For the covalent modification of an HOPG surface, we used electrochemical grafting of diazonium salt derivatives: 4-nitrobenzenediazonium tetrafluoroborate (Sigma-Aldrich, >97%) and 3,5-dimethyl-4-nitrobenzenediazonium tetrafluoroborate, synthesized by us (see section S1 for synthesis procedure and characterization). For the noncovalent case, we used PPD molecules (Sigma-Aldrich, >99%) in 1,2,4-trichlorobenzene solvent (Sigma-Aldrich, anhydrous, >99.0%). The electrolyte solutions for grafting and for the electroreduction of nitro group to amine group were prepared from the following: (i) tetrabutylammonium hexafluorophosphate (TBA-PF6; Sigma-Aldrich, ≥99.0%) in acetonitrile (AcN; Fisher Chemical, HPLC grade) and (ii) potassium chloride (Alfa Aesar, 99.995%) in the mixture of water (Milli-Q, 18.2 megohm⋅cm) and ethanol (EtOH, absolute, p.a.). To have a clean electrode surface, the top layers of the HOPG electrode were peeled out with a Scotch tape before the experiments.
4 nitrobenzenediazonium tetrafluoroborate
Manufactured by Merck Group
4-nitrobenzenediazonium tetrafluoroborate is a chemical compound used as a reagent in organic synthesis. It is a diazonium salt that can be used for various organic reactions, such as diazo coupling reactions. The core function of this product is to serve as a reactive intermediate in chemical transformations.
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Lab products found in correlation
Tetrabutylammonium hexafluorophosphate tbapf6, by Merck Group (1 mentions)
Sodium nitrite, by Thermo Fisher Scientific (1 mentions)
1 m hydrochloric acid solution, by Merck Group (1 mentions)
M toluidine, by Merck Group (1 mentions)
Anhydrous dichloromethane, by Merck Group (1 mentions)
Nickel 2 acetylacetonate, by Merck Group (1 mentions)
Nitrosyl tetrafluoroborate, by Merck Group (1 mentions)
4 methoxybenzenediazonium tetrafluoroborate, by Merck Group (1 mentions)
Anhydrous acetone, by Merck Group (1 mentions)
Milliq uf plus system, by Merck Group (1 mentions)
Iron 2 chloride tetrahydrate, by Merck Group (1 mentions)
Copper 2 chloride, by Merck Group (1 mentions)
Cobalt 2 chloride, by Merck Group (1 mentions)
N n dimethylformamide (dmf), by Merck Group (1 mentions)
Acetonitrile, by Merck Group (1 mentions)
Diethyl ether, by Merck Group (1 mentions)
Sodium nitrite, by Merck Group (1 mentions)
Nitrobenzene, by Merck Group (1 mentions)
4 tert butyl aniline, by Merck Group (1 mentions)
Sodium tetrafluoroborate, by Merck Group (1 mentions)
6 protocols using 4 nitrobenzenediazonium tetrafluoroborate
1
Covalent and Noncovalent Modification of HOPG
2
Diazonium-Based Surface Grafting
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Grafting solutions were prepared from 4-nitrobenzenediazonium tetrafluoroborate (Sigma Aldrich, 96%) dissolved in Milli-Q water (18.2 MΩ cm -1 ), the pH of which was adjusted to 2 using a 1 M hydrochloric acid solution (Sigma Aldrich). Solutions containing (2,2,6,6-tetramethylpiperidin-1-yl)oxy (Sigma Aldrich) were prepared in a 1 : 1 solvent mixture of Milli-Q water at pH 2 and dimethylsulfoxide (Carlo Erba Reagents). m-Methyl-diazonium chloride used in control experiments was prepared from m-toluidine (99%, Sigma Aldrich) using sodium nitrite (Acros Organics) aqueous solution ( pH 2) at stoichiometric proportions. All commercial chemicals were used without further purification.
3
Synthesis and Characterization of Functionalized Aryldiazonium Salts
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Nickel(II) acetylacetonate [Ni(C5H7O2)2], anhydrous tert‐butanol [(CH3)3COH], potassium hydroxide (KOH), 4‐nitrobenzenediazonium tetrafluoroborate (C6H4N3O2BF4), 3,5‐dichlorophenyldiazonium tetrafluoroborate (C6H3Cl2N2BF4), 4‐methoxybenzenediazonium tetrafluoroborate (CH3OC6H4N2BF4), 2,3,4,5,6‐pentafluoroaniline (C6F5NH2), nitrosyl tetrafluoroborate (NOBF4), anhydrous acetone (CH3COCH3), anhydrous dichloromethane (CH2Cl2), and acetonitrile‐d3(CD3CN) were purchased from Sigma‐Aldrich. 4‐carboxylbenzenediazonium tetrafluoroborate (CO2HC6H4N2BF4) was purchased from Chemtronica AB (Sweden). The water used for electrolyte solutions was deionized using a Millipore Milli‐Q UF Plus system (15–18 MΩ‐cm resistivity).
