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Deuterated chloroform

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Deuterated chloroform is a stable isotope of chloroform where the hydrogen atoms have been replaced with deuterium. It is commonly used as a solvent in nuclear magnetic resonance (NMR) spectroscopy and other analytical techniques.

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30 protocols using deuterated chloroform

1

Oxidation of alcohols with PS-TEMPO

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Deuterated chloroform was obtained from Cambridge Isotope Laboratories Inc. (Andover, MA. USA), and used without further purification. TEMPO functionalized polystyrene, 2% cross-linked with divinylbenzene, (PS-TEMPO) was obtained from Biotage® (Uppsala, Sweden) and used without further purification. 1-Dodecanol was obtained from Aldrich (St. Louis, Missouri, MO, USA) and used without further purification. Phenethyl alcohol was obtained from Matheson Coleman & Bell (MCB) (Washington, DC, USA) and used without further purification. Other alcohols and oxidants were obtained from Fisher Scientific (Hampton, New Hampshire, NH, USA) and used without further purification. 1H NMR spectroscopy was performed using a Bruker Avance 400 spectrometer (Billerica, Massachusetts, MA, USA). The temperature of the vial was determined by use of a temperature logging “iButton” (DS1922E-F5#, Maxim Integrated Circuits, San Jose, California, CA, USA http://www.ibutton.com) clamped against the vial. This temperature rises for approximately the first hour and then maintains for the remainder of the experiment.
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2

NMR and GPC-MALS Polymer Characterization

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Nuclear magnetic resonance (NMR) spectra were recorded on a Bruker Avance-III 300 MHz spectrometer or a Varian Inova 400 MHz spectrometer. Chemical shifts were referenced using internal solvent resonance, 7.26 ppm for CDCl3 and 7.16 ppm for C6D6. Deuterated chloroform was purchased from Cambridge Isotope Laboratories.
Analysis of polymer molecular weight and dispersity was performed using gel permeation chromatography (GPC) coupled with multi-angle light scattering (MALS), using an Agilent HPLC fitted with one guard column and three PLgel 5 μm MIXED-C gel permeation columns in series. The detectors used were a Wyatt Technology TrEX differential refractometer and a Wyatt Technology miniDAWN TREOS light scattering detector, which allows the direct measurement of absolute Mw and does not require any correction factor for accurate MW measurement. The solvent used was THF with a flow rate of 1.0 mL/minute.
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3

Synthesis of Electrolyte Components

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Potassium hydroxide (≥85%), sodium
sulfate (anhydrous), sodium hydride (60%, in mineral oil), 2,2,3,3,3-pentafluoro-1-propanol
(97%), 2,2,2-trifluoroethanol (99%), 1 M LiPF6 in EC/DMC
(50:50 v/v, battery grade), diethylene glycol (99%), triethylene glycol
(99%), tetraethylene glycol (99%), diglyme (anhydrous), α,α,α-trifluorotoluene
(99%), tetraglyme (anhydrous), and 4 Å molecular sieves were
purchased from Sigma-Aldrich. Acetone (99.5%), tetrahydrofuran (certified
grade, with 0.025% butylated hydroxytoluene as a preservative), dichloromethane
(99.5%), hexanes (98.5%), ethyl acetate (99.5%), and methanol (99.8%)
were purchased from Fisher. Lithium foil (750 μm thick), p-toluenesulfonyl chloride (98%), and triglyme (99%) were
purchased from Alfa Aesar. Lithium perchlorate (99%), lithum bis(fluorosulfonyl)
amide (99%), and pentaethylene glycol (95%) were purchased from Oakwood
Chemical. Deuterated acetonitrile (≥99.8 atom % D) and deuterated
chloroform (≥99.8 atom % D) were purchased from Cambridge Isotope
Laboratories. All solvents used for preparing electrolytes were dried
by 4 Å molecular sieves overnight inside an argon-filled glovebox
(VigorTech, O2 and H2O < 1 ppm). LiFSA salt
was vacuum-dried at 120 °C overnight in a heated glovebox antechamber
before use and was not exposed to air at any time. Other chemicals
were used as received.
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4

Synthesis and Characterization of Organic Compounds

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Commercially
available compounds
were purchased from Alfa Aesar, ACROS, or Sigma–Aldrich and
used as received. The solvents were purchased from Fisher Scientific
and dried via a Glass Contour solvent purification system. For reactions
requiring elevated temperatures, reaction mixtures were heated using
heat blocks contoured to the size and shape of the flask. Column chromatography
was performed on either a Biotage instrument or on hand-packed silica
gel flash columns. Air and moisture-sensitive compounds were manipulated
under nitrogen using a Schlenk technique or in a nitrogen-filled glovebox. 1H and 13C NMR spectra were recorded on JEOL and
Agilent 400 MHz NMR spectrometers. Deuterated chloroform was purchased
from Cambridge Isotope Laboratories. Chemical shifts (δ) are
reported in parts per million and referenced to the internal standard,
tetramethylsilane (TMS), and/or the residual solvent peaks (e.g.,
CHCl3). High-resolution mass spectrometry (HRMS) data were
obtained on a Hybrid Quadrupole-Orbitrap Mass Spectrometer or APCI-Q-TOF.
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5

Comprehensive Organic Chemical Acquisition

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Carbon tetrachloride, cyclohexane, benzene, toluene, o-xylene, m-xylene and p-xylene, mesitylene, and phenol were purchased from Beijing Chemical Reagent Factory. Ethylbenzene, benzyl alcohol and benzaldehyde were purchased from Tianjin Chemical Reagent Factory. Deuterated chloroform was purchased from Cambridge Isotope Laboratories, Inc. (Massachusetts, USA). All reference standards were supplied by the Chinese Food and Drug Inspection Institute (Beijing, China).
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6

