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Structure of 90076-65-6
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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Ultrasoft Iontronics: Stretchable Diodes Enabled by Ionically Conductive Bottlebrush Elastomers
Wu, Xia ; Xu, Pengfei ; Zhang, Zefang ; Yang, Qi ; Huang, Xi ; Pan, Peng , et al.
Abstract: Inspired by the controlled ion migration found in biological systems, ionic diodes that regulate ion flow in iontronic systems have shown great potential for applications in human–machine interfaces, wearable, and implantable devices. However, developing biointegrable ionic diodes with mechanical compliance to biological tissues remains challenging due to the limited availability of ultrasoft materials. Although hydrogel-based diodes can achieve ultrasoftness, they suffer from dehydration, resulting in instability in mechanical and electrical performance. Here, a solvent-free, ultrasoft, and stretchable ionic diode enabled by oppositely charged bottlebrush elastomers (BBEs) is presented. The nanostructure of bottlebrush polymers allows the crosslinked BBE diode to achieve tissue-matched softness. Meanwhile, copolymerized ionic liquids ensure stable ionic conductivity by preventing leaching and thermal evaporation. The BBE diode achieves an ultralow Young’s modulus (<23 kPa), stretchability exceeding 400%, and a high rectification ratio of 46. To our knowledge, this is the softest ionic diode ever reported. Its functionality in ionic circuits is demonstrated, including full-wave rectifiers and logic gates. Furthermore, it is integrated into self-powered biointerfacing devices for strain sensing, evaluated through finger flexion, eye blinking, and stomach volume changes in an ex vivo model. These results highlight its potential for soft iontronic systems and next-generation bioelectronic interfaces.
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Keywords: bottlebrush elastomers ; ionic diode ; ionic liquids ; iontronics ; polyelectrolytes
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Nickel-Based Two-Electron Redox Shuttle for Dye-Sensitized Solar Cells in Low Light Applications
Ravinder Kaur ; Niharika Dalpati ; Jared H. Delcamp ; Byron H. Farnum ;
Abstract: Dye-sensitized solar cells (DSCs) are important to indoor solar powered devices and energy sustainable buildings because of their remarkable performance under indoor/ambient light conditions. Triiodide/iodide (I3–/I–) has been used as the most common redox mediator in DSCs because of its desirable kinetic properties and multielectron redox cycle. However, the low redox potential, corrosiveness, competitive visible light absorption, and lack of tunability of this redox mediator limit its performance in many DSC devices. Here we report a class of transition metal complex redox shuttles which operate on a similar multielectron redox cycle as I3–/I– while maintaining desirable kinetics and improving on its limitations. These complexes, nickel dithiocarbamates, were evaluated as redox shuttles in DSCs, which exhibited excellent performance under low light conditions. The recombination behavior of the redox shuttles with electrons in TiO2, dye regeneration behavior, and counter electrode electron transfer resistance were studied via chronoamperometry and electrochemical impedance spectroscopy (EIS). Further, DSC devices were studied with the Ni-based redox shuttles via incident photon-to-current conversion efficiencies (IPCEs) and current–voltage (J–V) curves under varied light intensities. The Ni-based redox shuttles showed up to 20.4% power conversion efficiency under fluorescent illumination, which was higher than I3–/I–-based devices (13%) at similar electrolyte concentrations. Taken together, these results show that nickel dithiocarbamate redox shuttles have faster rates of dye regeneration than the I3–/I– shuttle but suffer from faster recombination of photoinjected electrons with oxidized Ni(IV) species, which decrease photovoltages.
