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11 protocols using benzyl chloride

1

Synthesis and Characterization of Organometallic Catalysts

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Benzyl chloride (99%, containing propylene oxide as stabilizer), methanol, chloroform, tetrahydrofuran (THF) ( 99.9% HPLC LiChrosol), 2-butanone and toluene were all purchased from Sigma-Aldrich (Buchs, Switzerland). The catalysts [WCl4(THF)2], [WCl4(MeCN)2], [WBr2(CO)3(dme)] and [MoI2(CO)3(MeCN)2] used in this article and displayed in Figure 2 were stored under inert gas atmosphere before use (for synthesis, see Supplementary Materials).
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2

Synthesis of Colloidal Nanocrystals

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Hafnium(IV) chloride (98%), zirconium(IV)
chloride (≥99.5%), oleic acid (90%), oleylamine (70%), trimethyl
orthoformate (99%), trifluoroacetic acid (99%), acetic acid (≥99%),
dibenzyl ether (98%), and benzyl chloride (99%) are obtained from
Sigma-Aldrich. Benzyl alcohol was purchased either anydrous (99.8%)
or as ReagentPlus (≥99%) from Sigma-Aldrich; the latter was
then vacuum distilled and stored over sieves. Tetrahydrofuran (extra
dry, 99.5%) was purchased from Acros Organics. Hydrochloric acid (≥37%)
was purchased from Chemlab. Tri-n-octylphosphine
oxide (99%) was puchased from Strem chemicals and recrystallized according
to Owen et al.81 (link) Solvents used for synthesis
were purchased from Chemlab or Sigma-Aldrich. Deuterated solvents
(CDCl3 and C6D6) were purchased from
Sigma-Aldrich or Eurisotop.
All manipulations were performed
in air, unless otherwise indicated. All chemicals are used as received
unless otherwise mentioned. When required, organic solvents are dried
according to the procedure described by Williams et al.82 (link) making use of 20% m/v freshly activated 3 Å
sieves for a minimum of 120 h.
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3

Synthesis and Characterization of Hybrid Nanomaterials

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Iso-propanol (i-PrOH, 99.5%, anhydrous), phenylselenyl bromide (PhSeBr, 98%), D-tartaric acid (DTA, 98%), D-lactic acid (DLA, 98%), 1,2,3,4,5-pentafluoro-6-iodobenzene (PFIB, 98%), 1,4-diiodotetrafluorobenzene (DIFB, 98%), dimethylsulfate (DMS, 99%), benzyl chloride (BC, 98%), copper acetate (Cu2+, 98%) and Karstedt’s catalyst (Pt(0), 2% Pt in xylene) were purchased from Sigma-Aldrich. All other reagents were used as received, unless mentioned elsewhere. The diblock copolymer P2VP68-b-PFMA41 (P2VP = poly(2-vinyl pyridine), PFMA = poly(2-(perfluorooctyl)ethyl methacrylate, the subscripts represent the numbers of repeating units) was synthesized via sequential anionic polymerization30 (link). Carbon nanotubes with hydroxyl surface groups (CNTs, multi-walled, the inside diameter of 5–12 nm and the outside diameter of 30–50 nm) was purchased from Sigma-Aldrich. Graphene oxide nanosheets (GOs) was purchased from Tanfeng Tech. Inc. Carboxyl-decorated polystyrene spheres (NSs, diameter of 90 nm) were purchased from BaseLine Chrom. Tech. Research Centre. The CNTs, GOs, and NSs solution (1.0 mg/mL, i-PrOH) were dispersed via sonication (50 W sonication processor equipped with a titanium sonotrode) at 0 °C for 15 min before use.
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4

Synthetic Reagent Preparation Protocol

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Chemicals were purchased from the following companies: Dichloromethane (99 + %), chloroform (99.8%), pentane (99.0%), decalin (98%, cis and trans), methanol (99.8%), benzyl chloride (99%) and SnCl4 (99%) from Sigma-Aldrich (Buchs, St.Gallen, Switzerland); AgSO3CF3 (99%) from Fluorochem (Hadfield, Glossop, UK); AgClO4 (97%) and [Cr(CO)6] (99%) from ABCR (Kasru, Baden-Wuerttemberg, Germany); and dry THF (99.5%) over a molecular sieve from Fisher Scientific (Schwerte, Nordrhein-Westfalen, Germany). All chemicals were used as received.
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5

Synthesis of Pyrazolone Derivatives

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All reactions were carried out in air unless otherwise stated. All solvents used were reagent grade, purchased from Sigma Aldrich and dried under nitrogen before use. 4-(Chloromethyl)benzoic acid, thionyl chloride, 1,3-diphenyl-1,3-propanedione, hydrazine monohydrate, sodium hydride, 2,2,6,6-tetramethyl-3,5-heptanedione, potassium hydroxide, benzyl bromide, benzyl chloride, sodium hydroxide, sodium bicarbonate, potassium tert-butoxide, ethyl acetate and glacial acetic acid were purchased from Sigma Aldrich and used without further purification. PdCl2 was purchased from Heraeus South Africa and used as received. [PdCl2(MeCN)2],22 3,5-di-tert-butylpyrazole,23 (link) 3,5-diphenylpyrazole24 (link) and methyl-4-(chloromethyl)benzoate25 (link) were synthesized according to literature procedures.
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6

