–30 years will be described.

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“…Notwithstanding, the examples of well-designed, biodegradable, functional polymers for PAI are still rare as far as we know. The use of other chemistry, such as continuous depolymerization [80][81][82] and dynamic physicochemical bonds or the formation of reversible and hierarchical structures of polymeric materials [83][84][85][86], would further provide new, biocompatible, degradation pathways of polymer structures without losing PA properties. In another example, a synthetic block copolymer that contains Pt(II) complexes was used [78].…”

Section: Functional Polymers As Pa Agentsmentioning

confidence: 99%

Biodegradable Contrast Agents for Photoacoustic Imaging

et al. 2018

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Over the past twenty years, photoacoustics—also called optoacoustics—have been widely investigated and, in particular, extensively applied in biomedical imaging as an emerging modality. Photoacoustic imaging (PAI) detects an ultrasound wave that is generated via photoexcitation and thermoelastic expansion by a short nanosecond laser pulse, which significantly reduces light and acoustic scattering, more than in other typical optical imaging and renders high-resolution tomographic images with preserving high absorption contrast with deep penetration depth. In addition, PAI provides anatomical and physiological parameters in non-invasive manner. Over the past two decades, this technique has been remarkably developed in the sense of instrumentation and contrast agent materials. In this review, we briefly introduce state-of-the-art multiscale imaging systems and summarize recent progress on exogenous bio-compatible and -degradable agents that address biomedical application and clinical practice.

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Depolymerizable poly(benzyl ether)-based materials for selective room temperature recycling

Abstract: Straightforward modifications to quinone methide monomers creates self-immolative poly(benzyl ethers) that enable room temperature separation and recycling of plastics.

Cited by 56 publications

References 27 publications

Photocontrolled Degradation of Stimuli-Responsive Poly(ethyl glyoxylate): Differentiating Features and Traceless Ambient Depolymerization

Photocontrolled Degradation of Stimuli-Responsive Poly(ethyl glyoxylate): Differentiating Features and Traceless Ambient Depolymerization

Reflections on the Evolution of Smart Polymers

Biodegradable Contrast Agents for Photoacoustic Imaging

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