Nucleophilic Thiol-yne reaction in Macromolecular Engineering: From synthesis to applications

Dağlar, Özgün; Luleburgaz, Serter; Baysak, Elif; Gunay, Ufuk Saim; Hızal, Gürkan; Tunca, Ümit; Durmaz, Hakan

doi:10.1016/j.eurpolymj.2020.109926

Cited by 50 publications

(34 citation statements)

References 114 publications

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“…Thiol-yne coupling can occur through radical or nucleophile pathways. In this review, we focus on the nucleophilic mediated thiol-yne addition reaction, highly suitable for hydrogel synthesis because of its efficiency and rapid nature [ 82 ] ( Figure 5 d). HA-SH may react with PEG-yne derivatives displaying different architectures to afford hydrogels in a few minutes.…”

Section: Overview Of Ha Crosslinking Reactions Carried Out At Physiological Conditionsmentioning

confidence: 99%

Hyaluronic Acid Hydrogels Crosslinked in Physiological Conditions: Synthesis and Biomedical Applications

et al. 2021

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Hyaluronic acid (HA) hydrogels display a wide variety of biomedical applications ranging from tissue engineering to drug vehiculization and controlled release. To date, most of the commercially available hyaluronic acid hydrogel formulations are produced under conditions that are not compatible with physiological ones. This review compiles the currently used approaches for the development of hyaluronic acid hydrogels under physiological/mild conditions. These methods include dynamic covalent processes such as boronic ester and Schiff-base formation and click chemistry mediated reactions such as thiol chemistry processes, azide-alkyne, or Diels Alder cycloaddition. Thermoreversible gelation of HA hydrogels at physiological temperature is also discussed. Finally, the most outstanding biomedical applications are indicated for each of the HA hydrogel generation approaches.

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Section: Overview Of Ha Crosslinking Reactions Carried Out At Physiological Conditionsmentioning

confidence: 99%

Hyaluronic Acid Hydrogels Crosslinked in Physiological Conditions: Synthesis and Biomedical Applications

et al. 2021

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“…[ 19 ] Besides the rapid reaction between thiols and alkyl bromides, thiol‐ene/yne, p ‐fluoro‐thiol and thiol‐Michael reactions are extensively used in polymer chemistry to synthesize sophisticated polymer architectures. [ 20–23 ]…”

Section: Code Thiol Equiv Of [Ini]:[sh] Mnsec [Da] đ Deconvolution mentioning

confidence: 99%

“…[19] Besides the rapid reaction between thiols and alkyl bromides, thiol-ene/yne, p-fluoro-thiol and thiol-Michael reactions are extensively used in polymer chemistry to synthesize sophisticated polymer architectures. [20][21][22][23] Star-shaped polymers display unique physical properties, which are different from their linear counterparts. Therefore, star polymers are subject to intensive research for applications in gene and drug delivery, viscosity modifiers and catalysis among others.…”

mentioning

confidence: 99%

Thiol‐Bromo Click Reaction for One‐Pot Synthesis of Star‐Shaped Polymers

Beyer

Cattoz

Becer

2020

Macromol. Rapid Commun.

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Star‐shaped polymers have unique physical properties and they are sought after materials in industry. However, the ease of synthesis is essential for translation of these materials into large‐scale applications. Herein, a highly efficient synthetic method to prepare star‐shaped polymers by combination of Cu‐mediated reversible deactivation radical polymerization (Cu‐RDRP) and thiol‐bromo click reaction is described. Well‐defined linear and block polymers with a very high bromine chain end fidelity are obtained via Cu‐RDRP and subsequently react with multi‐functional thiol compounds. High coupling efficiencies of larger than 90% are obtained owing to the quick and efficient reaction between thiols and alkyl bromides. Moreover, the arms of the obtained star‐shaped polymers are linked via thioether bonds to the core, making them susceptible for oxidative degradation.

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“…[25][26][27][28][29] In our previous works, we have shown electron-deficient alkyne-containing polymers to be unique advanced materials, which can be easily modified via aza-Michael, thiol-Michael, Diels Alder, and metal-free azide cycloaddition reactions. [30][31][32][33][34][35] Moreover, we have also demonstrated that the esters of acetylene dicarboxylic acid can be reacted with a variety of dithiols to prepare polythioethers with high yields and high molecular weights under mild conditions. [36][37][38][39] In this work, we synthesized three derivatives of diallyl ester of acetylene dicarboxylic acid (ACDAE), by utilizing aza-Michael, thio-Michael, and metal-free azide-alkyne cycloaddition reactions.…”

Section: Introductionmentioning

confidence: 99%

Acetylene Dicarboxylic Acid Diallyl Ester: A Versatile Monomer for Thiol–Ene Photocured Networks

Dağlar

Çakmakçı

Gunay

et al. 2021

Macro Materials & Eng

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Thiol-ene photopolymerization (TEP) is a highly advantageous method for the curing of unsaturated monomers, and the design of novel monomers to be used in TEP is an active area of research. The feasibility and the versatility of novel acetylene dicarboxylic acid diallyl ester (ACDAE)-based monomers are synthesized and demonstrated. The electron deficient acetylenic core in ACDAE allows to apply three different click reactions, aza-Michael, thio-Michael, and metal-free azide-alkyne cycloaddition reactions, efficiently on it. Thus, three novel allylic monomers are synthesized and are used to prepare thiol-ene photopolymerized networks. All monomers are synthesized in good yields and structurally characterized by 1 H NMR and Fourier-transform infrared spectroscopy (FTIR) measurements. Thermal, thermomechanical, and mechanical properties, flame retardancy, transmittance, and the wettability of the networks are determined.

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Nucleophilic Thiol-yne reaction in Macromolecular Engineering: From synthesis to applications

Cited by 50 publications

References 114 publications

Hyaluronic Acid Hydrogels Crosslinked in Physiological Conditions: Synthesis and Biomedical Applications

Hyaluronic Acid Hydrogels Crosslinked in Physiological Conditions: Synthesis and Biomedical Applications

Thiol‐Bromo Click Reaction for One‐Pot Synthesis of Star‐Shaped Polymers

Acetylene Dicarboxylic Acid Diallyl Ester: A Versatile Monomer for Thiol–Ene Photocured Networks

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