Cyclic voltammetry and electrochemical impedance spectroscopy (EIS) was performed with a Biologic VSP multichannel potentiostat/galvanostat. Cyclic voltammetry was carried out in a three-electrode electrochemical cell, consisting of a glassy carbon disk working electrode (0.07 cm2, BASi), an Ag/Ag+ quasi-reference electrode (BASi) with 0.01 M AgBF4 (Sigma) in MeCN, and a platinum wire counter electrode (23 cm, ALS). The glassy carbon disk electrode was polished in a nitrogen-filled glovebox using diamond polish (15 µm, BASi) and anhydrous MeCN. All experiments were performed at a scan rate of 100 mV/s in a MeCN electrolyte containing 0.1 M KPF6 unless otherwise noted. Reference electrodes were calibrated against an internal voltage reference of ferrocene (1–10 mM). Reactions were conducted as two-electrode cells with a LANHE LAND battery testing system using nickel foam (1.5 mm × 250 mm × 200 mm, 110 ppi, 99.8% purity, purchased from Amazon.com) and RVC electrodes (purchased from ERG Aerospace).
Agbf4
Manufactured by Merck Group
Sourced in United States
AgBF4 is a chemical compound that serves as a salt. It consists of a silver cation (Ag+) and a tetrafluoroborate anion (BF4-). This product is used in various laboratory applications, but a detailed description of its intended use is not available while maintaining an unbiased and factual approach.
Automatically generated - may contain errors
Lab products found in correlation
Agotf, by Merck Group (2 mentions)
Ch2cl2, by Avantor (1 mentions)
Lintf2, by Merck Group (1 mentions)
Nabf4, by Merck Group (1 mentions)
Dichloromethane dcm, by Merck Group (1 mentions)
300 mhz spectrometer, by Bruker (1 mentions)
Tlc silica gel 60 f254 plate, by Merck Group (1 mentions)
Haucl4 3h2o, by Merck Group (1 mentions)
Nabh4, by Merck Group (1 mentions)
Merck silica gel 60 f254, by Merck Group (1 mentions)
Spectrum one spectrophotometer, by PerkinElmer (1 mentions)
Geduran si 60 silicagel, by Merck Group (1 mentions)
Ph3p aucl, by Merck Group (1 mentions)
Avance 300, by Bruker (1 mentions)
Agcf3so3, by Merck Group (1 mentions)
Ethanol, by Merck Group (1 mentions)
Methanol, by Merck Group (1 mentions)
Agno3, by Merck Group (1 mentions)
6 protocols using agbf4
1
Electrochemical Characterization of Energy Materials
2
Synthesis of Cy3 Anion Complexes
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Experiments were carried out in air unless otherwise stated. Cy3 iodide was purchased from TCI and used as received. The metal salts LiNTf2, AgOTf, KPF6, NaBF4 and AgBF4 were purchased from Sigma Aldrich and used as received. NaCHTf2 was synthesized according to the procedure of Waller et al.24 (link) MeOH, Et2O (both HPLC grade) and CH2Cl2 were purchased from VWR and used as received.
For the metathesis of Cy3 anions, Cy3 iodide was dissolved in a suitable solvent. Solid metal salt was added and the reaction stirred at RT for 2–4 days. After this time the reaction was filtered and volatiles were removed in vacuo, affording solid [Cy3][X] (X = NTf2, OTf, PF6, BF4, or CHTf2), which was recrystallised from a suitable solvent.
Full synthetic procedures, characterisation and yields are presented in the ESI Section S2.†
For the metathesis of Cy3 anions, Cy3 iodide was dissolved in a suitable solvent. Solid metal salt was added and the reaction stirred at RT for 2–4 days. After this time the reaction was filtered and volatiles were removed in vacuo, affording solid [Cy3][X] (X = NTf2, OTf, PF6, BF4, or CHTf2), which was recrystallised from a suitable solvent.
Full synthetic procedures, characterisation and yields are presented in the ESI Section S2.
3
Ethylation and Methylation of Dibenzothiophene
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DBT, DCE, AgBF4, anthracene (ANTH), dibenzofuran (DBF), acetic acid (AcOH) and dichloromethane (DCM) were purchased from Sigma-Aldrich (high purity, St. Louis, MO, USA). C2H5I, acridine (ACR), CD3I and C2D5I were purchased from Sigma-Aldrich (high purity, Steinheim, Germany). A heavy crude oil of North American origin was used.
10 mg of DBT were dissolved in 1 mL anhydrous DCE. During mixing, a solution of 2 molar eq. AgBF4 (21.13 mg) in 0.5 mL DCE was added. After 2 min, 8 molar eqivalents (28 μL) of C2H5I was then added and yellow silver iodide precipitated immediately. After 4 h, the solid was removed by centrifugation and washed with 0.5 mL of DCE. A final concentration of 500 μg/mL of the ethylated DBT was obtained through dilution with DCM; the procedure above was successively applied to a mixture of standard compounds: 6.5 mg of ANTH, 2.75 mg of DBT, 0.25 mg of ACR, 0.5 mg of DBF. The same procedure was further employed to 10 mg of the heavy crude oil by replacing C2H5I with CD3I and C2D5I. For a comparison, a heavy crude oil sample with a final concentration of 500 μg/mL in DCE containing 0.2% AcOH was used for ESI analysis.
