Trifluoromethane Sulfonamide Research Articles

Efficacy of the chemical trifluoromethanesulfonamide as a male gametocide in field-grown sorghum [Sorghum bicolor (L.) Moench

Sorghum bicolor (L. Moench) is a cereal grain and forage crop that is grown across tropical and temperate regions of the world. Sorghum has a complete flower, resulting in self-pollination as the primary form of reproduction, but it is also grown commercially as a hybrid. Consequently, methods of cross-pollination for both breeding and hybrid seed production are important. In sorghum breeding, current methods of cross-pollination are effective, but they have limitations in terms of achieving complete and temporal male sterility. With the development of new breeding approaches, such as doubled haploids, temporal male sterility is essential. Temporal male sterility would also be useful in testing new seed parent lines prior to an investment in sterilization of the line in the cytoplasmic male sterility system. The objective of this study was to evaluate the efficacy of trifluoromethanesulfonamide (TFMSA) as a sorghum male gametocide under field conditions. TFMSA was foliarly applied to three male-fertile parental lines, in two environments, using a pipette and a sprayer, respectively, in dosages ranging from 5 to 30 mg/plant. Repeated applications over time for the 10 and 15 mg dosage rates were conducted on a subset of individual plants. The results indicate that once a minimum dosage threshold (between 10 and 15 mg) was reached, panicles became male sterile. Additional dosages and number of applications had little overall effect, and both hand-applied and sprayer-applied TFMSA had similar male sterility induction capability. From these studies, it appears that TFMSA can be used as an effective chemical male gametocide on sorghum under field conditions.

Male sterility induction of sorghum using chemical hybridizing agent TFMSA, trifluoromethanesulfonamide

In sorghum, male sterility has been induced mainly using mechanical and genetic means with minimal use of chemical methods. Mechanical sterility induction is limited to producing small quantities of seed and genetic male sterility is limited to specific germplasm. An effective chemical hybridizing agent could be used to produce large amounts of seed and would not be limited by genotypes. The chemical trifluoromethanesulfonamide (TFMSA) was evaluated as a male gametocide in sorghum. In greenhouse conditions, TFMSA induced varying degrees of male sterility contingent on the dosage, timing of application, and sorghum genotype. If applied at or after the flag leaf emergence, panicles were male fertile but male sterile when applied at least 2 d before the flag leaf emerged. In terms of dosage, 2 mg of TFMSA rendered a BTx623 male sterile if applied 2–6 d prior to flag leaf emergence. However, 30 mg of TFMSA applied as much as 34 d before the flag leaf emerged also induced complete sterility of the panicle. There may be a genotypic effect as less TFMSA was necessary to induce complete male sterility in BTx623 than in BTxArg-1. No phytotoxic effects or reductions in female fertility were observed in dosages of TFMSA up to 40 mg. Germination of hybrid seed made on treated plants was equal to that of the parents and the hybrid seedlings were phenotypically normal. The results indicate that male sterility can be induced effectively in sorghum using TFMSA at appropriate dosages and application timings.

Is carbonic anhydrase activity of photosystem II required for its maximum electron transport rate?

It is known, that the multi-subunit complex of photosystem II (PSII) and some of its single proteins exhibit carbonic anhydrase activity. Previously, we have shown that PSII depletion of HCO3−/CO2 as well as the suppression of carbonic anhydrase activity of PSII by a known inhibitor of α‑carbonic anhydrases, acetazolamide (AZM), was accompanied by a decrease of electron transport rate on the PSII donor side. It was concluded that carbonic anhydrase activity was required for maximum photosynthetic activity of PSII but it was not excluded that AZM may have two independent mechanisms of action on PSII: specific and nonspecific. To investigate directly the specific influence of carbonic anhydrase inhibition on the photosynthetic activity in PSII we used another known inhibitor of α‑carbonic anhydrase, trifluoromethanesulfonamide (TFMSA), which molecular structure and physicochemical properties are quite different from those of AZM. In this work, we show for the first time that TFMSA inhibits PSII carbonic anhydrase activity and decreases rates of both the photo-induced changes of chlorophyll fluorescence yield and the photosynthetic oxygen evolution. The inhibitory effect of TFMSA on PSII photosynthetic activity was revealed only in the medium depleted of HCO3−/CO2. Addition of exogenous HCO3− or PSII electron donors led to disappearance of the TFMSA inhibitory effect on the electron transport in PSII, indicating that TFMSA inhibition site was located on the PSII donor side. These results show the specificity of TFMSA action on carbonic anhydrase and photosynthetic activities of PSII. In this work, we discuss the necessity of carbonic anhydrase activity for the maximum effectiveness of electron transport on the donor side of PSII.

