Chloroform d

Manufactured by Thermo Fisher Scientific

Sourced in Sweden, Belgium, United Kingdom, United States

Chloroform-d is a deuterated chloroform compound commonly used as a nuclear magnetic resonance (NMR) solvent. It is a clear, colorless liquid with a characteristic odor. Chloroform-d is often employed in analytical chemistry and spectroscopic techniques to dissolve and analyze organic compounds.

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10 protocols using chloroform d

Thermoplastic Carrier Synthesis and Characterization

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The diglycidyl ether of bisphenol A (DGEBA, epoxide equivalent weight 172–176), polyvinyl alcohol (PVA-13k, average M_w 13,000–23,000, 87–89% hydrolyzed), polyvinyl alcohol (PVA-146k, average Mw 146,000–186,000, 87–89% hydrolyzed), and aluminum oxide (activated, basic, Brockmann I) were purchased from Sigma-Aldrich (St. Louis, MO). Methyl methacrylate (MMA, ≥98 %, Stabilized/Certified ACS) which was used as the monomer for producing the thermoplastic carrier was obtained from Fisher Chemical (Fair Lawn, NJ). The initiator, benzoyl peroxide (BPO, 75% remainder water), and chloroform-d (99.8% atom D) was purchased from ACROS Organics (Morris Plains, NJ).

Yang G., Xie W., Huang M., Champagne V.K., Lee J.H., Klier J, & Schiffman J.D. (2018). Polymer Particles with a Low Glass Transition Temperature Containing Thermoset Resin Enable Powder Coatings at Room Temperature. Industrial & engineering chemistry research, 58(2), 908-916.

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Synthesis of Xanthate-Functional Polymers

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N-Vinylpyrrolidone (≥97% FLUCA, Bucharest, Romania) containing sodium hydroxide as inhibitor was dried overnight over calcium hydride and was distilled prior to use. Isobornyl methacrylate (TCI Chemicals, Tokyo, Japan) stabilized with methyl hydroquinone, was dried as well over calcium hydride overnight and then passed through a MEHQ inhibitor remover column. Azobisisobutyronitrile AIBN (98% ACROS Chemicals, Gotëborg, Sweden) was purified by recrystallization twice from methanol and was then dried under vacuum. The chain transfer agent [(O-ethylxanthyl)methyl]benzene was synthesized according to the literature [40 (link)]. Chloroform-d (Acros Organics, Gotëborg, Sweden) was used as purchased. 1,4-dioxane (Fisher Chemicals, Loughborough, UK) was passed through a basic alumina (Al₂CO₃) column.

Kokkorogianni O., Kontoes-Georgoudakis P., Athanasopoulou M., Polizos N, & Pitsikalis M. (2021). Statistical Copolymers of N-Vinylpyrrolidone and Isobornyl Methacrylate via Free Radical and RAFT Polymerization: Monomer Reactivity Ratios, Thermal Properties, and Kinetics of Thermal Decomposition. Polymers, 13(5), 778.

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Functionalized POEGMA Polymer Synthesis

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Ethyl alcohol, dimethylformamide (DMF), copper chloride, tetrahydrofuran (THF), 4,4′-dinonyl-2,2′-dipyridyl, oligomers of poly(ethylene glycol) methyl ether methacrylate (POEGMA) with molecular weight: 144, 188 and 300, 11-mercapto-1-undecanol, pyridine, α-bromoisobutyryl bromide, sodium sulphate, potassium chloride were purchased from Sigma Aldrich. Dichloromethane (DCM) was purchased from Alfa Aesar. Triethyoxysilane, Alumina and chloroform-D were purchased from ACROS organics. All chemicals were used with no further purification, with the exception of POEGMA oligomers that were purified through an inhibitor removal column (Sigma Aldrich, cat no. 306312) to increase the reactivity of the chemical. Millipore water from Thermo scientific barnstead SMART2PURE UV/UF water filter was used for experiments. Gold plated QCM-D crystals were purchased from Nanoscience Instruments (QSM 301).

