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17 protocols using 1 6 dibromohexane

1

AEM Electrolyzer Catalyst Fabrication

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SEBS (30 wt% styrene, Taipol 6152) was provided by TSRC cooperation. Commercial catalysts H2GEN-M (which contains Mo and C) and OXYGN-N (which mainly contains Ni and Fe) from CENmat were used for fabrication of the cathode and anode, respectively, for the AEM electrolyzer tests. These catalysts are platinum group metal (PGM)free. Chlorotrimethylsilane, 1,3-dibromopropane, 1,4-dibromobutane, sodium chloride, and potassium hydroxide were purchased from TCI Europe. Trioxane, tin (IV) chloride, 1,6-dibromohexane, chloroform, xylene, dimethyl sulfoxide, water solution of trimethylamine (33%), ethanol, dichloromethane, and tetrahydrofuran were all purchased from Merck. All chemicals were used as received without further purification.
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2

Synthesis of Thiophene Derivatives

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Analytical grade ferric chloride, ferrous chloride, ammonia solution (25 wt %), thiophene, 4-hydroxybenzaldehyde, acetonitrile, potassium permanganate, 4-aminophenol, 3-bromothiophene, 1,6-dibromohexane, N-bromosuccinimide, acetic acid, sodium hydrogen bicarbonate, potassium iodide, potassium carbonate, tetrahydrofuran, methanol, hydrochloric acid, acetone and ethyl acetate were purchased from Merck (Darmstadt, Germany). acetone was procured from Fisher Scientific (Loughborough, UK). thiophene carboxaldehyde, polyvinyl alcohol and n-butyllithium (2.0 M in cyclohexane) were obtained from Sigma Aldrich (Milwaukee, WI, USA). Magnesium sulfate anhydrous, ethanol denatured and hexane were received from J. Kollins (Parkwood, Australia), while dimethyl sulfoxide-d6 (DMSO-d6) and phthalate esters were purchased from Acros Organics (Geel, Belgium). Ultrapure water was prepared by a model Aqua Max-Ultra ultra-pure water purification system (Zef Scientific Inc., San Diego, CA, USA). Stock solutions of 1000 mg·L−1 of standards were prepared by dissolving appropriate amounts of compounds in methanol, which remain stable for three months if stored in a refrigerator at 4 °C. Working standard solutions were prepared daily by diluting the stock standard solution to the required concentrations.
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3

Corrosion Inhibitor Synthesis and Testing

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The API X60 pipe
from which samples used in this work were made from
was obtained from the oil and gas industry in Saudi Arabia. The elemental
composition of the X60 steel is as given in Onyeachu et al.,39 (link) and the sample pretreatment process was as detailed
in the ASTM G1-03.54 The sample surfaces
were abraded to a final 800-grit size using silicon carbide paper.
The chemicals used for the synthesis of the studied inhibitors
were procured from Merck Schuchardt OHG and include diallylamine (99%;
CAS-No: 124-02-7), 1,6-dibromohexane (96%; CAS-No: 629-03-8), 2,2′-azobis(2-methylpropionamidine)dihydrochloride
(AMPD) (97%; CAS-No: 2997-92-4), and tripropyl amine. They were used
as purchased without further purification.
The corrosive medium
was 15 wt % HCl solution prepared by diluting
concentrated hydrochloric acid (37%; purchased from Merck) with distilled
water.
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4

Synthesis and Characterization of Amphiphilic Compounds

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The following chemicals
were purchased from Sigma-Aldrich (Poznan, Poland): 1,6-dibromohexane
(purity 96%), 1,8-dibromooctane (purity 98%), 1,12-dibromododecane
(purity 98%), dimethyloctylamine (purity 97%), decyldimethylamine
(purity 90%), dimethyldodecylamine (purity 97%), dimethyltetradecylamine
(purity 95%), hexadecyldimethylamine (purity 95%), l-tryptophan
(purity 98%), and Dowex-Monosphere 550A anion exchange resin. (4-Chloro-2-methylphenoxy)acetic
acid [MCPA] (purity 97%) was obtained from CIECH Sarzyna (Nowa Sarzyna,
Poland). All solvents (methanol, acetonitrile, acetone, hexane, toluene,
chloroform, isopropanol, DMSO, and ethyl acetate) were from Avantor
(Gliwice, Poland). Deionized water with conductivity <0.1 μS·cm–1, from demineralizer HLP Smart 1000 (Hydrolab, Poland),
was used for solubility and surface activity measurement. All reagents
and solvents were used without further purification. As a reference,
Chwastox Extra 300 SL (300 g MCPA per 1 L, CIECH Sarzyna, Poland)
was used as a commercial herbicide. Microbiological media used for
the studies were purchased in BioMaxima (Poland).
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5

Synthesis of Halogenated Monomers

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1,2-Dibromeoethane (99%), 1,3-dibromopropane (99%), 1,4-dibromobutane (99%), 1,5-dibromopentane (97%), 1,6-dibromohexane (98%), 1,7-dibromopentane (97%), 1,8-dibromooctane (98%), hydroquinone (99%), sodium hydrosulfite (technical grade), sodium sulfite (98%), 3-chloroperbenzoic acid (≤77%), thionyl chloride (99%), allyl bromide (99%), 4-hydroxybezoic acid (99%), and pyridine (anhydrous, 99.8%) were purchased from Sigma Aldrich and used without further purification. Sodium bicarbonate (99%), magnesium sulfate anhydrous (99%), sodium chloride (99%), hexanes (98.5%), ethyl acetate (99.5%) and ethyl ether anhydrous (99%), and methanol (ACS grade) were purchased from Fisher Chemical and used without further purification. Chloroform (HPLC grade), methylene chloride (HPLC), and acetonitrile (anhydrous), was purchased from Fisher Chemical and stored with activated molecular sieves to remove water. Sodium sulfate anhydrous (99%) and potassium hydroxide (85%) were purchased from Oakwood Chemical and used without further purification. Hydrochloric acid (10M) was purchased from Ricca Chemical and used without further purification. Sulfuric acid (95%) was purchases from VWR analytical and used without further purification. Ethanol anhydrous (99.9%) was purchased from Decon and used without further purification. Synthesis details of Cx diepoxy monomer is shown in SI Appendix.
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6