4
Synthesis of Molybdenum Disulfide Composites
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All organic solvents were
high-performance liquid chromatography (HPLC)-grade and used without
further purification. Bulk molybdenum disulfide powder (from ∼6
μm to a maximum of 40 μm, 98%, product number 69860, batch
number WXBD2352V) was purchased from Sigma-Aldrich and used without
further purification. Iron(II) chloride tetrahydrate, cobalt(II) chloride,
zinc(II) chloride, and copper(II) chloride were purchased from Sigma-Aldrich.
4-nitrobenzenediazonium tetrafluoroborate (97%), sodium tetrafluoroborate
(98%), sodium nitrite (reagent plus, ≥99%), nitrobenzene (≥99%),
1,2-dichlorobenzene (anhydrous, 99%), isopentyl nitrite (96%), acetonitrile
(HPLC gradient grade, ≥99.9%), N,N-dimethylformamide (≥99.8%), diethyl ether (HPLC, ≥99.9%,
inhibitor-free), Whatman poly(tetrafluoroethylene) (PTFE) membrane
filters (PTFE membrane circles, TE 36, 0.45 μm, 47 mm), and
4-tert-butylaniline (99%) were purchased from Sigma-Aldrich.
Water used for experiments was ultrapure type I water (18.2 MΩ
cm) from a Millipore Simplicity water purification system.
high-performance liquid chromatography (HPLC)-grade and used without
further purification. Bulk molybdenum disulfide powder (from ∼6
μm to a maximum of 40 μm, 98%, product number 69860, batch
number WXBD2352V) was purchased from Sigma-Aldrich and used without
further purification. Iron(II) chloride tetrahydrate, cobalt(II) chloride,
zinc(II) chloride, and copper(II) chloride were purchased from Sigma-Aldrich.
4-nitrobenzenediazonium tetrafluoroborate (97%), sodium tetrafluoroborate
(98%), sodium nitrite (reagent plus, ≥99%), nitrobenzene (≥99%),
1,2-dichlorobenzene (anhydrous, 99%), isopentyl nitrite (96%), acetonitrile
(HPLC gradient grade, ≥99.9%), N,N-dimethylformamide (≥99.8%), diethyl ether (HPLC, ≥99.9%,
inhibitor-free), Whatman poly(tetrafluoroethylene) (PTFE) membrane
filters (PTFE membrane circles, TE 36, 0.45 μm, 47 mm), and
4-tert-butylaniline (99%) were purchased from Sigma-Aldrich.
Water used for experiments was ultrapure type I water (18.2 MΩ
cm) from a Millipore Simplicity water purification system.
5
Resin-Bound Peptide Modification
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To a portion of resin-bound peptide (appx. 20 mg) in 900 µL of 100 mM phosphate buffer, pH 9.0 was added 100 µL of a saturated solution of 4-nitrobenzenediazonium tetrafluoroborate (300 mM, Sigma-Aldrich) in MeCN at 4°C. After rotation for 30 min at 4°C, the resin was rinsed with MeCN and DMF until no color remained in solution. The peptides were then cleaved from the resin, and the modification was confirmed by MALDI-TOF MS (Figures S1 –S2 ).
6
Diazotization of 4-Aminobenzoic Acid
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2.1. Reagents 4-Aminobenzoic acid, 4-nitrobenzenediazonium tetrafluoroborate, tetrabutylammonium tetrafluoroborate, 2,2'-azobis(3-ethylbenzothiazole-6-sulfonic acid) (ABTS), toluidine blue-O (TBO) and N-hydroxysuccinimide (NHS) were purchased from Sigma-Aldrich. 2-1-(3dimethylaminopropyl)-3-ethylcarbodiimide (EDC) was from Fluka. Buffer solutions were prepared with disodium hydrogenophosphate (Acros Organics), sodium dihydrogenophosphate, sodium acetate and acetic acid (Prolabo) in deionized water (Milli-Q grade, Millipore). Sodium perchlorate (Sigma-Aldrich) was used as electrolyte.
Diazotation of 4-Aminobenzoic acid 4 mL of tetrafluoroboric acid was cooled in an ice bath to 5°C before adding 4.10 -3 mole of 4aminobenzoic acid. Following the addition, the temperature of the solution was maintained at 5°C for 20 minutes. A yellow precipitate formed during the slow addition of 4.5 10 -3 moles of sodium nitrite. The diazonium salt was succion filtered and washed with cold ether. The solid was then dissolved in less than 5 mL methanol and crystallized by ether addition.
Diazotation of 4-Aminobenzoic acid 4 mL of tetrafluoroboric acid was cooled in an ice bath to 5°C before adding 4.10 -3 mole of 4aminobenzoic acid. Following the addition, the temperature of the solution was maintained at 5°C for 20 minutes. A yellow precipitate formed during the slow addition of 4.5 10 -3 moles of sodium nitrite. The diazonium salt was succion filtered and washed with cold ether. The solid was then dissolved in less than 5 mL methanol and crystallized by ether addition.
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