Multi-olefin containing polyethers and triazolinediones: a powerful alliance

Johann, Tobias; Houck, Hannes A.; Dinh, Thi Ty Mai; Kemmer-Jonas, Ulrike; Prez, Filip Du; Frey, Holger

doi:10.1039/c9py00718k

Cited by 15 publications

(28 citation statements)

References 39 publications

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“…Bis-TAD reagents have also been envisaged for crosslinking polymers either along the backbone or through the side chains. [174][175][176][177][178][179][180][181] The thermal reversibility of the TAD-ene reaction with indole derivatives permits the network made by this chemistry to be healable and remoldable. 179 The high efficiency of TAD-based click chemistry allows surface modification to be completed within minutes, 182,183 while the TAD transclick reaction enables the preparation of rewritable polymer brush micropatterns.…”

Section: Future Developmentsmentioning

confidence: 99%

“…This is an opportunity as main reaction partner of TAD are alkene and electron rich aromatic systems, which are abundant in both natural and synthetic polymers. TAD crosslinking applications can therefore involve (i) Alder-ene reaction with polymer containing isolated alkene 180,492,493 or indole, 177,178 (ii) DielsÀAlder reaction 494 with polymer containing conjugated diene, 174,180,181,494,495 and (iii) electrophilic aromatic substitution with phenol in polypeptide containing tyrosine derivatives. 172 The reversible bond between indole and TAD in Alder-ene reaction has inspired the "transclick" concept.…”

Section: Tad Crosslinkingmentioning

confidence: 99%

“…Similarly, a range of unsaturated polyesters, 174,492 poly(glycidyl ether)s 180 and polycarbonates 181 were synthesized by organocatalyzed ROP followed by quantitative and irreversible functionalization with TAD.…”

Section: Diels-alder and Tad Clickmentioning

confidence: 99%

“…A unique feature of TAD click chemistry is its utility for functionalizing polymers prepared by ring‐opening metathesis polymerization (ROMP) and acyclic diene metathesis (ADMET) as these polymers contain dienes and/or alkenes in backbones and/or side chains. Bis‐TAD reagents have also been envisaged for crosslinking polymers either along the backbone or through the side chains 174–181 . The thermal reversibility of the TAD‐ene reaction with indole derivatives permits the network made by this chemistry to be healable and remoldable 179 .…”

Section: Click Chemistries Employed In Polymerization and Polymer Modificationmentioning

confidence: 99%

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Click chemistry strategies for the accelerated synthesis of functional macromolecules

Geng

Shin

et al. 2021

Journal of Polymer Science

184

114

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Click chemistry is one of the most powerful strategies for constructing polymeric soft materials with precise control over architecture and functionality. In this review, we provide a comprehensive summary of the state-of-the art for synthesizing functional polymers and their expanding range of applications. The synthetic and mechanistic aspects are discussed for key reactions that fulfill "click" requirements and their applications in construction of macromolecules with linear, branched, and other complex architectures are described.

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Section: Future Developmentsmentioning

confidence: 99%

Section: Tad Crosslinkingmentioning

confidence: 99%

Section: Diels-alder and Tad Clickmentioning

confidence: 99%

Section: Click Chemistries Employed In Polymerization and Polymer Modificationmentioning

confidence: 99%

See 2 more Smart Citations

Click chemistry strategies for the accelerated synthesis of functional macromolecules

Geng

Shin

et al. 2021

Journal of Polymer Science

184

114

View full text Add to dashboard Cite

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“…Next, we explored the scope of the TBD‐catalyzed transesterification reaction of PMA, by replacing BnOH with a series of unsaturated primary alcohols, viz., allyl alcohol (AllylOH), propargyl alcohol (propargylOH), citronellol, furfuryl alcohol (furfurylOH), and sorbinol. These functional substrates are of considerable interest as they enable subsequent thiol‐ene, [ 44 ] CuAAc, [ 6 ] Alder‐ene, [ 45 ] and Diels–Alder reactions, [ 45,46 ] respectively.…”

Section: Figurementioning

confidence: 99%

Stoichiometric Control over Partial Transesterification of Polyacrylate Homopolymers as Platform for Functional Copolyacrylates

Guyse

Bernhard

Hoogenboom

2020

Macromol. Rapid Commun.

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Only recently, post‐polymerization modification reactions of unactivated polyacrylates have been emerging as an attractive alternative to utilizing reactive monomers, enabling the synthetic upcycling of these widely applied polymers. Within this contribution, the triazabicyclodecene‐catalyzed transesterification of polyacrylates is reported, including the reaction kinetics and the broad scope for macromolecular design of functional copolyacrylates. More specifically, the transesterification is performed under equilibrium conditions with a set of primary alcohols whereby the reaction kinetics and the obtained conversion as a function of stoichiometric excess of alcohol are evaluated. The results show that the obtained conversion is dependent on the polarity of the solvent and of the alcohol. Through this approach, the transesterification degree can be accurately controlled by stoichiometry, enabling the precise modulation of the macromolecular structure. Finally, the utility of this approach is demonstrated to incorporate functional side chains that are incompatible with radical polymerization, to facilitate Diels–Alder and thiol‐ene reactions, enabling access to a broad range of functional materials from simple polyacrylate homopolymer precursors.

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Visible Light Conjugation with Triazolinediones as a Route to Degradable Poly(ethylene glycol)–Lipids for mRNA Lipid Nanoparticle Formulation

et al. 2023

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Polyethylene glycol (PEG) is considered as the gold standard for colloidal stabilization of nanomedicines, yet PEG is non-degradable and lacks functionality on the backbone. Herein, we introduce concomitantly PEG backbone functionality and degradability via a one-step modification with 1,2,4triazoline-3,5-diones (TAD) under green light. The TAD-PEG conjugates are degradable in aqueous medium under physiological conditions, with the rate of hydrolysis depending on pH and temperature. Subsequently, a PEG-lipid is modified with TAD-derivatives and successfully used for messenger RNA (mRNA) lipid nanoparticle (LNP) delivery, thereby improving mRNA transfection efficiency on multiple cell cultures in vitro. In vivo, in mice, mRNA LNP formulation exhibited a similar tissue distribution as common LNPs, with a slight decrease in transfection efficiency. Our findings pave the road towards the design of degradable, backbonefunctionalized PEG for applications in nanomedicine and beyond.

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Multi-olefin containing polyethers and triazolinediones: a powerful alliance

Abstract: Multi-functional polyethers with ene or diene moieties were prepared via the polymerisation of tailored functional glycidyl ether monomers to create a platform for click chemistry with triazolinediones (TADs).

Cited by 15 publications

References 39 publications

Click chemistry strategies for the accelerated synthesis of functional macromolecules

Click chemistry strategies for the accelerated synthesis of functional macromolecules

Stoichiometric Control over Partial Transesterification of Polyacrylate Homopolymers as Platform for Functional Copolyacrylates

Visible Light Conjugation with Triazolinediones as a Route to Degradable Poly(ethylene glycol)–Lipids for mRNA Lipid Nanoparticle Formulation

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