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Keywords: dye-sensitized solar cells ; nickel(IV) ; redox shuttle ; dithiocarbamate ; indoor photovoltaic
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EunBi Oh ; Alexander Q. Kane ; Ryan L. Truby ;
Abstract: Structural electrolytes present advantages over liquid varieties, which are critical to myriad applications. In particular, structural electrolytes based on polymerized ionic liquids or poly(ionic liquids) (pILs) provide wide electrochemical windows, high thermal stability, nonvolatility, and modular chemistry. However, current methods of fabricating structural electrolytes from pILs and their composites present limitations. Recent advances have been made in 3D printing pIL electrolytes, but current printing techniques limit the complexity of forms that can be achieved, as well as the ability to control mechanical properties or conductivity. We introduce a method for fabricating architected pIL composites as structural electrolytes via embedded 3D (EMB3D) printing. We present a modular design for formulating ionic liquid (IL) monomer composite inks that can be printed into sparse, lightweight, free-standing lattices with different functionalities. In addition to characterizing the rheological and mechanical behaviors of IL monomer inks and pIL lattices, we demonstrate the self-sensing capabilities of our printed structural electrolytes during cyclic compression. Finally, we use our inks and printing method to spatially program self-sensing capabilities in pIL lattices through heterogeneous architectures as well as ink compositions that provide mixed ionic-electronic conductivity. Our free-form approach to fabricating structural electrolytes in complex, 3D forms with programmable, anisotropic properties has broad potential use in next-generation sensors, soft robotics, bioelectronics, energy storage devices, and more.
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Keywords: 3D printing ; poly(ionic liquids) ; structural electrolytes ; architected materials ; sensors
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A New Nonaqueous Flow Battery with Extended Cycling
Diqing Yue ; Weilin Zhang ; Ivy Zhao ; Xiaoting Fang ; Xiaoting Fang ; Yuyue Zhao , et al.
Abstract: Nonaqueous flow batteries hold promise given their high cell voltage and energy density, but their performance is often plagued by the crossover of redox compounds. In this study, we used permselective lithium superionic conducting (LiSICON) ceramic membranes to enable reliable long-term use of organic redox molecules in nonaqueous flow cells. With different solvents on each side, enhanced cell voltages were obtained for a flow battery using viologen-based negolyte and TEMPO-based posolyte molecules. The thermoplastic assembly of the LiSICON membrane realized leakless cell sealing, thus overcoming the mechanical brittleness challenge. As a result, stable cycling was achieved in the flow cells, which showed good capacity retention over an extended test time.
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Keywords: nonaqueous flow battery ; organic ; permselectivity ; LiSICON ; stability
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CAS No. : | 90076-65-6 |
Formula : | C2F6LiNO4S2 |
M.W : | 287.09 |
SMILES Code : | O=S([N-]S(=O)(C(F)(F)F)=O)(C(F)(F)F)=O.[Li+] |
MDL No. : | MFCD00210017 |
InChI Key : | QSZMZKBZAYQGRS-UHFFFAOYSA-N |
Pubchem ID : | 3816071 |
GHS Pictogram: |
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Signal Word: | Danger |
Hazard Statements: | H301+H311-H314-H372-H412 |
Precautionary Statements: | P260-P264-P270-P273-P280-P301+P310+P330-P301+P330+P331-P303+P361+P353-P304+P340+P310-P305+P351+P338+P310-P314-P361+P364-P405-P501 |
Class: | 8(6.1) |
UN#: | 2923 |
Packing Group: | Ⅱ |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87.1% | In water; at 60℃; for 2h; | 2. Put 200g lithium bistrifluoromethylsulfonimide, 152g 1-ethyl-3-methylimidazole bromide salt and 400g pure water into the reactor,Warm to 60 , react for 2h,After standing for a while, 283 g of crude 1-ethyl-3-methylimidazole bistrifluoromethylsulfonimide salt was obtained. 3. Wash three times with pure water to obtain 251g of pure 1-ethyl-3-methylimidazole bistrifluoromethylsulfonimide salt.Distill it on a rotary evaporator under reduced pressure for 2h,Keep the temperature at 80 , remove most of the water,Finally, it is dried in a vacuum oven at 110 C for 12h.237 g of 1-ethyl-3-methylimidazole bistrifluoromethylsulfonimide was obtained. The purity of the product detected by liquid chromatography was 99.23%, and the yield was 87.1%;Ion chromatography detection: halogen ion 450ppm;ICP detection: Fe ion <1ppm, Pb ion <1ppm. |
