Anionic Copolymerization of Styrene Sulfide with Elemental Sulfur (S8)

Wręczycki, Jakub; Bieliński, Dariusz M.; Kozanecki, Marcin; Maczugowska, Paulina; Mlostoń, Grzegorz

doi:10.3390/ma13112597

Cited by 27 publications

(21 citation statements)

References 42 publications

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“…Poly(styrene-alt-sulphur), from S8/styrene sulphide ROCOP, showed that increasing the sulphur content (although not quantified) decreased the Tg from 58 to 43 °C which matched previous reports that increasing the sulphur wt% reduced brittleness. [203] It is emphasised that sulphur-sulphur bonds are often dynamic, a property exploited in autonomously self-healing polyurethane elastomers where macroscopic damage was healed through dynamic disulphides. [204] By simply bringing two ends of the cut specimen bar into contact mechanical properties were nearly completely restored after 24 h. In future, these ROCOP polymers should be explored as self-healing materials.…”

Section: Accepted Manuscriptmentioning

confidence: 99%

Heterocycle/Heteroallene Ring‐Opening Copolymerization: Selective Catalysis Delivering Alternating Copolymers

2021

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Heteroatom‐containing polymers have strong potential as sustainable replacements for petrochemicals, show controllable monomer–polymer equilibria and properties spanning plastics, elastomers, fibres, resins, foams, coatings, adhesives, and self‐assembled nanostructures. Their current and future applications span packaging, house‐hold goods, clothing, automotive components, electronics, optical materials, sensors, and medical products. An interesting route to these polymers is the catalysed ring‐opening copolymerisation (ROCOP) of heterocycles and heteroallenes. It is a living polymerization, occurs with high atom economy, and creates precise, new polymer structures inaccessible by traditional methods. In the last decade there has been a renaissance in research and increasing examples of commercial products made using ROCOP. It is better known in the production of polycarbonates and polyesters, but is also a powerful route to make N‐, S‐, and other heteroatom‐containing polymers, including polyamides, polycarbamates, and polythioesters. This Review presents an overview of the different catalysts, monomer combinations, and polymer classes that can be accessed by heterocycle/heteroallene ROCOP.

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Section: Accepted Manuscriptmentioning

confidence: 99%

Heterocycle/Heteroallene Ring‐Opening Copolymerization: Selective Catalysis Delivering Alternating Copolymers

2021

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“…The Absorption band at 988 cm −1 was ascribed to the saccharide structure of chitosan [16] . A new band appeared at 657 cm −1 this band can be assigned to the stretching vibration of the C–S bond and this constitutes a successful synthesis of chitosan-SNPs formulation [21] . Figure 6 shows FTIR spectra of PEG-SNPs in which the absorption bands in the region 3450–3200 cm −1 with a peak at 3424.95 cm −1 were assigned to -OH stretching vibrations.…”

Section: Resultsmentioning

confidence: 74%

Antimicrobial activities encountered by sulfur nanoparticles combating Staphylococcal species harboring scc<i>mec</i>A recovered from acne vulgaris

et al. 2021

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<abstract> <p>Over decades, sulfur has been employed for treatment of many dermatological diseases, several skin and soft tissue, and <italic>Staphylococcus</italic> infections. Because of its abuse, resistant bacterial strains have emerged. Nanotechnology has presented a new horizon to overcome abundant problems including drug resistance. Nano-sized sulfur has proven to retain bactericidal activity. Consequently, the specific aims of this study are exclusively directed to produce various sulfur nanoparticles formulations with control of particle size and morphology and investigate the antibacterial activity response specifically classified by the category of responses of different formulations, for the treatment of acne vulgaris resistant to conventional antibiotics. In this study, we produced uncoated sulfur nanoparticles (SNPs), sulfur nano-composite with chitosan (CS-SNPs), and sulfur nanoparticles coated with polyethylene glycol (PEG-SNPs) and evaluate their bactericidal impact against <italic>Staphylococcus aureus</italic> and <italic>Staphylococcus epidermidis</italic> isolated from 173 patients clinically diagnosed acne vulgaris. Accompanied with molecular investigations of <italic>erm</italic>B and <italic>mec</italic>A resistance genes distribution among the isolates. Sulfur nanoparticles were synthesized using acid precipitation method and were characterized by scanning electron microscope (SEM), transmission electron microscopy (TEM), energy dispersed x-ray spectroscopy (EDX), and Fourier transform infrared spectroscopy (FTIR). Moreover, agar diffusion and broth micro-dilution methods were applied to determine their antibacterial activity and their minimum inhibitory concentration. PCR analysis for virulence factors detection. Results: TEM analysis showed particle size of SNPs (11.7 nm), PEG-SNPs (27 nm) and CS-SNPs (33 nm). Significant antibacterial activity from nanoparticles formulations in 100% dimethyl sulfoxide (DMSO) with inhibition zone 30 mm and MIC at 5.5 µg/mL. Furthermore, the prevalence of <italic>mecA</italic> gene was the most abundant among the isolates while <italic>ermB</italic> gene was infrequent. Conclusions: sulfur nanoparticles preparations are an effective treatment for most <italic>Staphylococcus</italic> bacteria causing acne vulgaris harboring multi-drug resistance virulence factors.</p> </abstract>