Synthesis and Characterization of Ionic Liquids

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1-butylimidazole (98%, Sigma-Aldrich), 1-chloropentane (99%, Sigma-Aldrich), potassium trifluoromethanesulfonate (KOTf, Sigma-Aldrich), sodium tetrafluoroborate (NaBF4, Sigma-Aldrich), benzyl chloride (99%, Sigma-Aldrich), dimethyl sulfoxide-D6 (DMSO‑d6, 99.9%) + 0.05% V/V tetramethylsilane (TMS, Cambridge Isotope Laboratories, Inc.), NH3 (99.99%), Ar gas (99.99%), and ethyl acetate (99.5%, Sigma-Aldrich) (Table 1) were used as received without any purification.

Materials for IL synthesis and characterization.

Table 1
MaterialsMolecular formulaCAS NumberPurityCompany
1-butylimidazoleC7H12N24316-42-198%Sigma-Aldrich
1-chloropentaneC5H11Cl543-59-999%
Potassium trifluoromethanesulfonateCF3KO3S2926-27-498%
Sodium tetrafluoroborateNaBF413755-29-898%
ethyl acetateC4H8O2141-78-699.5%
Dimethyl sulfoxide-D6+0.05% V/V tetramethylsilaneC2H6OS + Si(CH3)42206-27-199.9%Cambridge Isotope Laboratories, Inc.
AmmoniaNH399.9%
ArgonAr99.9%
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7

Fabrication of Nanomaterials via Solvent-Assisted Assembly

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Cetyltrimethylammonium chloride (CTAC), triethanolamine (TEA), 1H,1H,2H, 2H-perfluorodecanethiol, pyridine, benzyl chloride, and cyclohexane were purchased from Sigma-Aldrich Corp. Sodium chloride, sodium hydroxide, tetraethyl orthosilicate (TEOS), methanol ethanol, bovine serum albumin (BSA) proline, mannitol, lysine, and sucrose were purchased from Adamas Reagent Ltd. All the above chemicals were used as received without further purification. ITO slides were purchased from Luoyang Guluo Glass Co., Ltd. These ITO slides were first treated with NaOH solution (2 M) at room temperature for 12 h to clean the organic residues and then stored in deionized water for the subsequent experiments. Gold sputtering material (99.99%) was purchased from Hefei Kejing Auto-instrument Co., Ltd, China. Deionized water (18.2 MΩ cm) was obtained by a Milli-Q system (Millipore, United States) and used for all experiments in this work.
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8

Synthesis and Characterization of Cadmium-based Nanostructures

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Cadmium oxide (Aldrich, 99.99%), sulphur (99.9% powder, Anachemia Chemicals Ltd.), selenium (Aldrich), tributylphosphine oxide (Aldrich), octadecylamine (Aldrich, ODA), zinc oxide (Alfa Aesar), ODE (1-octadecene, Aldrich, 90%), oleic acid (Aldrich), tri-n-octylphosphine (Aldrich), tributylphosphine (Aldrich, TBP), stearic acid (Aldrich, SA) and oleic acid (Aldrich, OA). To complete this research, the toxic chemicals such as 3,4-diaminotoluene, 3-chlorophenol, 3-methoxyphenol, 4-aminophenol, 4-nitrophenyhydrazine, acetonitrile, benzylchloride, chlorobenzene, p-nitrophenol and toluene were obtained from the sigma Aldrich supplier and used directly without any refinement. To execute the electrochemical investigation, a Keithly Electrometer was used to analyze into electrochemical cell by electrochemical investigation.
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9

Preparation and Characterization of Organofunctional Silane Coatings

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Benzyl chloride stabilized by propylene oxide (99%), bismuth (III) trifluoromethansulfunate (98%), thionyl chloride (99%), and chloroform (99.8%, amylene stabilized) were purchased from Sigma Aldrich (Buchs, Switzerland), benzyltriethoxysilane (96%) from Fluorochem (Hadfield, UK), 4-methoxybenzylchloride (99%) from Apollo Scientific Ltd. (Whitefield, UK) and methanol (98%) from Merck (Darmstadt, Germany). Aluminum alloy AA2024 panels 4.5 cm in length, 3 cm in width and 5 mm in thickness (4.3–4.5% copper, 1.3–1.5% magnesium, 0.5–0.6% manganese, and less than 0.5% of other elements) were provided by Aviometal s.p.a. (Varese, Italy).
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10

Benzyl chloride oxidation protocol

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Benzyl chloride (99%), N,N,N,N-tetramethyl-1,3-propanediamine, and H2O2 (50 wt%) were obtained from Sigma Aldrich. Ethyl alcohol and acetonitrile (HPLC grade) were obtained from Morgan and Merck chemicals, respectively. All chemicals were of analytical grade and were used directly without further treatments. Gas oil was collected from Cairo oil refining company, Egypt.
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