By using J. Young valve NMR tubes, the samples of rare earth metal catalysts were prepared for NMR spectroscopic measurements in the glove box. 1H, 13C NMR spectra of ligand and catalysts were tested on a Bruker AVANCE 400 spectrometer in C6D6 or C7D8 at room temperature. 1H, 13C NMR spectra of polyisoprene (PIP), polymyrcene (PMY) and polystyrene (PST) samples were recorded on a Bruker AVANCE 400 spectrometer in CDCl3 at room temperature or at 60 °C. The molecular weights and the molecular weight distributions (PDI) of the poly(conjugated dienes)s were performed at 25 °C by gel permeation chromatography (GPC) on a WATERS 1515 apparatus. THF was selected as the eluent at a flow rate of 1 mL/min. For SPSTs, GPC data were performed in 1,2,4-trichlorobenzene at 150 °C using IR detection and calibration against polystyrene. Differential scanning calorimetry (DSC) measurements were carried out on a TA 60 (TA Co.) at a rate of 10 °C/min. Any thermal history difference in the poly(conjugated diene)s was eliminated by first heating the specimen to 100 °C, cooling at 10 °C/min to –100 °C, and then recording the second DSC scan. For SPSTs, DSC parameter was set to 10 °C/min to speed up to 300 °C, then cooled at 10 °C/min to room temperature, before recording the second DSC scan. Elemental analyses were performed on an Elementary Vario MICRO CUBE (Germany).
Avance 400 spectrometer
Manufactured by Bruker
Sourced in Germany, United States, Switzerland, Italy, United Kingdom, Spain
The Avance 400 spectrometer is a nuclear magnetic resonance (NMR) instrument manufactured by Bruker. It is designed to analyze the chemical structure and composition of samples using the principles of NMR spectroscopy. The Avance 400 spectrometer operates at a frequency of 400 MHz and is capable of performing a wide range of NMR experiments to study a variety of sample types.
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Hp1100, by Agilent Technologies (6 mentions)
Esquire 3000 plus, by Bruker (5 mentions)
Topspin 3, by Bruker (5 mentions)
Nicolet 6700 ft ir spectrometer, by Thermo Fisher Scientific (4 mentions)
Spectrum 400, by PerkinElmer (4 mentions)
Spectrum rx 1 spectrometer, by PerkinElmer (4 mentions)
Spectrum 100 ft ir, by PerkinElmer (4 mentions)
Cdcl3, by Cambridge Isotopes (3 mentions)
Ascend 500 spectrometer, by Bruker (3 mentions)
Vertex 70v, by Bruker (3 mentions)
Silica gel 60 f254, by Merck Group (3 mentions)
Nicolet is50, by Thermo Fisher Scientific (3 mentions)
Avance 2 300, by Bruker (2 mentions)
Avatar 380 ftir spectrometer, by Thermo Fisher Scientific (2 mentions)
Agilent 1290 infinity 2 lc, by Agilent Technologies (2 mentions)
Agilent 6550 ifunnel q tof lc ms, by Agilent Technologies (2 mentions)
Mmao 12, by Merck Group (2 mentions)
Avance 600 spectrometer, by Bruker (2 mentions)
308 protocols using avance 400 spectrometer
1
Characterization of Rare Earth Metal Catalysts
2
Characterization of Material Properties
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All nuclear magnetic
resonance (NMR) measurements were obtained on AVANCE 400 Bruker spectrometer
(DMSO-d6 as solvent). Fourier transforms
infrared (FTIR) spectra were performed by VERTEX 70, Bruker (Germany).
The mass spectra (MS) was conducted by impact (Germany). The limiting
oxygen index (LOI) values used a JF-3 oxygen index meter (China).
The UL-94 vertical burning test used the CZF-5CD 50W vertical burning
instrument (China). The thermogravimetric analysis (TGA) of samples
was performed on a NETZSCH STA449F3 thermal analyzer from 30 to 700
°C under a nitrogen atmosphere with a heating rate of 20 K/min.
Microscale combustion calorimeter (MCC) test was conducted by using
FAA Micro Calorimeter. The Zeiss Sigma 300 SEM was used to observe
scanning electron microscope (SEM) images. The scalable 250xi Thermo
Fisher Scientific was used to record the X-ray photoelectron spectroscopy
(XPS) of char residue. All physical property measurements were measured
on AG-X plus 100KN (SHIMADZU) Universal Material Testing Machine.
The size of stretching properties of specimens was 4 × 10 ×
40 mm. The size of compressive properties of specimens was 10 ×
10 × 10 mm.
resonance (NMR) measurements were obtained on AVANCE 400 Bruker spectrometer
(DMSO-d6 as solvent). Fourier transforms
infrared (FTIR) spectra were performed by VERTEX 70, Bruker (Germany).