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“…The developed protocols of sulfurization in the presence of fluoride anion can be of interest not only for the synthesis of sulfur-rich heterocycles, such as 1,2,4-trithiolanes [ 28 ], 1,2,4,5-tetrathianes [ 35 , 36 ] or 1,2,3,5,6-pentathiepanes, but also for the preparation of sulfur-rich polymers starting with alkyl- [ 37 , 38 ] or aryl [ 39 ] substituted thiiranes. In the present work, fluoride anion was shown to act as an alternative, nucleophilic catalyst and can replace smelly and unstable sodium (or potassium) thiophenolate in the activation of elemental sulfur in reactions with thiiranes.…”

Section: Discussionmentioning

confidence: 99%

The Fluoride Anion-Catalyzed Sulfurization of Thioketones with Elemental Sulfur Leading to Sulfur-Rich Heterocycles: First Sulfurization of Thiochalcones

et al. 2021

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Fluoride anion was demonstrated as a superior activator of elemental sulfur (S8) to perform sulfurization of thioketones leading to diverse sulfur-rich heterocycles. Due to solubility problems, reactions must be carried out either in THF using tetrabutylammonium fluoride (TBAF) or in DMF using cesium fluoride (CsF), respectively. The reactive sulfurizing reagents are in situ generated, nucleophilic fluoropolysulfide anions FS(8−x)−, which react with the C=S bond according to the carbophilic addition mode. Dithiiranes formed thereby, existing in an equilibrium with the ring-opened form (diradicals/zwitterions) are key-intermediates, which undergo either a step-wise dimerization to afford 1,2,4,5-tetrathianes or an intramolecular insertion, leading in the case of thioxo derivatives of 2,2,4,4-tetramethylcyclobutane-1,3-dione to ring enlarged products. In reactions catalyzed by TBAF, water bounded to fluoride anion via H-bridges and forming thereby its stable hydrates is involved in secondary reactions leading, e.g., in the case of 2,2,4,4-tetramethyl-3-thioxocyclobutanone to the formation of some unexpected products such as the ring enlarged dithiolactone and ring-opened dithiocarboxylate. In contrast to thioketones, the fluoride anion catalyzed sulfurization of their α,β-unsaturated analogues, i.e., thiochalcones is slow and inefficient. However, an alternative protocol with triphenylphosphine (PPh3) applied as a catalyst, offers an attractive approach to the synthesis of 3H-1,2-dithioles via 1,5-dipolar electrocyclization of the in situ-generated α,β-unsaturated thiocabonyl S-sulfides. All reactions occur under mild conditions and can be considered as attractive methods for the preparation of sulfur rich heterocycles with diverse ring-size.

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Anionic Copolymerization of Styrene Sulfide with Elemental Sulfur (S8)

Cited by 27 publications

References 42 publications

Heterocycle/Heteroallene Ring‐Opening Copolymerization: Selective Catalysis Delivering Alternating Copolymers

Heterocycle/Heteroallene Ring‐Opening Copolymerization: Selective Catalysis Delivering Alternating Copolymers

Antimicrobial activities encountered by sulfur nanoparticles combating Staphylococcal species harboring scc<i>mec</i>A recovered from acne vulgaris

The Fluoride Anion-Catalyzed Sulfurization of Thioketones with Elemental Sulfur Leading to Sulfur-Rich Heterocycles: First Sulfurization of Thiochalcones

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