Light-triggered chemical amplification to accelerate degradation and release from polymeric particles

Olejniczak, Jason; Huu, Viet Anh Nguyen; Lux, Jacques; Grossman, Madeleine; He, Sha; Almutairi, Adah

doi:10.1039/c5cc06143a

Cited by 20 publications

(15 citation statements)

References 49 publications

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“…suggesting that hydrazine induced non-specific cleavage of the terminal carbonate or the pendant esters, which could subsequently trigger backbone cleavage and depolymerization. 59 This could be caused by the basicity or nucleophilicity of hydrazine. Thus, DTT was investigated as a trigger.…”

Section: Development Of Redox-responsive Petgmentioning

confidence: 99%

End-Capping Strategies for Triggering End-to-End Depolymerization of Polyglyoxylates

2016

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Polymers that undergo end-to-end depolymerization in response to the cleavage of a stimuli-responsive end-cap are promising for diverse applications from drug delivery to responsive coatings and plastics. It is critical that the end-cap is designed to respond to an appropriate stimulus for the application. In the current work, end-caps for triggering the depolymerization of poly(ethyl glyoxylate) (PEtG) were explored. First a phenylboronate, a disulfide, and an azobenzene were utilized to impart redox-responsive properties to PEtG. Then, methoxy-substituted trityl groups were used to provide sensitivity to mild acid. A multi-responsive platform was also introduced, allowing PEtG to respond to multiple stimuli, either simultaneously or independently. Incorporation of a cross-linkable trialkene end-cap enabled the preparation of networks that could subsequently be depolymerized. Finally, high molar mass PEtG could be depolymerized by mechanical stimulation independent of the end-cap. It is anticipated that the versatility in end-capping strategies and potential depolymerization stimuli will not only expand PEtG's utility for different applications, but will also be useful for other classes of end-to-end depolymerizable polymers.

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Section: Development Of Redox-responsive Petgmentioning

confidence: 99%

End-Capping Strategies for Triggering End-to-End Depolymerization of Polyglyoxylates

2016

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“…Depolymerizable and related SIPs have garnered significant attention with respect to stimuli-controlled disassembly of macromolecular structures. [1][2][3][4][5][6][7][8][9][10][11][12] The term self-immolative polymer refers to a class of macromolecules that undergo linear depolymerization of the main chain greater than 10 repeat units, Scheme 1. A) Phillips et al synthesis of end-capped poly(phthalaldehydes) and self-immolation of the designed polymer.…”

Section: Introductionmentioning

confidence: 99%

Stimuli‐Responsive Depolymerization of Poly(Phthalaldehyde) Copolymers and Networks

Soars

Kamps

Fairbanks

et al. 2021

Macro Chemistry & Physics

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This article describes a stimuli-responsive cross-linked network based on a poly(phthalaldehyde) (PPA) self-immolating polymer backbone which, upon removal of polymer end-caps, becomes degradable under ambient conditions. Self-immolating polymers (SIPs) are of particular interest due to their ability to undergo controlled depolymerization resulting in the elimination of the polymer structure and potential recovery and reuse of the original monomers. Linear copolymers of phthalaldehyde and unsymmetrical allylated-phthalaldehyde monomers are obtained via anionic polymerization with appreciable incorporation of the allyl-functional monomeric units. This approach enables crosslinking of the otherwise linear polymers via thiol-ene reactions with the allyl functional phthalaldehyde polymers. The polymer network thus formed unzips along the phthalaldehyde backbone to yield monomers and low molecular weight fragments in response to chemical (F − , H + ) or physical (light, sonication) stimuli that remove the stabilizing functional endcaps on the phthalaldehyde polymers. Rheology is used to demonstrate gelation within 5 s of light exposure of the allylated-phthalaldehyde polymers reacted with pentaerythritol tetrakis(3-mercaptopropionate) and photoinitiator (3 wt%). Triggerable degelation makes this material well suited for photolithography and additive manufacturing as well as other applications that necessitate polymer network degradation or elimination. Further, a method is described for determining the degelation temperature of a self-immolative cross-linked network.

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“…9,10 Stimuli-responsive polymers that can respond to external stimuli through degradation have been proposed as potential alternatives to polyesters. 11,12 Systems responsive to changes in pH 13,14 or temperature, 15 oxidation, 16 reduction, 17 light 18 and other stimuli have been explored and promising results have been achieved, particularly in drug delivery. Over the past decade, a new class of stimuli-responsive polymers, often referred to as "self-immolative polymers" (SIPs) has emerged.…”

Section: Introductionmentioning

confidence: 99%

Tuning the hydrophobic cores of self-immolative polyglyoxylate assemblies

et al. 2018

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Light-triggered chemical amplification to accelerate degradation and release from polymeric particles

Abstract: We describe a means of chemical amplification to accelerate triggered degradation of a polymer and particles composed thereof.

Cited by 20 publications

References 49 publications

End-Capping Strategies for Triggering End-to-End Depolymerization of Polyglyoxylates

End-Capping Strategies for Triggering End-to-End Depolymerization of Polyglyoxylates

Stimuli‐Responsive Depolymerization of Poly(Phthalaldehyde) Copolymers and Networks

Tuning the hydrophobic cores of self-immolative polyglyoxylate assemblies

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