Computational Design of New Magnesium Electrolytes with Improved Properties

In this work, we use computational design to examine 15 new electrolyte salt anions by performing chemical variations and mutations on the bis(trifluoromethane)sulfonamide (TFSI) anion. On the basis of our calculations, we propose two new anions as potential candidates for magnesium energy-storage systems, which are evolved from TFSI with the substitution of sulfur atoms in TFSI and the modification of functional groups. The applicability of these new anion salts is examined through comprehensive calculations using both first-principles as well as benchmarked classical molecular dynamics. We elucidate the important properties of these anions, including the electrochemical stability window, chemical decomposition, preferred solvation structure, diffusion coefficient, and other dynamical properties for 15 rationally designed molecules. Two of the designed anions are found to successfully avoid the vulnerability of TFSI during ion-pair charge-transfer reactions while retaining comparable or better performanc...

Highly Stable Near-Unity Photoluminescence Yield in Monolayer MoS2 by Fluoropolymer Encapsulation and Superacid Treatment.

Recently, there has been considerable research interest in two-dimensional (2D) transition-metal dichalcogenides (TMDCs) for future optoelectronic applications. It has been shown that surface passivation with the organic nonoxidizing superacid bis(trifluoromethane)sulfonamide (TFSI) produces MoS2 and WS2 monolayers whose recombination is at the radiative limit, with a photoluminescence (PL) quantum yield (QY) of ∼100%. While the surface passivation persists under ambient conditions, exposure to conditions such as water, solvents, and low pressure found in typical semiconductor processing degrades the PL QY. Here, an encapsulation/passivation approach is demonstrated that yields near-unity PL QY in MoS2 and WS2 monolayers which are highly stable against postprocessing. The approach consists of two simple steps: encapsulation of the monolayers with an amorphous fluoropolymer and a subsequent TFSI treatment. The TFSI molecules are able to diffuse through the encapsulation layer and passivate the defect states of the monolayers. Additionally, we demonstrate that the encapsulation layer can be patterned by lithography and is compatible with subsequent fabrication processes. Therefore, our work presents a feasible route for future fabrication of highly efficient optoelectronic devices based on TMDCs.

Electrochemical Properties of Cus Cathode Material for Lithium Rechargeable Batteries Prepared By Spray Pyrolysis

Increased demand in society for the replacement of the conventional petroleum-based energy sources by renewable energy requires development of an advanced energy storage systems. Lithium-ion batteries (LIBs) are one of the most attractive options and dominate consumer market nowadays; however, they still need to be improved significantly to fulfill the requirements of the electrical grid applications, electric vehicles (EVs) and hybrid electric vehicles(HEVs) [1]. Recently, CuS is gaining attention as a prospective transition metal cathode material due to its high theoretical capacity of 560 mAh g-1 and high electronic conductivity (10-3 S cm-1). The main hindrance of CuS is the severe capacity decay coming from the dissolution of Li2S species in the electrolyte formed during reduction reaction with Li, which cause short lifetime [2]. In our approach, we prepared CuS by one-step synthesis method of spray pyrolysis. It is known that S has theoretical specific capacity of 1675 mAh g-1 with opportunity for providing a high energy density around 2500 W h kg-1 on a weight basis assuming a complete reaction with lithium [3]. Despite these advantages, Li-S batteries suffer from several issues that impede their practical applications such as high resistance and shuttle effect triggering poor cycle life and low active mass utilization [4]. we investigated improvements of the electrochemical properties of CuS. The precursor solution was prepared by dissolving accurate amount of copper (II) nitrate trihydrate (Cu (NO3)2·3H2O) and thiourea (CS (NH2)2) in distilled water with different Cu/S molar ratios, which was sprayed inside a laminar flow reactor using an ultrasonic nebulizer. The resulting samples were characterized by X-ray diffraction (XRD), Fourier transform infrared spectroscopy (FTIR), scanning electron microscopy (FE-SEM), auger electron spectroscopy (AES) and inductively coupled plasma-optical emission spectroscopy (ICP-OES) to study their physical properties, such as crystal structure, chemical composition, surface and interior morphologies. Furthermore, their electrochemical properties have been investigated using CR2032 coint-type cells. The cathode electrode was prepared by mixing as-prepared CuS, polyvinylidene fluoride (PVdF) and acetylene black (AB) in the 80:10:10 wt. % ratio. The coin-type cells were assembled with 1 M lithium bis(trifluoromethane sulfonamide)(LiTFSI) in 1:1 w/w in 1,3-dioxolane (DOL)/ dimethoxyethane (DME) electrolyte and lithium metal foil used as a reference electrode in an argon-filled glove box (99.9995% purity). The cell testing was performed in the voltage range between 1.0-3.0 V and 1C was used as 560 mA g-1. The as-prepared CuS sample exhibited promising results with stable capacity retention up to 100 cycles at 1C rate. The mechanism associated with the improved electrochemical performance will be discussed in the presentation.

