Redox Cleavage of S—S Linkage in Diaryl and Cyclic Alkyl Disulphides

Wang, Chi-Hua

doi:10.1038/203075a0

Cited by 12 publications

(5 citation statements)

References 5 publications

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“…[53] One of the attractive properties of thioctic acid is its ability to form linear poly(thioctic acid) through thermally initiated ring-opening polymerization (ROP) of the five-membered ring containing disulfide bonds. [54][55] Disulfide bonds show dynamic behavior, which endows poly(thioctic acid) materials with excellent self-repairing properties. However, the linear poly(thioctic acid) tends to depolymerize and revert to its crystalline thioctic acid monomer at room temperature due to the rapid dissociation of disulfide bonds.…”

Section: Resultsmentioning

confidence: 99%

“…Reasonably, acetylacetonate metal complexes have been widely used as the catalysts of ROP of thioctic acid and the dynamic transesterification process. [55,63] Specifically, cyclic disulfides undergo an electron transfer process catalyzed by zinc acetylacetonate (ZnAA) to achieve ring-opening reactions and create thiyl radicals, followed by the further formation of linear PTAs. ZnAA also catalyzes the reaction of epoxy with anhydride/carboxylic acid and dynamic transesterification.…”

Section: Resultsmentioning

confidence: 99%

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Covalent Adaptable Networks with Dual Dynamic Covalent Bonds for Self‐Repairing Infrared Transmitting Materials

Cui,

Wang,

Chen

et al. 2024

Adv Funct Materials

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Infrared transmitting materials (IRTMs) are prone to mechanical and corrosion damage during long‐time exposure to harsh outside environments. However, conventional IRTMs frequently lack self‐repairability that limit their lifespan. To address the limitation, thioctic acid‐based epoxy resins (TAEs) are developed from natural thioctic acid and commercial epoxy monomers. The double ring‐opening polymerization (ROP) reactions of thioctic acid and epoxy groups result in dual dynamic covalent bonds with varying bond energies containing relatively weak disulfide bonds and strong ester bonds. As compared with conventional covalent adaptable networks (CANs) that present rapid creep properties when heated, TAEs maintain their geometric stability during rapid self‐repairing at a mild temperature of 80 °C by enhancing network integrity through stable ester crosslinking points. The feature renders TAEs self‐repairing capability while maintaining precise geometrical dimensions, which is suitable for infrared transmitting devices. On the other hand, TAEs exhibit high near‐infrared transmittance (>80%). Therefore, TAEs with self‐repairability and high infrared transmittance demonstrate they can be used as superior polymeric IRTM.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Covalent Adaptable Networks with Dual Dynamic Covalent Bonds for Self‐Repairing Infrared Transmitting Materials

Cui,

Wang,

Chen

et al. 2024

Adv Funct Materials

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“…An excellent account of enyne cyclization by Taniguchi et al builds upon work published forty years previous by Wang [99], in which the disulfide bond of diphenyl disulfide was cleaved by dimethylaniline to yield polymers via reaction with a suitable nitrile species. This original reaction was postulated to initiate by single-electron transfer (SET) from the amine.…”

Section: Modern Approachesmentioning

confidence: 99%

Thiyl Radicals: Versatile Reactive Intermediates for Cyclization of Unsaturated Substrates

Lynch

Scanlan

2020

Molecules

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Sulfur centered radicals are widely employed in chemical synthesis, in particular for alkene and alkyne hydrothiolation towards thioether bioconjugates. The steadfast radical chain process that enables efficient hydrothiolation has been explored in the context of cascade reactions to furnish complex molecular architectures. The use of thiyl radicals offers a much cheaper and less toxic alternative to the archetypal organotin-based radical methods. This review outlines the development of thiyl radicals as reactive intermediates for initiating carbocyclization cascades. Key developments in cascade cyclization methodology are presented and applications for natural product synthesis are discussed. The review provides a chronological account of the field, beginning in the early seventies up to very recent examples; a span of almost 50 years.

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“…As shown in DSC and XRD, the lower crystallinity in RS/XT-GCSPHs was observed, showing that a considerable incensement in amorphous regions occurred. As a consequence, based on the previously reports, [23][24][25] deconvoluted ATR-FTIR spectra was employed to ascertain those amorphous regions and ordered structures. And the ratio of absorbance 1045/1022 and 1022/ 995 cm À1 can be used as a measure of the amount of ordered starch to amorphous starch and the state of organization of the double helices localized inside crystallites, respectively.…”

Section: Crystalline Structures and Amorphous Regions And Ordered Strmentioning

confidence: 99%

“…According to Fu et al, Wang et al, and Dias et al, [19,28,29] the retrogradation of starch gel result in the loss of water content, especially higher mobility water. Therefore, as reported in previous literatures, [17,19,24,28] the T 2i relaxation time determined by LF-NMR with a sequence of CPMG is often applied to evaluate the diverse mobility and microscopic distributions of the various fractions of water in starch gels. The smaller the T 2i is, the weaker the mobility of the corresponding water is.…”

Section: Water Distribution In Starch Gelsmentioning

confidence: 99%

Effect of Grass Carp Skin Protein Hydrolysates on the Retrogradation Tendency of Gelatinized Rice Starch in the Presence of Non‐Ionic and Ionic Hydrocolloids During Cold Storage

et al. 2019

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Gluten‐free (GF) goods produced from rice starch (RS) are the most preferred products for consumers with celiac disease. But these foods lack essential amino acids and are prone to retrogradation, which are the barriers related to rice starch‐containing GF foods. The objective of this work is to study the synergistic impact of grass carp skin protein hydrolysates (GCSPHs) in the presence of xanthan (XT) and guar gum (GG) on the retrogradation tendency of gelatinized rice starch (GRS). During 14‐day storage at 4 °C, texture profile analysis revealed that combined GCSPHs and XT can significantly reduce the hardness from 1181.8 to 249.3 g, which has a more suppressive effect on retrogradation than that of all the other gel samples. The physical phenomena underlying the reduced retrogradation of GRS based on differential scanning calorimetry, X‐ray diffraction, attenuated total reflectance fourier transform infrared, low‐field 1H nuclear magnetic resonance, and scanning electron microscopy are characterized and it is shown that GCSPHs in GRS/XT gel can remarkably decrease the double helices localized inside crystallites of retrogradation, increase the amorphous region, immobilize the transversal relaxation time, lock the water in the GRS system and form a more homogeneous continuous phase, which can play a significant role in mitigating the retrogradation of GRS. These findings suggest that the synergism of GCSPHs and anionic hydrocolloids (XT) is more effective for inhibiting the retrogradation of GRS and improving the quality and nutrition of RS‐containing GF foods.

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Redox Cleavage of S—S Linkage in Diaryl and Cyclic Alkyl Disulphides

Cited by 12 publications

References 5 publications

Covalent Adaptable Networks with Dual Dynamic Covalent Bonds for Self‐Repairing Infrared Transmitting Materials

Covalent Adaptable Networks with Dual Dynamic Covalent Bonds for Self‐Repairing Infrared Transmitting Materials

Thiyl Radicals: Versatile Reactive Intermediates for Cyclization of Unsaturated Substrates

Effect of Grass Carp Skin Protein Hydrolysates on the Retrogradation Tendency of Gelatinized Rice Starch in the Presence of Non‐Ionic and Ionic Hydrocolloids During Cold Storage

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