Thiol-Ene “Click Reactions” as a Promising Approach to Polymer Materials

Kazybayeva, D.S.; Irmukhametova, Galiya S.; Khutoryanskiy, Vitaliy V.

doi:10.1134/s1560090422010055

Cited by 14 publications

(8 citation statements)

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“…The chemical cross–link is conveniently achieved by functionalizing the hydroxyl moiety with aminoxy, hydrazide, acrylamide, thiol, and semicarbazide, cysteine moieties with maleimide and 2–halo acetyl . Apart from that, photo-initiated thiol–ene “click” reactions have recently gained attention for control network hydrogel formation. ,, The thiol–ene “click” hydrogels possess unique properties such as high water content, excellent biocompatibility, and tunable mechanical strength . They have found applications in various fields, including tissue engineering, drug delivery, and biosensing .…”

Section: Introductionmentioning

confidence: 99%

Structural and Transport Properties of Norbornene-Functionalized Poly(vinyl alcohol) “Click” Hydrogel: A Molecular Dynamics Study

Das

Kundu

2023

ACS Sustainable Chem. Eng.

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The thiol–norbornene cross–linked poly(vinyl alcohol) (PVA) “click” hydrogel is a synthetic and sustainable polymer chain that is widely used in the biomedical field. Molecular dynamics simulations are invoked to measure the hydrogel’s transport and structural properties that cannot be measured precisely by experimental techniques. There are three different forms of thiol–norbornene cross–linked PVA “click” hydrogel models constructed by replicating a representative unit cell of cross–linked PVA chains and immersing it into an aqueous environment. Additionally, the dynamics is compared with the movement of the PVA hydrogel in water. The AMBER14SB force field is utilized to describe the interatomic interactions. The system’s dynamic behavior is achieved in the grand canonical ensemble and the isobaric isothermal ensemble. The dynamics of the system exposes the vital role played by norbornene in securing the stability of PVA polymer chains, thus contributing significantly to the overall robustness of the hydrogel. Delving into the structural analysis of the radial distribution function provides insights into the emergence of compact clusters, where interactions between PVA polymer chains and water drive their formation. The PVA hydrogel functionalizes with norbornene and exhibits a superior swelling ratio compared with the other variant hydrogels considered here owing to the freezing water phenomenon. Conversely, the swelling ratio of the cross–linked PVA hydrogel diminishes due to the intricate process of structural self–assembly. Consequently, the cohesive force within the cross–linked PVA hydrogel structure intensifies, highlighting the profound influence of bolstered hydrogen bonding. The exploration from this study provides valuable insights into the behavior of thiol–norbornene “click” PVA hydrogels and the importance of chemical cross–linking. The thiol–norbornene “click” PVA hydrogel holds tremendous potential for applications across diverse scientific domains, heralding a new era of possibilities.

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Section: Introductionmentioning

confidence: 99%

Structural and Transport Properties of Norbornene-Functionalized Poly(vinyl alcohol) “Click” Hydrogel: A Molecular Dynamics Study

Das

Kundu

2023

ACS Sustainable Chem. Eng.

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“…7 The initiation occurs under the action of azo compounds, peroxides, and so forth or under UV irradiation, producing the thiyl radical RS and other side products. 7 Thiol-ene addition is suitable for monomer and polymer synthesis due to several advantages: tolerance to many different reaction conditions/solvents, clearly defined reaction pathways/ products, and facile synthetic strategies from a range of easily obtained starting materials. [8][9][10] Thiol-ene reactions can be induced photochemically (cleavage or H-abstraction type photoinitiators) or thermally at ambient temperature in the presence of oxygen without undesirable side reactions.…”

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

“…The “thiol‐ene” term indicates the addition of thiol to the double bond, irrespectively of the reaction mechanism (molecular or ionic) 7 . The thiol‐ene reactions are performed under the radical conditions occurring as a typical chain process involving the initiation, chain propagation, and termination stages 7 . The initiation occurs under the action of azo compounds, peroxides, and so forth or under UV irradiation, producing the thiyl radical RS and other side products 7 .…”