10 mg of DBT were dissolved in 1 mL anhydrous DCE. During mixing, a solution of 2 molar eq. AgBF4 (21.13 mg) in 0.5 mL DCE was added. After 2 min, 8 molar eqivalents (28 μL) of C2H5I was then added and yellow silver iodide precipitated immediately. After 4 h, the solid was removed by centrifugation and washed with 0.5 mL of DCE. A final concentration of 500 μg/mL of the ethylated DBT was obtained through dilution with DCM; the procedure above was successively applied to a mixture of standard compounds: 6.5 mg of ANTH, 2.75 mg of DBT, 0.25 mg of ACR, 0.5 mg of DBF. The same procedure was further employed to 10 mg of the heavy crude oil by replacing C2H5I with CD3I and C2D5I. For a comparison, a heavy crude oil sample with a final concentration of 500 μg/mL in DCE containing 0.2% AcOH was used for ESI analysis.
4
Synthesis and Characterization of AuNPs
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Reactions were performed using oven-dried glassware. Chemicals were obtained from Alfa-Aesar (HAuCl4.3H2O, benzimidazole, di-ndodecylsulfide, benzyl bromide), Sigma-Aldrich (AgBF4), Panreac (NaBH4) and Lancaster (tetra-n-octylammonium bromide), and used as received. The N,N-dibenzylbenzimidazolium bromide precursor, the AuNPs functionalized by di-n-dodecylsulfide, and complex 2c were synthesized as described in the supporting information. All reactions were monitored by thin-layer chromatography using Merck© TLC Silica gel 60 F254 plates. 1 H and 13 C{ 1 H} solution NMR spectra were recorded in DMSO-d6 on a Bruker 300 MHz spectrometer. Chemical shifts are reported in ppm, referenced to DMSO solvent residual peak at 2.50 ppm for 1 H, and 39.52 ppm for 13 C{ 1 H}. Abbreviations for 1 H NMR spectra used are as follows: s, singlet ; d, doublet; t, triplet; qt, quintuplet; m, multiplet. ESI mass spectra were recorded on a Q-Tof Waters 2001 MS spectrometer.
5
Gold(I) Catalyzed Organic Synthesis
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All reactions were carried out under argon atmosphere in dried glassware. Toluene and benzene were dried and freshly distilled from sodium. Acetonitrile was dried and freshly distilled from CaH2. (Ph3P)AuCl, AgOTf, AgBF4 and CuI were purchased from Sigma-Aldrich ® , in ≥99.9%, ≥99.95% and 98% purity respectively. (Ph3P)2PdCl2 was prepared from PdCl2 and PPh3.
Reactions were monitored by TLC with Merck ® Silica gel 60 F254. Purifications by flash chromatography were carried out using Merck ® Geduran ® Si 60 silica gel (40-63 µm). 1 H NMR spectra were recorded on a Bruker ® Avance 300 (300 MHz) NMR spectrometer, using CDCl3 as solvent. Data, reported using Me4Si (δH = 0.00 ppm) as internal reference, were as follows (in order): chemical shift (δ in ppm relative to Me4Si), multiplicity (s, d, t, q, m, br for singlet, doublet, triplet, quartet, multiplet, broad) and coupling constants (J in Hz). 13 C NMR was recorded at 75 MHz on the same instrument, using the CDCl3 solvent peak at (δC = 77.16 ppm) as reference. 19 F NMR was recorded at 282 MHz on the same instrument, using the CClF3 peak at (δF = 0.0 ppm) as internal reference. Mass spectra were obtained on a Hewlett Packard (engine 5988A) by direct inlet at 70eV. IR spectra were recorded on a Perkin-Elmer Spectrum One spectrophotometer. Melting points were uncorrected.
Reactions were monitored by TLC with Merck ® Silica gel 60 F254. Purifications by flash chromatography were carried out using Merck ® Geduran ® Si 60 silica gel (40-63 µm). 1 H NMR spectra were recorded on a Bruker ® Avance 300 (300 MHz) NMR spectrometer, using CDCl3 as solvent. Data, reported using Me4Si (δH = 0.00 ppm) as internal reference, were as follows (in order): chemical shift (δ in ppm relative to Me4Si), multiplicity (s, d, t, q, m, br for singlet, doublet, triplet, quartet, multiplet, broad) and coupling constants (J in Hz). 13 C NMR was recorded at 75 MHz on the same instrument, using the CDCl3 solvent peak at (δC = 77.16 ppm) as reference. 19 F NMR was recorded at 282 MHz on the same instrument, using the CClF3 peak at (δF = 0.0 ppm) as internal reference. Mass spectra were obtained on a Hewlett Packard (engine 5988A) by direct inlet at 70eV. IR spectra were recorded on a Perkin-Elmer Spectrum One spectrophotometer. Melting points were uncorrected.
6
Synthesis of Silver(I) Complexes
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Distilled water was demineralized and purified to a resistance of greater than 10 M/cm. The starting silver(I) salts (AgNO 3 , AgCF 3 SO 3 , AgClO 4 .
xH 2 O and AgBF 4 ), ethanol, methanol, acetonitrile and dimethyl sulfoxide were purchased from Sigma-Aldrich. Phthalazine (phtz) and quinazoline (qz) were obtained from ABCR. All reactants were of analytical reagent grade and used without further purification.
xH 2 O and AgBF 4 ), ethanol, methanol, acetonitrile and dimethyl sulfoxide were purchased from Sigma-Aldrich. Phthalazine (phtz) and quinazoline (qz) were obtained from ABCR. All reactants were of analytical reagent grade and used without further purification.
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