Chemical reaction networks based on conjugate additions on β′-substituted Michael acceptors

Spitzbarth, Benjamin; Eelkema, Rienk

doi:10.1039/d3cc02126b

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2024

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Cited by 2 publications

(1 citation statement)

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“…11,14–19 A recent review gives a timely overview of the subject. 20 One covalent dynamic system of particular interest to us was the addition of thiols to electron poor alkynones resulting in thiovinylketones (TVK) (Fig. 1a).…”

mentioning

confidence: 99%

Tuneable thiol exchange linkers for traceless drug release applications in prodrugs and ADCs

Walther,

Park,

Ashman

et al. 2024

Chem. Commun.

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mentioning

confidence: 99%

Tuneable thiol exchange linkers for traceless drug release applications in prodrugs and ADCs

Walther,

Park,

Ashman

et al. 2024

Chem. Commun.

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Vitrimer-like Elastomers with Rapid Stress-Relaxation by High-Speed Carboxy Exchange through Conjugate Substitution Reaction

Kohsaka,

Nishiie,

Kawatani

et al. 2024

Preprint

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We report the design of vitrimer-like elastomers that exhibit the fastest stress relaxation (τ = 2 s at 140 °C) among the reported poly(meth)acrylate-based vitrimers. The trick is the use of the carboxy exchange reaction by the conjugate substitution reaction using α-(acyloxymethyl) acrylate skeletons, which was inspired by our preliminary results in a small-molecule solution that showed the progress of the above carboxy exchange reaction, even at ambient temperature, in the presence of 1,4-diazabicyclo[2.2.2]octane (DABCO). To incorporate the quick bond rearrangement via carboxy exchange into the network, copolymers of ethyl acrylate and acrylic acid were crosslinked using bis[α-(bromomethyl)acrylates]. The cross-linked sample doped with 10 wt% DABCO exhibited processability to obtain a transparent film by hot pressing, despite the stable rubbery plateau in dynamic mechanical analysis. The high-speed bond exchange in the network was validated by stress-relaxation tests, where the stress-relaxation speed was 102–103 times faster than that of previously reported poly(meth)acrylate vitrimers operated by other common DCBs. The significantly fast relaxation ability eventually allows quick molding with household iron. In addition, the present material was applied as an adhesion sheet for plastics and metal substrates. Because dynamic cross-linking with the proposed bond exchange mechanism is implementable to any polymers bearing carboxy pendants, our approach can be applied to versatile backbones, which must thus be meaningful in the practical sense.

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Chemical reaction networks based on conjugate additions on β′-substituted Michael acceptors

Abstract: Over the last few decades, the study of more complex, chemical systems closer to those found in nature, and the interactions within those systems, has grown immensely. Despite great efforts,...

Cited by 2 publications

References 109 publications

Tuneable thiol exchange linkers for traceless drug release applications in prodrugs and ADCs

Tuneable thiol exchange linkers for traceless drug release applications in prodrugs and ADCs

Vitrimer-like Elastomers with Rapid Stress-Relaxation by High-Speed Carboxy Exchange through Conjugate Substitution Reaction

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