86% | In water; at 20℃; for 2h;Heating / reflux; | 9.40 g of methylimidazole (0.115 mol) in 50 ml of ethyl acetate is introduced into a 500 ml three-necked flask equipped with a condenser. 14.25 g of ethyl bromide (0.126 mol) is added dropwise at ambient temperature. Then, the mixture is left for two hours under reflux before being extracted by three times 25 ml of ethyl acetate. The product is dried under vacuum at 70 C. for thirty minutes; this is ethylmethylimidazolium bromide. NMR 1H: (200 MHz, CD3CN): delta 9.42 (t, 1H, Ha); 7.63 (d, 1H, Hb); 7.55 (d, 1H, Hc); 3.93 (s, 3H, Hd); 4.28 (q, 2H, He); 1.50 (t, 3H, Hf) This product is added dropwise at ambient temperature to a mixture containing 50 ml of water and 31.37 g of lithium bis(trifluorosulphonyl)imide (0.109 mol). Then the mixture is stirred for two hours under reflux. The product is then extracted with three times 20 ml of dichloromethane before being evaporated under vacuum at 70 C. for 30 minutes. The overall yield is 86%. NMR 1H: (200 MHz, CD3CN): delta 8.46 (s, 1H, Ha); 7.42 (s, 1H, Hb); 7.37 (s, 1H, Hc); 3.93 (s, 3H, Hd); 4.28 (q, 2H, He); 1.50 (t, 3H, Hf) |
In water; at 70℃; for 24h;pH 6.0; | General procedure: The respective halide IL was dissolved in deionized water (pH =6) and after an equimolar amount of LiNTf2 in water had been added dropwise, the reaction mixture was stirred for 1 day at 70 C. Then CH2Cl2 was added and the aqueous phase was removed. The organic phase was washed halide-free with deionized water (AgNO3 test). The solution was filtered over a column filled with neutral Al2O3 and activated charcoal. The organic solvent was removed under reduced pressure and the reaction product finally dried under dynamic vacuum for 1-2 days at 80-90 C. |
383.5 g | In water; | Step 1: Take 287.1g of lithium bis (trifluoromethanesulfonyl) imide (LiTFSI) completely dissolved in water to form an aqueous solution with a mass percentage concentration of 50%; Step 2: 191.1 g of 1-ethyl-3-methylimidazolium bromide (EMIBr) was completely dissolved in water to form an aqueous solution having a mass percentage concentration of 50% Step 3: mixing the aqueous solution products obtained in steps 1 and 2 to obtain a crude product; Step 4: The crude product is obtained in step 3, washed with water for 2 times, emulsified by heating and stirring, and heated to 60 DEG C for demulsification, and then high purity product is obtained after liquid separation; Step 5: The high-purity product obtained in Step 4 was vacuum-dried at 100 C for 8 hours to obtain 383.5 g of colorless liquid EMI · TFSI product (melting point: about -15 C), purity: 99.95%, water content: 80 ppm, . |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In water; at 20℃; for 1h; | In 4-necked flask of 300ml, 15.8 g (0.200mol) of pyridine, 26.5 g (0.220mol) of 1-chlorohexane, and 50.0g of toluene were added and stirred for 22 hours under reflux (approximately 106C). After they were reacted in this way, a reaction solution was cooled (air-cooled) to 70C or below. Then, 50.5g of ultra pure water was added therein, the resultant solution was water-cooled to room temperature. After the cooling, an upper layer (toluene layer) of the solution was separated off from the solution by using a separating funnel. To a lower layer (organic layer), 50.0g of toluene was further added. After the resultant solution was stirred for 30 min, an upper layer (toluene layer) was separated off from the solution by using a separating funnel, thereby remaining a water layer in which N-n-hexyl pyridinium chloride (hereinafter, referred to as [HPy]Cl) being a cation portion of an ionic liquid was contained.