Sulfur Compounds

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Organosulfur compounds (OSCs), also called organic sulfur compound, a subclass of organic substances that contain sulfur and known for their varied occurrence and unusual properties. According to the sulfur-containing functional groups, OSCs can be classified as thioethers, thioesters, thioacetals, thiols, disulfides, sulfuranes, persulfuranes, etc. Due to the presence of important linkages such as C-S bonds and C=S bonds, OSCs were widely used in organic synthesis, pharmaceutical industry, material chemistry and other fields.

Applications of Sulfur Compounds

  • Medicinal Chemistry

OSCs are essential for life which can be derived from both plant and animal sources. OSCs can serve not only as direct antioxidant-trapping electrons, but also have nonantioxidant effects such as antiplatelet, fibrinolytic, antiinflammatory, immunomodulatory, and antiaging actions. These properties of OSCs are useful in the prophylaxis and treatment of various pathological states, like cardiovascular diseases, cancer, neurodegenerative disorders, and diabetes; they have antibacterial, antiviral, and other activities. For example, as Figure 1, diallyl disulfide (DADS), a major component of garlic oil, is an inhibitor of tumorigenesis by various metabolically activated carcinogens. Allyl sulfide (AS), another OSC found in garlic, caused the reversal of hypermethylation of the RARβ2 promoter in SiHa cervical cancer cells. Dutt et al. found that S-allyl-L-cysteine (SAC) can improve skeletal muscle atrophy, and the key to its improvement lies in the regulation of the expression of certain pro-inflammatory factors. Shehatou et al. discovered that sulforaphane (SFN) could effectively reduce the levels of total cholesterol (TC) and low-density lipoprotein (LDL) in the serum of hypercholesterolemic rabbits, while significantly increasing the level of high-density lipoprotein.

(a) DADS, (b) AS, (c) SAC, (d) SFNFigure 1. (a) DADS, (b) AS, (c) SAC, (d) SFN.

  • Active Materials

On the other hand, as a class of active materials with reversible redox reactions, OSCs have great development prospects and potential for application in flow batteries due to their low price and numerous derivatives. Prof. Yu reported a novel OSCs molecule based on two-electron transfer reaction with disulfide bond (-S-S-) as the reversible redox active center for high-capacity non-aqueous flow batteries. As shown in Figure 2, OSCs can also be useful additives in electrolytes to improve the performance of sulfur cathodes and metallic lithium anodes.

(a) DMDS as an additive in  electrolyte, which changes the reduction route for the sulfur cathode [8,9]. (b)  Organosulfide as a component to form a SEI layer on lithium metal anode Figure 2. (a) DMDS as an additive in electrolyte, which changes the reduction route for the sulfur cathode [8,9]. (b) Organosulfide as a component to form a SEI layer on lithium metal anode [10].

  • Nanomaterials

As for nanomaterials, the ligands of OSCs were grafted on metal supports, thus providing conditions for surface functionalization of electronic devices or sensors. Liu et al. synthesized high-capacity noble metal single-atom catalysts based on metal-organic sulfide (MOS) framework by mimicking metalloenzyme multicenter metal-sulfur clusters. In addition, OSCs were also used in pesticides, dyes, rubber and other fields.

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References

  1. Chen, S. et al. Functional Organosulfide Electrolyte Promotes an Alternate Reaction Pathway to Achieve High Performance in Lithium-Sulfur Batteries. Angew. Chem., Int. Ed. 2016, 55: 4231-4235.
  2. Chen, S. et al. High capacity of lithium-sulfur batteries at low electrolyte/sulfur ratio enabled by an organosulfide containing electrolyte. Nano Energy. 2017, 31: 418-423.
  3. Li, G.et al. Organosulfide-plasticized solid-electrolyte interphase layer enables stable lithium metal anodes for long-cycle lithium-sulfur batteries. Nat. Commun. 2017, 8: 850.

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