The mass spectra (MS) was conducted by impact (Germany). The limiting
oxygen index (LOI) values used a JF-3 oxygen index meter (China).
The UL-94 vertical burning test used the CZF-5CD 50W vertical burning
instrument (China). The thermogravimetric analysis (TGA) of samples
was performed on a NETZSCH STA449F3 thermal analyzer from 30 to 700
°C under a nitrogen atmosphere with a heating rate of 20 K/min.
Microscale combustion calorimeter (MCC) test was conducted by using
FAA Micro Calorimeter. The Zeiss Sigma 300 SEM was used to observe
scanning electron microscope (SEM) images. The scalable 250xi Thermo
Fisher Scientific was used to record the X-ray photoelectron spectroscopy
(XPS) of char residue. All physical property measurements were measured
on AG-X plus 100KN (SHIMADZU) Universal Material Testing Machine.
The size of stretching properties of specimens was 4 × 10 ×
40 mm. The size of compressive properties of specimens was 10 ×
10 × 10 mm.
3
Characterization of Polymer-Drug Conjugates
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1H NMR spectra of TK-C.L. and mPEG-TK-COOH polymer were acquired on Bruker Avance400 NMR (Bruker Biospin, Rheinstetten, Germany) in CDCl3. In the case of mPEG-TK-MPH and mPEG-MPH prodrugs, the 1H NMR spectra were also acquired on Avance400-Bruker spectrometer in CD3OD. For all 1H NMR spectra, tetramethylsilane (TMS) was used as an internal standard. The identification of all proton signals in mPEG-TK-MPH and mPEG-MPH was completed after 1D and 2D (COSY) 1H NMR analyses.
TK-C.L. mass spectra were acquired with Q-TOF Accurate-Mass G6520A—Agilent Technologies, from which an ESI-MS spectrum in negative mode was obtained. Mass spectra of mPEG-TK-COOH, mPEG-TK-MPH, and mPEG-MPH were acquired with a Bruker Ultraflex TOF/TOF, MALDI-TOF/TOF mass spectrometer.
TK-C.L. mass spectra were acquired with Q-TOF Accurate-Mass G6520A—Agilent Technologies, from which an ESI-MS spectrum in negative mode was obtained. Mass spectra of mPEG-TK-COOH, mPEG-TK-MPH, and mPEG-MPH were acquired with a Bruker Ultraflex TOF/TOF, MALDI-TOF/TOF mass spectrometer.
4
NMR Characterization of C1-C4 Polymers
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Chemical structures of C1–C4 polymers were confirmed using 1H NMR, 13C NMR and 19F NMR spectra. Spectra for C1 and C3 were previously reported in [61 (link)], spectra for C4 were previously reported in [62 (link)].
The 1H and 13C NMR spectra of C1–C3 samples were measured on an Avance 400 Bruker spectrometer (400.13 and 100.61 MHz, respectively) using CDCl3 solutions; Me4Si was used as an internal standard. Signals in the 1H and 13C NMR spectra were assigned according to the data calculated using program ACDLabs. 19F NMR for C2 sample was recorded on an Avance 300 Bruker spectrometer (282.40 MHz) (Billerica, MA, USA) for solution in CDCl3 using CF3COOH as the external standard.
Results of 1H NMR and 13C NMR analyses are provided inTables S1 and S2 (Supplementary Materials) , respectively.
The 19F NMR spectrum of sample C2 contains a singlet in the region of minus 63.90 ppm, which is characteristic of the chemical shift of the CF3 group.
The 1H and 13C NMR spectra of C1–C3 samples were measured on an Avance 400 Bruker spectrometer (400.13 and 100.61 MHz, respectively) using CDCl3 solutions; Me4Si was used as an internal standard. Signals in the 1H and 13C NMR spectra were assigned according to the data calculated using program ACDLabs. 19F NMR for C2 sample was recorded on an Avance 300 Bruker spectrometer (282.40 MHz) (Billerica, MA, USA) for solution in CDCl3 using CF3COOH as the external standard.
Results of 1H NMR and 13C NMR analyses are provided in
The 19F NMR spectrum of sample C2 contains a singlet in the region of minus 63.90 ppm, which is characteristic of the chemical shift of the CF3 group.
5
Characterization of Organic Compounds
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Reagents and solvents were used as received from commercial suppliers. 1H NMR spectra were obtained on a Bruker AVANCE 400 spectrometer at 400 MHz with tetramethylsilane was used as an internal standard for proton spectra. Thin-layer chromatography was performed using Merck TLC silica gel 60 F254 plates. Visualization of TLC plates was performed using UV light (220, 230 nm). The mass spectra were obtained on a Waters Acquity LC-MS spectrometer using Electrospray Ionization. HPLC analysis were performed with using the method shown below and gradient found in Supplementary Table 3 .