Analytical Characterization of CBD Oil

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As a representative of a widely marketed product, a “highly concentrated CBD oil containing 1,500+ mg cannabinoids per fluid ounce” was obtained from Bluebird Botanicals (Louisville, CO, USA). Samples were stored at −20 °C until analyzed. Deuterated chloroform was obtained from Cambridge Isotope Laboratories, Inc. (Andover, MA, USA). HPLC grade solvents and other chemicals were reagent grade from Sigma-Aldrich Inc. (St. Louis, MO, USA). All organic solvents were analytical grade, purchased from Pharmco-AAPER (Crookfield, CT, USA), and distilled before use. The external calibrant, dimethyl sulfone (Code N. 048–33,271; 99.9 % purity), was from Wako Pure Chemical Ind., Ltd. (Osaka, Japan).
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7

Synthesis and Characterization of Copolymers

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Chemicals used for monomer and polymer synthesis included sodium hydroxide, hydrobenzoic acid, dibromohexane, 1-methyl-2-pyrrolidinone, SA monomer, and triethylene glycol purchased from Sigma Aldrich (St. Louis, MO, USA). Acetic anhydride, ethyl ether, petroleum ether, chloroform, methylene chloride, hexane, acetone, sulfuric acid, potassium carbonate, dimethyl formamide, toluene, acetonitrile, N,N-dimethylacetamide, and acetic acid were purchased from Fisher Scientific (Fairlawn, NJ, USA); 4-p-fluorobenzonitrile was purchased from Apollo Scientific (Cheshire, UK). For 1H NMR analysis of the copolymers, deuterated chloroform and dimethyl sulfoxide were purchased from Cambridge Isotope Laboratories (Andover, MA, USA). The N-terminal region of a recombinant PspA (UAB055, PspA/Rx1 AA1 to 303, clade 2 PspA of the PspA family 1) was produced by Dr. David McPherson (University of Alabama at Birmingham) as described previously (55 (link)). Prior to immunization, endotoxin was removed from the protein using endotoxin removal beads (Miltenyi Biotec, Bergisch Gladbach, Germany) according to the manufacturer’s instructions followed by dialysis and lyophilization. The final endotoxin content of the protein was determined to be less than 1.9 EU/mg as determined by a limulus amebocyte lysate chromogenic endotoxin quantification kit (Thermo Fisher Scientific).
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8

Synthesis and Characterization of Compounds 1-17

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Unless specifically noted otherwise, synthetic reactions were carried out in flame or oven-dried glassware under Argon, with the exception of reactions run in water as co-solvent. All reactions were stirred using a magnetic stir bar. Deuterated chloroform for NMR, with 0.03% TMS as reference, was purchased from Cambridge Isotope Laboratories. NMR spectra were collected on a Varian 500 MHz spectrometer or a Varian 500 MHz spectrometer equipped with an inverse cryo-probe. HR-ESI-TOF-MS data were collected by the Molecular Mass Spectrometry Facility at UCSD. Purity of the final products 1-17 was assessed as being above ≥95% by evaluation of their 1H NMR and 13C NMR spectra.
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9

Purification and Characterization of SWCNTs

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Unless otherwise noted, compounds and solvents
were purchased from commercial suppliers and used without further
purification. Synthesized compounds were purified using flash column
chromatography [CombiFlash Companion, Teledyne ISCO, Lincoln, NE,
USA; column: Kanto Silica Gel 60 (spherical: 63–210 μm),
Kanto Chemical Co., Inc., Tokyo, Japan]. Deuterated chloroform was
purchased from Cambridge Isotope Laboratories Inc. (Tewksbury, MA,
USA). The high-pressure catalytic CO (HiPCO) SWCNTs were purchased
from Nano-C Inc. (Westwood, MA, USA; 70 wt % carbon with >85% SWCNTs,
1.0–1.1 μm length, 0.9–1.3 nm diameter) and were
used as received. The metallic residue in the raw SWCNTs was estimated
to be 18% using inductively coupled plasma (ICP) emission spectrometry.
PC61BM was purchased from Tokyo Chemical Industry Co.,
Ltd. (Tokyo, Japan).
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10

Myrcene Cycloaddition Reactions and Analyses

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The reactants myrcene (1, 90% purity), maleic anhydride (2a), acrylic acid (2b), itaconic acid (2c), dimethyl maleate (2d), ethyl acrylate (2f) and poly(ethylene glycol) methyl ether acrylate (PEGA, 2g) were obtained from Sigma-Aldrich; bis(2-ethylhexyl) maleate was provided by TriTech Lubricants. The solvents tetrahydrofuran (THF), ethyl acetate (EtOAc), toluene, dichloromethane (DCM) and isopropanol (iPrOH) were obtained from Merck KGaA. All reagents and solvents were used without further purification.
Reaction conversions were calculated from 1H NMR spectra, which were recorded on a Bruker AC-400 spectrometer in deuterated chloroform (from Cambridge Isotope Laboratories Inc.). Conversion calculations were based on clearly identifiable and non-convoluted peaks of remaining starting material and generated product. The residual solvent peak at δ = 7.26 ppm was used as an internal reference. Product compositions were analyzed by GC–FID and GC–MS; details for both can be found in Supporting Information File 1. The GC–FID results were also used to confirm NMR conversions and to calculate GC-based yields.
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