Thiol-X chemistry in polymer science

Schlaad, Helmut

doi:10.1016/j.polymer.2014.09.020

Cited by 10 publications

(7 citation statements)

References 25 publications

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“…Indeed, thiols are very reactive molecules, used either as strongly nucleophilic thiolate anion, or as electrophilic thiyl radical. As a consequence, a broad variety of substrates is accessible for reaction [22,23], which could all be gathered in a toolbox of available thiol-X reactions ( 1) [24,25]. M a n u s c r i p t 3 It should be noted that although efficient transformations involving thiols have risen to an unprecedented level of popularity during the last years, thiol chemistry has always been important in macromolecular synthesis.…”

Section: Introductionmentioning

confidence: 99%

Protected thiol strategies in macromolecular design

Goethals

Frank

Prez

2017

Progress in Polymer Science

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Section: Introductionmentioning

confidence: 99%

Protected thiol strategies in macromolecular design

Goethals

Frank

Prez

2017

Progress in Polymer Science

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“…Although the earliest example dates back as early as more than a century ago, thiol based chemistries have recently been revitalized in polymer and materials science since they provide simple and versatile tool for various applications including polymer/network synthesis and efficient coupling chemistry in post-polymerization modifications [42][43][44].…”

Section: Introductionmentioning

confidence: 99%

Thiol reactive polybenzoxazine precursors: A novel route to functional polymers by thiol-oxazine chemistry

Semerci

Kışkan

Yaǧcı

2015

European Polymer Journal

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“…25,26 Thiol-X reactions include thiol-ene, thiol-yne, thiol-isocyanate, thiol-halogen, thiolepoxide and thiol-disulfide reactions. Over the past few years, chemical reactions based on thiols, also called thiol-X reactions, have found wide applications in polymer synthesis, polymer modifications and preparation of bio-conjugates.…”

Section: Introductionmentioning

confidence: 99%

“…Over the past few years, chemical reactions based on thiols, also called thiol-X reactions, have found wide applications in polymer synthesis, polymer modifications and preparation of bio-conjugates. 25,26 Thiol-X reactions include thiol-ene, thiol-yne, thiol-isocyanate, thiol-halogen, thiolepoxide and thiol-disulfide reactions. Among the thiol-X reactions, the exchange reaction between thiols and PDS groups 27 can be conducted at room temperature with high efficiency, and this reaction was used in surface modification 28 and the synthesis of polymer-peptide conjugates.…”

Section: Introductionmentioning

confidence: 99%

Reductant-triggered rapid self-gelation and biological functionalization of hydrogels

Chen

Wu²,

Cheng³

et al. 2015

Polym. Chem.

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Hydrogels have found wide applications in many fields. Although plenty of mature preparation methodologies are available now, there is certainly a continuous impetus in developing new methods toward simplicity, adjustability and satisfying diverse emerging needs. In this paper, a novel and efficient approach for hydrogel preparation is proposed. Polyacrylamide (PAM) chains with pyridyl disulfide (PDS) side groups were synthesized by free-radical polymerization. Upon addition of a tiny amount of reductants to the aqueous solution of the synthesized copolymer, part of the PDS groups are reduced to free thiols, and the subsequent exchange reaction between thiol groups and PDS results in disulfide-crosslinked hydrogels. The rapid self-gelation process was monitored by in situ rheological measurements, and the network structures of the hydrogels were observed using a scanning electron microscope. It has been found that the mechanical properties and pore sizes of the hydrogels could be tuned by changing the polymer concentration and the amounts of the reductants added into the solution. The residual PDS groups in the hydrogels provide reaction sites for immobilization of biological functional molecules.Reduced glutathione and bovine serum albumin were successfully immobilized in the hydrogels, and the bioactivities of the hydrogels were measured in this research. The disulfide crosslinks are cleavable and the hydrogels are dissociated under reducing conditions, which indicates that the hydrogels may find potential applications in biological and medical fields.Scheme 1 (a) Chemical reactions in the process of the reductanttriggered self-gelation; (b) illustration of the self-gelation and post-functionalization process. PaperPolymer ChemistryPolym. Chem. This journal is

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Thiol-X chemistry in polymer science

Cited by 10 publications

References 25 publications

Protected thiol strategies in macromolecular design

Protected thiol strategies in macromolecular design

Thiol reactive polybenzoxazine precursors: A novel route to functional polymers by thiol-oxazine chemistry

Reductant-triggered rapid self-gelation and biological functionalization of hydrogels

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