Guntnur R.T., Muzzio N., Morales M, & Romero G. (2021). Phase Transition Characterization of Poly (oligo (ethylene glycol) methyl ether methacrylate) Brushes using the Quartz Crystal Microbalance with Dissipation. Soft matter, 17(9), 2530-2538.

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Synthesis and Purification of AGC12 Monomer

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The amphiphilic monomer AGC₁₂ was prepared and purified according to our previous work, and their synthetic routes are shown in Scheme 2 [25 (link)]. The detailed synthetic procedure of AGC₁₂ was given in Supplementary Materials. Deuterium oxide (99.9%) and chloroform-d (99.9%) were purchased from Acros (Geel, Belgium. Acryloyl chloride, 1-bromine octane and solvents were purchased from Beijing Chemical Co. (analytical reagent (AR) grade, Beijing, China). The used halloysite clay nanotubes (HNTs) were obtained from Nanyang Hongfa Bentonite Company in Nanyang, China. Acrylamide (AM) was obtained from Acros and purified via recrystallization before use. 3-aminopropyltriethoxysilane (APTES, 98%), serving as a silica source was supplied by Sigma-Aldrich (St Louis, MI, USA). and used as received. Methenamine, used for guest loading, was purchased from Alfa Aesar (Ward Hill, MA, USA).

Zhang M., Wang J., Zhang P, & Yan H. (2018). Surface-Engineered Nanocontainers Based on Molecular Self-Assembly and Their Release of Methenamine. Polymers, 10(2), 163.

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NMR Characterization of SSXL Synthesis

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The composition of raw materials, purification fractions, and final product of the SSXL synthesis were confirmed using a Varian (Palo Alto, CA) DirectDrive 400 MHz nuclear magnetic resonance spectrometer equipped with an automatic sampler. Chloroform-d (CDCl₃, 99.8%) was obtained from Acros Organics (Fairlawn, NJ). SSXL was dissolved at 1% (vol/vol) in CDC₁₃ for 1H-NMR analysis. All NMR spectra were analyzed using SpinWorks 3™ software.

Liechty W.B., Scheuerle R.L., Vela Ramirez J.E, & Peppas N.A. (2019). Cytoplasmic Delivery of Functional siRNA Using pH-Responsive Nanoscale Hydrogels. International journal of pharmaceutics, 562, 249-257.

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Synthesis and Characterization of BHED Derivatives

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Bis(2-hydroxyethyl)disulfide (BHED), 1,1’-carbonyldiimidazole (CDI), tris(2-aminoethyl) amine, heptafluorobutyric anhydride (HFBA), Amberlite IR120 Na⁺ form, and glutathione (GSH) were purchased from Sigma-Aldrich (St. Louis, MO). Dichloromethane (DCM), methanol, and acetonitrile were purchased from Fisher Scientific (Waltham, MA). Dimethyl sulfoxide-d6 (DMSO-d6), deuterium oxide, and chloroform-d were purchased from Acros Organics (Fair Lawn, NJ). BENSpm was synthesized as previously described.^{70 (link)} McCoy’s 5A medium; RPMI1640 medium; DMEM high glucose medium, Dulbecco’s phosphate buffered saline (PBS), fetal bovine serum (FBS), penicillin/streptomycin (Pen-Strep) and trypLE express reagent were purchased from Thermo Fisher Scientific (Waltham, MA).

Yu A., Tang S., Ding L., Foley J., Tang W., Jia H., Panja S., Holbert C.E., Hang Y., Stewart T.M., Smith L.M., Sil D., Casero RA J.r, & Oupický D. (2022). Hyaluronate-coated perfluoroalkyl polyamine prodrugs as bioactive siRNA delivery systems for the treatment of peritoneal cancers. Biomaterials advances, 136, 212755.