Section: Introductionmentioning

confidence: 99%

“…The thiol‐ene reactions are performed under the radical conditions occurring as a typical chain process involving the initiation, chain propagation, and termination stages 7 . The initiation occurs under the action of azo compounds, peroxides, and so forth or under UV irradiation, producing the thiyl radical RS and other side products 7 . Thiol‐ene addition is suitable for monomer and polymer synthesis due to several advantages: tolerance to many different reaction conditions/solvents, clearly defined reaction pathways/products, and facile synthetic strategies from a range of easily obtained starting materials 8–10 .…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of a renewable polyamine from canola oil by photocatalyzed thiol‐ene addition of cysteamine under green conditions

Echeverri

Inciarte

Cortés

et al. 2023

J of Applied Polymer Sci

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A renewable polyamine was obtained by the photocatalyzed thiol‐ene addition of cysteamine hydrochloride (CAHC) to canola oil under mild conditions, using green solvents, a simple reaction system and a low‐power 365 UV lamp. A comparison of four different solvents was performed and the effect of one‐step and stepwise addition of CAHC to the reaction mixture was investigated. The solubilities of CAHC and oil in the solvent played a crucial role in the conversion of double bonds due to diffusion limitations and also due to changes in the opacity of the reaction mixture. Isopropanol showed a good solubility balance, dissolving well the oil and at the same time partially dissolving CAHC. During the one‐step addition of CAHC, the maximum conversions achieved were of 38.2% and 69% (in 24 h) with ethanol and isopropanol as solvents, respectively. The selectivity to the thiol‐ene product was very high with both solvents (i.e., 88%–90% at 4 h). The stepwise addition of CAHC significantly improved the double bond conversion (i.e., 93% at 24 h) using isopropanol as solvent. Finally, the polyamine was used as a comonomer in the aminolysis of a fatty cyclic carbonate affording a fully biobased elastomeric polyhydroxyurethane (PHU).

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Bottom‐Up Synthesized Glucan Materials: Opportunities from Applied Biocatalysis

Zhong,

Nidetzky

2024

Advanced Materials

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Linear D‐glucans are natural polysaccharides of simple chemical structure. They are comprised of D‐glucosyl units linked by a single type of glycosidic bond. Noncovalent interactions within, and between, the D‐glucan chains give rise to a broad variety of macromolecular nanostructures that can assemble into crystalline‐organized materials of tunable morphology. Structure design and functionalization of D‐glucans for diverse material applications largely relies on top‐down processing and chemical derivatization of naturally derived starting materials. The top‐down approach encounters critical limitations in efficiency, selectivity, and flexibility. Bottom‐up approaches of D‐glucan synthesis offer different, and often more precise, ways of polymer structure control and provide means of functional diversification widely inaccessible to top‐down routes of polysaccharide material processing. Here we describe the natural and engineered enzymes (glycosyltransferases, glycoside hydrolases and phosphorylases, glycosynthases) for D‐glucan polymerization and show the use of applied biocatalysis for the bottom‐up assembly of specific D‐glucan structures. We further show advanced material applications of the resulting polymeric products and discuss their important role in the development of sustainable macromolecular materials in a bio‐based circular economy.This article is protected by copyright. All rights reserved

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Thiol-Ene “Click Reactions” as a Promising Approach to Polymer Materials

Abstract: Thiol-ene "click reactions" as a promising approach to polymer materials Article Accepted Version Kazybayeva, D. S., Irmukhametova, G. S. and Khutoryanskiy, V. V. ( 2021) Thiol-ene "click reactions" as a promising approach to polymer materials. Polymer Science, Series B.

Cited by 14 publications

References 148 publications

Structural and Transport Properties of Norbornene-Functionalized Poly(vinyl alcohol) “Click” Hydrogel: A Molecular Dynamics Study

Structural and Transport Properties of Norbornene-Functionalized Poly(vinyl alcohol) “Click” Hydrogel: A Molecular Dynamics Study

Synthesis of a renewable polyamine from canola oil by photocatalyzed thiol‐ene addition of cysteamine under green conditions

Bottom‐Up Synthesized Glucan Materials: Opportunities from Applied Biocatalysis

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