Plasticized Polymer Composite Single-Ion Conductors for Lithium Batteries.

Lithium bis(trifluoromethane) sulfonamide (TFSI) is a promising electrolyte salt in lithium batteries, due to its good conductivity and high dissociation between the lithium cation and its anion. By tethering N-pentane trifluoromethane sulfonamide (C5NHTf), a TFSI analogue molecule, onto the surface of silica nanoparticle as a monolayer coverage should increase the Li(+) transference number to unity since anions bound to particles have reduced mobilities. Silica polymer composite has better mechanical property than that of the pure PEO. Analogously trifluoromethane sulfonic aminoethyl methacrylate (TfMA), a TFSI analogue vinyl monomer, was polymerized on silica nanoparticle surface as a multilayer coverage. Anchored polyelectrolytes to particle surfaces offer multiple sites for anions, and in principle the carrier concentration would increase arbitrarily and approach the carrier concentration of the bulk polyelectrolyte. Monolayer grafted nanoparticles have a lithium content of 1.2 × 10(-3) g Li/g, and multilayer grafted nanoparticles have a lithium content over an order higher at 2 × 10(-2) g Li/g. Electrolytes made from monolayer grafted particles exhibit a weak conductivity dependence on temperature, exhibiting an ionic conductivity in the range of 10(-6) S/cm when temperatures increase to 80 °C. While electrolytes made from multilayer grafted particles show a steep increase in conductivity with temperature with an ionic conductivity increase to 3 × 10(-5) S/cm at 80 °C, with an O/Li ratio of 32.

Multi-Wall Carbon Nanotubes As Cathodes for Lithium-Air Batteries: Effect of Catalysts and Additives

