Synthesis of Dibenzhydryl and Dibenzyl Penta- and Hexasulfides

Tsurugi, Jitsuo; Nakabayashi, Takeshige

doi:10.1021/jo01088a019

Cited by 29 publications

(16 citation statements)

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“…The peak wavelength (λ, in nm) increases as we move from PDS to PHS. 31 The plot of peak wavelength as a function of square root of polysulfide order (n, i.e. number of sulfur atoms) shown in inset Figure 2b follows a linear trend as expected of phenyl polysulfide thus validating the order of the synthesized polysulfides.…”

Section: Resultssupporting

confidence: 61%

A Class of Organopolysulfides As Liquid Cathode Materials for High-Energy-Density Lithium Batteries

Bhargav

Bell

Karty

et al. 2018

ACS Appl. Mater. Interfaces

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Sulfur-based cathodes are promising to enable high-energy-density lithium-sulfur batteries; however, elemental sulfur as active material faces several challenges, including undesirable volume change (∼80%) when completely reduced and high dependence on liquid electrolyte wherein an electrolyte/sulfur ratio >10 μL mg is required for high material utilization. These limit the attainable energy densities of these batteries. Herein, we introduce a new class of phenyl polysulfides CHS CH (4 ≤ x ≤ 6) as liquid cathode materials synthesized in a facile and scalable route to mitigate these setbacks. These polysulfides possess sufficiently high theoretical specific capacities, specific energies, and energy densities. Spectroscopic techniques verify their chemical composition and computation shows that the volume change when reduced is about 37%. Lithium half-cell testing shows that phenyl hexasulfide (CHSCH) can provide a specific capacity of 650 mAh g and capacity retention of 80% through 500 cycles at 1 C rate along with superlative performance up to 10 C. Furthermore, 1302 Wh kg and 1720 Wh L are achievable at a low electrolyte/active material ratio, i.e., 3 μL mg. This work adds new members to the cathode family for Li-S batteries, reduces the gap between the theoretical and practical energy densities of batteries, and provides a new direction for the development of alternative high-capacity cathode materials.

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Section: Resultssupporting

confidence: 61%

A Class of Organopolysulfides As Liquid Cathode Materials for High-Energy-Density Lithium Batteries

Bhargav

Bell

Karty

et al. 2018

ACS Appl. Mater. Interfaces

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“…[33] Both benzylpersulfide (BnSSH)[34] and adamantylpersulfide (AdSSH)[35] have been reported previously, but we report modified synthetic procedures and complete characterization data below. Thioacetic acid, acetyl chloride, sulfuryl chloride and the required thiols were purchased from commercial suppliers and used as received.…”

Section: Methodsmentioning

confidence: 99%

Reactions of isolated persulfides provide insights into the interplay between H2S and persulfide reactivity

Bailey

Pluth

2015

Free Radical Biology and Medicine

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Hydrogen sulfide is ubiquitous in biological systems and exerts function over a wide range of important physiological processes. Complementing free H2S, the reductant-labile sulfur pool plays significant roles in the translocation and action of sulfide, however the chemistry of reductant-labile sources of sulfide have not been studied systematically. Using a combination of NMR and UV-Vis spectroscopy, we investigated the spectroscopic properties and reactivity of three isolated organic persulfides and report a simple model for persulfide reactivity, including their roles as nucleophiles, electrophiles, and sulfide donors.

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“…Note that these exchange reactions may serve not only to generate crosslinks but also to alter the rank of bis‐PMN‐allylic polysulfides. A third possible crosslinking mechanism involves the oxidation of hydropersulfides by persulfenyl bromides to generate 4 and HBr 28, 29. The latter would be subsequently scavenged by epoxide.…”

Section: Discussionmentioning

confidence: 99%

Sulfuration and reversion reactions of brominated poly(isobutylene‐co‐isoprene)

Parent

White

Thom

et al. 2003

J. Polym. Sci. A Polym. Chem.

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The sulfuration and reversion products of brominated poly(isobutylene-coisoprene) (BIIR) were characterized through the use of a model compound, brominated 2,2,4,8,8-pentamethyl-4-nonene (BPMN). The reaction of BPMN with S 8 produced bisallylic polysulfides of various ranks, yielding sulfur bromide intermediates that likely contributed to the rapid oxidation of allylic sulfides into thiophenes. Reductive cure reversion to pentamethylnonene was also observed in the latter stages of vulcanization. The reaction of 2,2Ј-dithiobisbenzothiazole with BIIR and BPMN produced a stable adduct that reduced the concentration of allylic bromide available for vulcanization.

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Synthesis of Dibenzhydryl and Dibenzyl Penta- and Hexasulfides

Cited by 29 publications

References 0 publications

A Class of Organopolysulfides As Liquid Cathode Materials for High-Energy-Density Lithium Batteries

A Class of Organopolysulfides As Liquid Cathode Materials for High-Energy-Density Lithium Batteries

Reactions of isolated persulfides provide insights into the interplay between H2S and persulfide reactivity

Sulfuration and reversion reactions of brominated poly(isobutylene‐co‐isoprene)

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