(Anion-Exchange Reaction) After the separation, 126.8g of the solution containing [HPy]Cl (corresponding to 0.200mol of [HPy]Cl) was transferred to a 300ml egg-plant-shaped flask, and mixed with 63.2g (0.220mol) of lithium bis (trifluoromethanesulfonyl) imide. A resultant mixture was stirred for 1 hour at room temperature in order to carry out an anion-exchange reaction. After the reaction, an upper layer (water layer) was separated out by using a separating funnel. A lower layer was mixed with 50.0g of ultra pure water and stirred for 30min at room temperature. Then, an upper layer (water layer) was separated out by using a separating funnel. A lower layer containing the cation portion of the ionic liquid was transferred to an egg-plant-shaped flask of 200ml and evaporated under reduced pressure at 60C under 20mmHg for 1 hour, so as to distill off a solvent. In this way, a light yellow solution containing N-n-hexyl pyridinium bis (trifluoromethanesulfonyl) imide ([HPy]NTf2) was obtained.(Salt Removal Step) After 50.0g of acetone was added thereto, the light yellow solution thus obtained was cooled to a temperature in a range of approximately 0 to 5C, and then stirred for 30 min, thereby trying to crystallize out lithium chloride (by-product) and unreacted lithium bis (trifluoromethanesulfonyl) imide. Even though the crystallization yielded no crystals, the resultant solution was filtered with a Buchner funnel having an internal diameter of 55mm, and then washed with 20.0g of acetone. A filtrate obtained from the filtration was then transferred to an egg-plant-shaped flask of 200ml and evaporated under reduced pressure at 60C under 20mmHg for 3 hours, and then further evaporated under reduced pressure at 60C under 1mmHg to 2mmHg for 1 hour. In this way, 93.4g of a concentrated solution containing the target [HPy]NTf2 was obtained. The concentrated solution had water content of 0.0069% (69ppm).(Water Removing Step and Purifying Step) Then, 93.4g of the concentrated solution thus obtained was mixed with 0.20g (0.00166mol) of methyl orthoacetate (MOA). A resultant mixture was stirred at 80C for 3 hours so as to react MOA with water not distilled off from an ionic liquid. The reaction caused hydrolysis of MOA with the water thereby giving methanol and methyl acetate. The methanol and methyl acetate thus obtained and unreacted MOA were evaporated off under reduced pressure at 60C under 20mmHg for 1 hour. A concentrated liquid thus obtained was further evaporated under reduced pressure at 60C under 1mmHg to 2mmHg for 2 hours. In this way, a target material, [HPy]NTf2 was obtained as a light yellow liquid.(Water Content Analysis of [HPy]NTf2) Water content of [HPy]NTf2 was measured by the Karl Fishcer test. Water content after the addition of MOA was 0.0000% (0ppm). Water content after methanol, methyl acetate and the unreacted MOA was evaporated off was 0.0000% (0ppm). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | In acetonitrile; at 20℃; for 48h; | The ionic liquid EMI?TFSI- was synthesized by a one step methathesis: 1-ethyl-3-methylimidazoliumchloride EMI?Cl- (1.465 g, 0.01 mol) and lithium bis(trifluoromethanesulfonyl)imide (LiTFSI) (2.871 g, 0.01 mol) were dissolved in acetonitrile intwo separate vials. An anion-exchange reaction occurred after adding slowly (drop bydrop) LiTFSI solution in a 10 mL round-bottom flask containing the EMI?Cl- solution,whereby the mixture was precipitated. Then, the reaction mixture was stirred at 500 rpm atroom temperature for 48 h. After removal of the solvent, the mixture was washedrepeatedly with water until the Cl- could not be detected by addition of AgNO3 solution.The organic phase was collected in a vial and was passed at least twice through Celitesilica column with ethyl acetate to completely remove Cl-. After removal of the solvent,the final product was dried under vacuum to give a yellowish liquid (2.347 g, 62 %). