Rewritable Polymer Brush Micropatterns Grafted by Triazolinedione Click Chemistry

Roling, Oliver; Bruycker, Kevin De; Vonhören, Benjamin; Stricker, Lucas; Körsgen, Martin; Arlinghaus, Heinrich F.; Ravoo, Bart Jan; Prez, Filip Du

doi:10.1002/anie.201506361

Cited by 91 publications

(91 citation statements)

References 29 publications

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“…While TAD‐mediated conjugation of tyrosine in natural proteins is feasible, the applicability of this chemistry in synthetic polymers was explored by Stadler and Kuhrau and more recently by DuPrez and co‐workers . The group reported ultrafast reversible TAD click reactions of polyacrylates with indole groups to create dynamic polymer networks . The same group also applied a difunctional TAD for the cross‐linking of various unsaturated plant oils to produce films and particles …”

Section: Introductionmentioning

confidence: 99%

Exploring Tyrosine‐Triazolinedione (TAD) Reactions for the Selective Conjugation and Cross‐Linking of N‐Carboxyanhydride (NCA) Derived Synthetic Copolypeptides

Hanay

Ritzen

Brougham

et al. 2017

Macromolecular Bioscience

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Highly efficient functionalization and cross-linking of polypeptides is achieved via tyrosine-triazolinedione (TAD) conjugation chemistry. The feasibility of the reaction is demonstrated by the reaction of 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD) with tyrosine containing block copolymer poly(ethylene glycol)-Tyr as well as a statistical copolymer of tyrosine and lysine (poly(Lys -st-Tyr )) prepared form N-carboxyanhydride polymerization. Selective reaction of PTAD with the tyrosine units is obtained and verified by size exclusion chromatography and NMR spectroscopy. Moreover, two monofunctional and two difunctional TAD molecules are synthesized. It is found that their stability in the aqueous reaction media significantly varied. Under optimized reaction conditions selective functionalization and cross-linking, yielding polypeptide hydrogels, can be achieved. TAD-mediated conjugation can offer an interesting addition in the toolbox of selective (click-like) polypeptide conjugation methodologies as it does not require functional non-natural amino acids.

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Section: Introductionmentioning

confidence: 99%

Exploring Tyrosine‐Triazolinedione (TAD) Reactions for the Selective Conjugation and Cross‐Linking of N‐Carboxyanhydride (NCA) Derived Synthetic Copolypeptides

Hanay

Ritzen

Brougham

et al. 2017

Macromolecular Bioscience

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“…TADs are one of the most reactive (di)enophiles and show quantitative conversions at room temperature with isolated alkenes or conjugated dienes, respectively in an Alder-ene or Diels-Alder reaction. TAD has recently been applied in a wide range of applications, such as self-healing, 19 surface chemistry, [20][21][22] and post-modification of unsaturated ADMET polymers. 23 This is the first report on the post-modification of PPEs via their internal double bonds for tuning their thermal properties.…”

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confidence: 99%

Triazolinedione-“clicked” poly(phosphoester)s: systematic adjustment of thermal properties

et al. 2017

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The thermal properties of halogen-free flame retardant poly(phosphoester)s from acyclic diene metathesis polycondensation have been optimized by a systematic post-modification using 1,2,4-triazoline-3,5-dione derivatives. The straightforward modification not only increased their glass transition temperatures significantly but also improved the thermal stability with respect to their char yields.Poly( phosphoester)s (PPEs) can be prepared via both ringopening polymerization and polycondensation.1,2 We recently applied ADMET polycondensation to prepare a variety of PPEs. [3][4][5][6] Currently, PPEs are studied in biomedical applications for their biocompatibility, 7 biodegradability and adjus- show higher resistance to leaching and migration, compared to low molecular weight additives. 9 Indeed, phosphorus is an efficient char promoter forming an accumulated protective layer on the materials surface, which limits the release of fuel to the flame. 10,11 Additionally, PPEs typically show low toxicity or almost smoke-free burning. 12,13 Recently, the combination of phosphorus-containing flame retardants with nitrogen compounds has attracted much attention. The combination of both elements physically and chemically can dramatically improve the action of the phosphorus species in the condensed phase upon combustion. 14,15 Nitrogen compounds are believed to act by the release of inert gases or by the promotion of char formation as a result of a condensation reaction.Besides phosphorus and nitrogen, the introduction of aromatic structures is also often mentioned to promote the charring. 16As a systematic study on the thermal properties and char yield, with structural variation of the main-and side chains of PPEs, is missing in the current literature, the main goal of this research was the preparation of modified PPEs via ADMET polycondensation, as a result of the variation of both the backbone and side chains. Furthermore, we used the efficient, recently revisited "click chemistry" of 1,2,4-triazoline-3,5-diones (TAD) 17,18 to modify the double bonds along the PPE backbone to further adjust the material properties. This TADene chemistry can not only be applied as a reliable and convenient post-modification reaction of unsaturated polymers but will also introduce additional nitrogen atoms into the PPEs, which is expected to have a positive influence on their flame retardant performance. TADs are one of the most reactive (di)enophiles and show quantitative conversions at room temperature with isolated alkenes or conjugated dienes, respectively in an Alder-ene or Diels-Alder reaction. TAD has recently been applied in a wide range of applications, such as self-healing, 19 surface chemistry, 20-22 and post-modification of unsaturated ADMET polymers. 23This is the first report on the post-modification of PPEs via their internal double bonds for tuning their thermal properties. Supposing that TAD-modification can increase the glass transition temperature (T g ), this would undoubtedly broaden the range of applications for PPEs...

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“…End anchoring of polymer chains at a high density to a surface to form polymer brushes is a powerful way to prepare functional coatings . Fluorescent dye‐labeled polymer brushes have been prepared and utilized in ion sensing and organic light emitting diode (OLED) development or in studying the degrafting kinetics of brushes . In this context, responsive polymer brushes, which undergo conformational change upon certain, for example, pH, temperature, ionic strength, and solvent have been modified with fluorescent probes and widely used in the design of sensors .…”

Section: Introductionmentioning

confidence: 99%

Chain End‐Functionalized Polymer Brushes with Switchable Fluorescence Response

Taş

Kopeć

Pol

et al. 2019

Macro Chemistry & Physics

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Herein is described the switchable fluorescence response of poly(methyl methacrylate) (PMMA) brushes. Chain end fluorescein labeled PMMA brushes are prepared by combining surface‐initiated atom transfer radical polymerization (SI‐ATRP) with a copper‐catalyzed alkyne‐azide cycloaddition (CuAAC) click reaction. Successful attachment of fluorescein is confirmed by measuring fluorescence of the as‐prepared films. Utilizing co‐solvency of PMMA in isopropanol‐water mixtures, responsive behavior of the end‐functionalized brushes is demonstrated by measuring the changes in fluorescence intensity between the swollen and collapsed states.

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Rewritable Polymer Brush Micropatterns Grafted by Triazolinedione Click Chemistry

Cited by 91 publications

References 29 publications

Exploring Tyrosine‐Triazolinedione (TAD) Reactions for the Selective Conjugation and Cross‐Linking of N‐Carboxyanhydride (NCA) Derived Synthetic Copolypeptides

Exploring Tyrosine‐Triazolinedione (TAD) Reactions for the Selective Conjugation and Cross‐Linking of N‐Carboxyanhydride (NCA) Derived Synthetic Copolypeptides

Triazolinedione-“clicked” poly(phosphoester)s: systematic adjustment of thermal properties

Chain End‐Functionalized Polymer Brushes with Switchable Fluorescence Response

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