Synthesis of Functionalized Fluorene Derivatives

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Sodium-exchanged Somasif ME100 (SME, CO-OP Chemicals, CEC = 1.2 mmol·g−1) was dried at 130 °C under reduced pressure (10−3 bar) for 2 weeks and then it was stored under nitrogen. Ethyl alcohol (Carlo Erba, 96% pure) was degassed under vacuum then by bubbling nitrogen, kept over molecular sieves and used without any further purification. Styrene (Aldrich, 99% pure) was refluxed for 4 h over CaH2, then distilled trap-to-trap and stored under nitrogen. Distilled deionized water was used for all ion-exchange experiments. 2,7-dibromofluorene, 1,6-dibromohexane and trimethylamine were purchased from Sigma–Aldrich. 9,9-di-n-octylfluorene-2-boronic acid pinacol ester was purchased from Alfa Aesar. 2,7-dibromo-9,9-bis(6’-bromohexyl)fluorene was synthesized following the procedure reported elsewhere [36 (link)].
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7

Multi-Ingredient Formulation Protocol

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Glycoluril, hydrochloric acid (37%), 1,6-dibromohexane, deuterium oxide (99.9%), deuterium chloride (35%), isoquinoline and chlorocresol (4-chloro-3-methyphenol) were purchased from Sigma-Aldrich. Paraformaldehyde was purchased from AlfaAesar. Phenoxyethanol, zinc oxide BP, lanolin anhydrous and citric acid monohydrate were purchased from the Sydney Essential Oil Company. Cetostearyl alcohol was purchased from Bronson and Jacobs. White soft paraffin was supplied by The University of Sydney Dispensing Laboratory. Sodium phosphate BP was purchased from the Government Store Department. 1,4-dioxane, calcium hydroxide solution and sulfuric acid were purchased from Merck. Arachis oil was purchased from Proteco and oleic acid from Professional Compounding Chemists of Australia. All water was obtained from an SG ultra clear water system. Phosphate buffered saline (PBS) solutions were made using pure water and PBS tablets from Sigma Life Sciences. All other chemicals including: methanol, ethanol and diethyl ether, were of analytical reagent grade.
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8

Polymer and Nanoparticle Synthesis Protocols

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Chemicals used for polymer and nanoparticle synthesis: 4-p-hydroxybenzoic acid, tri-ethylene-glycol, 1,6-dibromohexane were obtained from Sigma Aldrich (St. Louis, MO); dimethyl formamide, acetic acid, acetonitrile, acetic anhydride, toluene, methylene chloride, pentane were purchased from Fisher Scientific (Fairlawn, NJ). 4-p-flourobenzonitrile was purchased from Apollo Scientific (Cheshire, UK). Dithio-RP,RP-cyclic di-guanosine monophosphate (R,R-Cyclic di-GMP (CDG)) was kindly provided by Aduro Biotech (Berkeley, CA).
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9

Polymer and Nanoparticle Synthesis Protocol

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Chemicals used for the polymer and nanoparticle synthesis, 4-p-hydroxybenzoic acid, tri-ethylene-glycol, and 1,6-dibromohexane were obtained from Sigma Aldrich (St. Louis, MO); dimethylformamide, acetic acid, acetonitrile, acetic anhydride, toluene, methylene chloride, pentane were purchased from Fisher Scientific (Fairlawn, NJ) and 4-p-flourobenzonitrile was purchased from Apollo Scientific (Cheshire, UK).
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10

Synthesis of CPTEG and CPH Polymers

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Chemicals used for CPTEG and CPH diacid and polymer synthesis included 1,6-dibromohexane, triethylene 4-p-hydroxybenzoic acid, and 1-methyl-2-pyrrolidinone, purchased from Sigma-Aldrich (St. Louis, MO). Chloroform, petroleum ether, ethyl ether, hexanes, sodium hydroxide, toluene, sulfuric acid, acetonitrile, dimethyl formamide, acetic anhydride, methylene chloride, pentane, and potassium carbonate were purchased from Fisher Scientific (Fairlawn, NJ). 4-p-fluorobenzonitrile was purchased from Apollo Scientific (Cheshire, UK). Deuterated Chloroform used for 1H NMR analysis was purchased from Cambridge Isotope Laboratories (Andover, MA). Dithio-RP,RP-cyclic di-guanosine monophosphate (R,R-Cyclic di-GMP (CDG)) was provided by Aduro Biotech (Berkeley, CA). Complete cell culture medium reagents RPMI 1640 and penicillin-streptomycin were purchased from Mediatech (Herndon, VA); heat inactivated fetal calf serum was purchased from Atlanta Biologicals (Atlanta, GA). Y. pestis, strain CO92 (NR-641) and the Y. pestis fusion protein F1-V (NR-4526) were obtained from the Biodefense and Emerging Infections Repository (Manassas, VA).
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