Batteries with high specific energy densities have attracted a lot of attention due to their demand in electric vehicles (EVs). Due to the increase in demand for energy storage devices for applications such as load-levelling of electrical energy supply and demand [1], propulsion for electric vehicles, and microelectro-mechanical devices, the research for new classes of electrode materials that provide high energy, high power and cycle life longer than lithium-ion batteries is being motivated [2,3]. Lithium air batteries have high specific energy density and they can achieve four times higher energy density than the current lithium ion batteries [2, 3]. Lithium air batteries also have higher theoretical energy density than lithium ion batteries [4]. Catalysts have been shown to improve both the battery capacity and the recyclability of these batteries when used in cathodes. Several catalysts have been discovered for lithium air batteries. Debart et al. used several catalysts for lithium oxygen batteries with non-aqueous electrolyte. The electro-catalysts used by them included Pt, La0.8Sr0.2MnO3, Fe2O3, NiO, CuO, CoFe2O4. Co3O4 exhibited highest discharge capacity and best cycling performance. Later Debart et al. examined manganese oxides as catalysts for lithium oxygen batteries. Mn3O4, bulk Mn2O3, bulk α, β, λ, γ-MnO2, α-MnO2 nanowires and β-MnO2 nanowires were used as catalysts [6]. The air cathode with α-MnO2 as the catalyst showed the highest capacity of about 3000 mAh/g (carbon) Lu et al. reported ORR studies on polycrystalline metal catalysts of palladium, platinum, ruthenium, gold and glassy carbon surfaces in non-aqueous electrolyte [5]. In this study, we investigate various modes of loading palladium-based catalysts and their effect on the capacity and round-trip efficiency of lithium-air batteries. The aim of our study is to increase the first discharge capacity, improve the recyclability, increase capacity retention and improve the recyclability of the battery. The loading and morphology the catalyst-CNT cathodes were studied using transmission electron microscopy. Electrochemical testing using electrochemical impedance spectroscopy and charge-discharge cycling were also investigated. The cathode consisted of conductive carbon cloth coated with MWCNT or palladium inside MWCNT. Celgard 2040 was used as a separator. LiTFSi (Bis Trifluoromethane sulfonamide Lithium salt) in TEGDME (Tetraethyl glycol di-methyl ether) was used as electrolyte. The battery was assembled in the Swagelok cell. Figure 1 shows the assembly of the battery. Figure 2 shows the TEM images of palladium nanoparticles inside MWCNT. Figure 3 shows Pristine CNT with first cycle at a current rate of 200 mA/g showing a discharge capacity of 9300 mAh/g and a charge capacity of 8250 mAh/g. Figure 4 shows catalyst-loaded CNT with first cycle at a current rate of 200 mA/g showing a discharge capacity of 13800 mAh/g and a charge capacity of 3000 mAh/g.

A new route to the syntheses of N-(fluorosulfuryl)sulfonamide salts: Crystal structure of Ph 4P + [CF 3SO 2NSO 2F] −

A new route for the preparation of potassium and tetraphenylphosphonium salts of N-(fluorosulfuryl)trifluoromethane sulfonamide is described. N-(chlorosulfuryl)-trifluoromethane sulfonamide CF 3SO 2–NH–SO 2Cl, that was used for preparations of both salts, was prepared by the reaction of trifluoromethane sulfonamide CF 3SO 2NH 2 and chlorosulfonic acid in the presence of SOCl 2. The obtained N-(chlorosulfuryl)trifluoromethane sulfonamide was converted to potassium N-(fluorosulfuryl)trifluoromethane sulfonamide by using anhydrous KF. Potassium N-(fluorosulfuryl)trifluoromethane sulfonamide served as a starting material for the preparation of the corresponding tetraphenylphosphonium N-(fluorosulfuryl)trifluoromethane sulfonamide that crystallizes from the aqueous solution of potassium N-(fluorosulfuryl)trifluoromethane sulfonamide and tetraphenylphosphonium chloride. N-(fluorosulfuryl)trifluoromethane sulfonamide tetraphenylphosphonium salt is tetragonal, space group P 4 ¯ .

Design, synthesis and evaluation of trifluoromethane sulfonamide derivatives as new potent and selective peroxisome proliferator-activated receptor α agonists

Starting from the structure of 5, a two-step strategy was applied to identify a new generation of trifluoromethane sulfonamides as potent PPARα agonists. Synthesis, in vitro and in vivo evaluation of the most potent compound are reported.

Localization of carbonic anhydrase in living osteoclasts with bodipy 558/568-modified acetazolamide, a thiadiazole carbonic anhydrase inhibitor.

We describe the synthesis of Bodipy 558/568-modified acetazolamide, a fluorescent inhibitor of carbonic anhydrase and its use to localize the enzyme in living cells. The modified acetazolamide, with its specific sulfonamide group intact, labeled cells at concentrations as low as 10(-9) M, with a minimal loading time of 5 min. The staining was decreased by 57.4% by preincubating cells with unaltered acetazolamide (1:100) or with trifluoromethane sulfonamide, 6-ethoxyzolamide, and 5-(3-hydroxybenzoyl)-thiophene-2-sulfonamide. The efficacy of the inhibitor was unchanged by the fluorescent label, as determined by an acridine orange assay that detects acidification of osteoclasts, the cell model used in this study. This compound should prove to be useful for studying carbonic anhydrase in many organisms because of the high degree of conservation of the active site of this enzyme. (J Histochem Cytochem 47:545-550, 1999)