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Synthesis of Acrylic Polymer Precursors

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Methyl methacrylate (MMA), n-butyl acrylate (nBA), chloroform, methyl ethyl ketone (MEK), and initiator azobisisobutyronitrile (AIBN) were purchased from Sigma-Aldrich and used as received. Hexane and tetrahydrofuran (THF) were purchased from Thermo Fisher-Scientific and used as received. chloroform-D was purchased from ACROS Organics.

Davydovich D, & Urban M.W. (2020). Water accelerated self-healing of hydrophobic copolymers. Nature Communications, 11, 5743.

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Synthesis and Characterization Protocol

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Syntheses were carried out under a nitrogen atmosphere, unless stated otherwise. Glassware was dried before use. Solvents were dried over 4 Å molecular sieves for at least 24 h before use.
n-Butyllithium (n-BuLi, 2.5 M, in hexanes), chloroform-d (99.8 atom% D) and n-octane ($97%) were obtained from Acros, bromine (Br 2 , $99.99% trace metals basis), 9,10-diphenylanthracene, hydrochloric acid (HCl, 37%), magnesium silicide (Mg 2 Si, $99% trace metals basis, À20 mesh), molecular sieves (0.3 nm, rods), sodium sulfate (Na 2 SO 4 , anhydrous), and sodium thiosulfate (Na 2 S 2 O 3 , $98%, anhydrous) were obtained from Sigma Aldrich, chloroform, ethanol, ethyl acetate and methanol were obtained from VWR, TEM grids were obtained from EM Resolutions (Sheffield, United Kingdom), and XPS substrates from SSENS (Hengelo, The Netherlands).

Wilbrink JL ., Huang CC ., Dohnalova K , & Paulusse JMJ . (2020). Critical assessment of wet-chemical oxidation synthesis of silicon quantum dots. Faraday discussions, 222(0).

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NMR Spectroscopy of 15 mg Sample

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Nuclear Magnetic Resonance ¹H and 13 C spectra were obtained on a 300 MHz equipment (Fourier 300 model, Bruker, Massachusetts, USA), using 550 μL of chloroform-d (Acros Organics, Massachusetts, USA) in a tube of 5 mm to solubilize 15 mg of sample.

Ferreira R.G.d.S., Guilhon‐Simplicio F., Yamaguchi K.K.d.L., Lira P.D.d., Machado T.M., Ferreira M.A.C., Veiga V.F.d., & Lima É.S. (2020). The selective obtaining of amyrins from Amazonian Protium oleoresins. Revista Colombiana de Ciencias Químico Farmacéuticas, 49(2).

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Synthesis of Functional Latex Polymers

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Diethyl methylene malonate (Chemi-lian M1000, DEMM) and Forza B3100 (DEMM)₆ were provided by Sirrus Inc. (Loveland, OH). Methyl methacrylate (MMA, Fisher), butyl acrylate (BA, Acros Organics), and methacrylate acid (MAA, Sigma-Aldrich) were used as monomers for latex synthesis. 2,2′-Azobis[2-(2-imidazolin-2-yl) propane] dihydrochloride (AIBI, TCI) was used as an initiator, and Triton X-405 (Sigma-Aldrich) was used as a surfactant. Acrylic acid (AA, Sigma-Aldrich), catechol (Acros Organics), 2-vinylbenzoic acid (VBA, Fisher), and benzeneboronic acid (BBA, Alfa Aesar) were used to prepare initiators for DEMM polymerization. Aluminum oxide (Sigma-Aldrich) was used to remove the inhibitor from monomers. N,N-Dimethylformamide (DMF, Fisher) was used as an extractor. Deuterium oxide (D₂O, 99.8% atom D), chloroform-d (CDCl3, 99.8% atom D), and methyl sulfoxide-d₆ (DMSO-d₆, 99.5+% atom D) were obtained from Acros Organics. Doubly deionized (DDI) water was used throughout the work.

Huang M., Liu Y., Yang G., Klier J, & Schiffman J.D. (2019). Anionic Polymerization of Methylene Malonate for High-Performance Coatings. ACS applied polymer materials, 1(4), 657-663.

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