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | In water; for 1.0h; | Weigh 100 g of the intermediate product into 200 mL of water to dissolve.Add 130g of trifluoromethylsulfonimide lithium and stir for 1h.Extracted with 400 mL of organic solvent, and after separation, the organic phase was washed 5 times with water to a halogen-free ion.After washing, the finally obtained organic phase was steamed at 80 C for 6 h.Drying to obtain a product ionic liquid; the organic solvent is dichloromethane;Halogen-free ions were detected using AgNO3/HNO3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | In lithium hydroxide monohydrate; at 50℃; for 1h; | Tri-n-butyl(2-propen-1-yl)phosphonium bromide (5.005 g,15.48 mmol) and lithium bis(trifluoromethanesulfonyl)imide(4.759 g, 16.58 mmol) were combined in a round bottom flaskequipped with a magnetic stir bar and dissolved in 50 mL deionizedwater forming a cloudy solution. The mixture was stirred for1 hr at 50 C and then allowed to cool to room temperature. Themixture was transferred to a separatory funnel, and the productwas extracted twice with 10 mL dichloromethane. The organiclayer was washed twice with 10 mL deionized water. Solventwas removed via rotary evaporation. The resulting solid was driedon a vacuum line and stored in a desiccator. Yield: white solid,7.810 g, 97%. Characterization and spectroscopy agree with literatureprecedent [33]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane; water; at 20.0℃; for 24.0h; | General procedure: A dried 250 ml round bottom flask was prepared, and 50 ml of DCM (dichloromethane) was added to 1-(Trimethylsilyl)methyl-1-methylpyrrolidinium chloride (10 g, 0.05 mol) and stirred at room temperature.Lithium bis(fluorosulfonyl)imide (9.2 g, 0.05 mol) and 50 ml of DIW (distilled water) were dissolved in a dropping funnel and added dropwise over 10 minutes.After completion of dropwise addition, the reaction was stirred at room temperature for 24 hours.After completion of the reaction, the organic layer is separated using a separator funnel,The organic layer was washed with 50 ml of DIW. The organic layer was added with MgSO4 and filtered, The solvent was removed by distillation and distillation under vacuum to obtain the desired product, 1-(Trimethylsilyl)methyl-1-methylpyrrolidinium bis(fluorosulfonyl)imide (15g, yield = 90%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73.5% | In water; at 60 - 80℃; for 2h; | 2. Take 200g lithium bistrifluoromethanesulfonimide,Dissolved in 200g pure water, heated to 60 ,Start dropping 235g of 1-ethyl-3-methylimidazole bicarbonate aqueous solution,At the end of the dropwise addition, the temperature rose to 80 C and the temperature was kept for 2 hours. 3. Lower the reaction solution to room temperature,Filtration to obtain 54g of wet filter residue (lithium carbonate and lithium bicarbonate),The filtrate is allowed to stand for separation,286 g of crude 1-ethyl-3-methylimidazole bistrifluoromethylsulfonimide salt was obtained. 4. Wash three times with pure water to obtain 243g of 1-ethyl-3-methylimidazole bistrifluoromethylsulfonimide salt.Distill it on a rotary evaporator under reduced pressure for 2h,Maintain the temperature at 80 , remove most of the water, cool and filter to get 6g of wet filter residue,Finally, it is dried in a vacuum drying oven at 110 for 12 hours, and the moisture content is less than 500ppm.The temperature was lowered and filtered to obtain 203g of 1-ethyl-3-methylimidazole bistrifluoromethylsulfonimide salt. Liquid chromatography detection product purity was 97.62%, yield was 73.5%;Ion chromatography detection: halogen ion <1ppm;ICP detection: Fe ion <1ppm, Pb ion <1ppm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90.6% | In water; at 60℃; for 2h; | 3. Combine 200g of 1-ethyl-3-methylimidazole ethyl sulfate,243g of lithium bistrifluoromethanesulfonimide,500g pure water was put into the reaction kettle,Raise the temperature to 60 , stir the reaction for 2h, let it stand for phase separation,335 g of crude 1-ethyl-3-methylimidazole bistrifluoromethylsulfonimide was obtained. 4. The crude 1-ethyl-3-methylimidazole bistrifluoromethylsulfonimide was washed three times with pure water to obtain 312g of relatively pure 1-ethyl-3-methylimidazole bistrifluoromethylsulfonimide amine,Distill it on a rotary evaporator under reduced pressure for 2h,Keep the temperature at 80 , remove most of the water, and finally dry in a vacuum drying cabinet at 110 for 12h.301 g of the target product 1-ethyl-3-methylimidazole bistrifluoromethylsulfonimide was obtained. The purity of the product detected by liquid chromatography was 99.6%, and the yield reached 90.6%;Ion chromatography detection: halogen ion content <1ppm;ICP detection: Fe ion <1ppm, Pb ion <1ppm. |