6
Characterization of Boron Compounds
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NMR spectra were measured on a Bruker Avance-400 spectrometer and chemical shifts (δ) are reported in parts per million (ppm). 1H NMR and 11B NMR spectra were recorded at 400 MHz in NMR solvents and referenced internally to corresponding solvent resonance. Infrared spectra were collected on a Thermo Fisher Nicolet 6700 FT-IR spectrometer using ATR (Attenuated Total Reflectance) method. Absorption maxima (ν max) are reported in wavenumbers (cm–1). Dilution ratios were determined with inductively coupled plasma mass spectrometry (ICP-MS; NexION350D).
7
Synthesis and Characterization of DOPAL
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DOPAL was synthesized by rearrangement of epinephrine, following the method by Robbins49 (link). The product was characterized by means of NMR spectroscopy using a Bruker AVANCE 400 spectrometer. The purity of obtained DOPAL was confirmed through HPLC by using a Jasco MD-1510 instrument with spectrophotometric diode array detection equipped with a Waters Symmetry C18 reverse-phase column (250 × 4.6 mm). Elution was carried out starting with 0.1% trifluoroacetic acid in water for 5 min, followed by a linear gradient, in 40 min, to 100% acetonitrile with 0.1% trifluoroacetic acid. The flow rate was 0.8 mL/min.
8
Silica Gel Chromatography and NMR Characterization
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All reactions were monitored by TLC on aluminum sheets coated with silica gel 60F254 (0.2-mm thickness, Merck) and the components present were detected by charring with 10% H2SO4 in MeOH. Column chromatography was carried out using silica gel 60 (particle size 0.040–0.063 mm, 230–400 mesh ASTM, Merck). Solvent extracts were dried with anhydrous MgSO4 unless otherwise specified. The 1H and 13C NMR spectra were recorded on a Bruker Avance 400 spectrometer at 400 and 101 MHz, respectively. CDCl3 was used as solvent (unless otherwise indicated), δH values are relative to internal TMS and δC values are referenced to the solvent [δC (CDCl3) = 77.0].
9
Spectroscopic Characterization of Compounds
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Mass spectra were recorded on a Bruker Esquire 3000 Plus, with the electrospray (ESI) technique. UV−Vis spectra were recorded with 1 cm quartz cells on an Evolution 600 spectrophotometer (Thermo Electron Scientific Instrument LCC, Madison, WI, USA). 1H, 13C{1H} and 19F NMR (CFCl3 used as standard), including 2D experiments, were recorded at room temperature on a Bruker Avance 400 spectrometer (Bruker, Billerica, MA, USA) (1H, 400 MHz, 13C, 100.6 MHz, 19F, 376.5 MHz) or on a Bruker Avance II 300 ((Bruker, Billerica, MA, USA) (1H, 300 MHz; 13C, 75.5 MHz; 19F, 282.3 MHz) with chemical shifts (δ, ppm) reported relative to the solvent peaks of the deuterated solvent [50 (link)].
10
NMR Spectroscopy and Chromatography Techniques
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NMR spectra were recorded in CDCl3 on a Bruker Avance 400 spectrometer (Billerica, MA, USA). The chemical shifts are given in δ (ppm) with residual deuterated solvent as an internal reference and coupling constants in Hz.
Precoated TLC silica gel 60 F254 aluminum sheets from Sigma-Aldrich were used for thin-layer chromatography (0.25 and 0.5 mm layer thickness for analytical and preparative TLC, respectively) and visualized under short (254 nm) and long (366 nm) wavelength UV light or a spray reagent (H2SO4− AcOH−H2O, 1:20:4). Column chromatography (CC) was conducted using silica gel 60 (63–200, 40–63, or 2–25 μm particle size) or Sephadex LH-20 from Sigma-Aldrich (Saint Louis, MO, USA).
The bioassays were performed inside a laminar flow hood, brand NuAire (Playmouth, MN, USA), class II, type A2. The cells were kept inside a CO2 incubator with a water jacket and HEPA filter, brand NuAire.
Precoated TLC silica gel 60 F254 aluminum sheets from Sigma-Aldrich were used for thin-layer chromatography (0.25 and 0.5 mm layer thickness for analytical and preparative TLC, respectively) and visualized under short (254 nm) and long (366 nm) wavelength UV light or a spray reagent (H2SO4− AcOH−H2O, 1:20:4). Column chromatography (CC) was conducted using silica gel 60 (63–200, 40–63, or 2–25 μm particle size) or Sephadex LH-20 from Sigma-Aldrich (Saint Louis, MO, USA).
The bioassays were performed inside a laminar flow hood, brand NuAire (Playmouth, MN, USA), class II, type A2. The cells were kept inside a CO2 incubator with a water jacket and HEPA filter, brand NuAire.
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