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11 protocols using orange 2

1

Synthesis of Organic Compounds

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Sodium hydroxide and ethanol were purchased from Merck KGaA (Darmstadt, Germany). Sodium chloride, hydrochloric acid, ethylenediamine (EDA), methylene blue, orange II, 1-bromooctane and 1-bromobutane were bought from Sigma Aldrich (St. Louis, MI, USA). Methyl iodide from VWR International (Radnor, PA, USA). All chemicals were used without any further purification.
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2

Synthesis and Characterization of 4

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Synthesis of 4 has recently been communicated.21 (link) Orange II was obtained from Sigma-Aldrich and purified by recrystallization. Hydrogen peroxide was obtained from Fisher Scientific and standardized using the absorbance at 230 nm.32 (link) All other reagents used in this study of at least ACS reagent grade were used as received.
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3

Azo Dye Degradation Assay

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Methyl Red, Sudan I, Sudan II, Sudan III, Sudan IV, Toluidine Red, Orange II, Fast Dark Blue R Salt, Lithol Rubin BK, Orange G, Amaranth, Ponceau BS, Direct Blue 15, and dimethyl sulfoxide (DMSO) were purchased from Sigma-Aldrich Inc. (Saint Louis, MO, USA). Solvent Red 1, Hansa Yellow, Hansa Orange, and Alphamine Red R were purchased from Fisher Scientific (Hanover Park, IL, USA). Diarylide Yellow HR (Pigment Yellow 83) was purchased from Santa Cruz Biotechnology Inc. (Dallas, TX, USA). Chemical structures of azo dyes used in this study were shown in Fig. 1. Tryptic Soy Agar (TSA) and Tryptic Soy Broth (TSB) used for bacterial growth were purchased from Fisher Scientific (Hanover Park, IL, USA). Stock solutions of azo dyes (10 mM) were prepared by using 100% DMSO as solvent, then dye solutions were diluted with TSB in degradation assay. Final concentration of DMSO and dye in the assays was 1% and 100 μM except as indicated otherwise.
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4

Azo Dye Degradation Assay

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Methyl Red, Sudan I, Sudan II, Sudan III, Sudan IV, Toluidine Red, Orange II, Fast Dark Blue R Salt, Lithol Rubin BK, Orange G, Amaranth, Ponceau BS, Direct Blue 15, and dimethyl sulfoxide (DMSO) were purchased from Sigma-Aldrich Inc. (Saint Louis, MO, USA). Solvent Red 1, Hansa Yellow, Hansa Orange, and Alphamine Red R were purchased from Fisher Scientific (Hanover Park, IL, USA). Diarylide Yellow HR (Pigment Yellow 83) was purchased from Santa Cruz Biotechnology Inc. (Dallas, TX, USA). Chemical structures of azo dyes used in this study were shown in Fig. 1. Tryptic Soy Agar (TSA) and Tryptic Soy Broth (TSB) used for bacterial growth were purchased from Fisher Scientific (Hanover Park, IL, USA). Stock solutions of azo dyes (10 mM) were prepared by using 100% DMSO as solvent, then dye solutions were diluted with TSB in degradation assay. Final concentration of DMSO and dye in the assays was 1% and 100 μM except as indicated otherwise.
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5

Titanium Oxide Synthesis Protocol

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All of the reagents used in this work were of analytical grade and were used with no further purification and are as follows: titanium(IV) isopropoxide (TTIP) (Aldrich, 97%); ethanol absolute grade (99.9%); hydrochloric acid (37%) and Orange II (Sigma Chemical Co.).
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6

Cellulose Nanofiltration Membranes from Ionic Liquids

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Cellulose (Baikal Cellulose and Paper Mill, Baikalsk, Russia) had a polymerization degree of 600 and contained 92% alpha-cellulose and less than 6% water. [EMIM]Ac, [EMIM]Cl, and [BMIM]Ac (Sigma-Aldrich, Steinheim, Germany) were used as ionic solvents, which were diluted with DMSO (Sigma-Aldrich) as a nominal co-solvent of cellulose. Non-woven polyester fabric (Crane Technical Materials, Pittsfield, MA, USA), which had a density of 87 g/m2, a thickness of 90–99 μm, and an air permeability of 16.0–29.6 cm·s−1·Pa−1, was used as a micro-porous substrate for impregnating with cellulose solution and subsequent production of cellulose nanofiltration membranes. Distilled water, methanol, ethanol, and isopropanol (Himmed, Moscow, Russia) were used as non-solvents (precipitants), while hexane (Himmed) was applied for the post-processing of formed membranes. The transport properties of obtained cellulose membranes were investigated by using DMF (Sigma-Aldrich) with dissolved dyes Orange II (350 g/mol, Sigma-Aldrich) and Remazol Brilliant Blue R (626 g/mol, Sigma-Aldrich). All reagents were chemically pure and used without additional purification.
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7

Dosing Graphene Samples with Purified Gases

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2-aminothiophenol (2-ATP; Sigma Aldrich, purity, 99.5%) and nitrobenzene (NB; Sigma Aldrich, purity, 99.0%), Orange II (Sigma Aldrich, purity, 99.5%), methylene blue (Sigma Aldrich, purity, 99.5%), carbon monoxide (CO, 99.95%) and molecular oxygen (O2, 99.99%) gas were purified by turbo-pumping to remove impurities prior to dosing onto the GO, rGO, and graphene samples grown on silicon substrates. A direct dozer, controlled by using a variable leak valve, was used to dose the substrates.
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8

Synthesis of Metal-Doped Photocatalysts

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All
the chemicals used
in this study were commercially available and used as supplied without
further purification. Aluminum nitrate nonahydrate, methyl orange,
and orange II were purchased from Sigma Aldrich, nickel nitrate hexahydrate
from THOMAS BAKER, titanium tetrachloride from LOBA CHEMIA, and tetracycline
hydrochloride from SRL. All other chemicals were procured from commercial
suppliers.
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9

Analytical Standards for Mass Spectrometry

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Optima LC/MS grade acetonitrile and water were purchased from Thermo Fisher Scientific (Pittsburgh, PA, USA). Sudan III [1-(4-(phenylazo)phenylazo)-2-naphthol] and Orange II [4-(2-hydroxy-1-naphthylazo) benzenesulfonic acid sodium salt], dimethylsulfoxide (DMSO), formic acid, leucine-enkephalin, L-tryptophan, and all MS standards were obtained from Sigma-Aldrich Corporation (St. Louis, MO, USA).
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10

Oxidative Degradation of Orange II

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Sodium acetate (99%), KH2PO4 (ACS reagent, ≥99.0%), reagent grade NaOCl solution
(available chlorine, 10–15%), and Orange II (certified) were
purchased from Sigma-Aldrich. Acetic acid (glacial), Na2HPO4 (anhydrous, enzyme grade), and water (HPLC grade,
submicrometer-filtered) were obtained from Fisher Scientific. Na3PO4·12H2O was purchased from Acros
Organics. Hydrogen peroxide (30%) stabilized by sodium stannate was
obtained from VWR Chemicals. Fe-TAML 2 synthesized as
previously described3 (link) was provided by SUDOC.23 Complexes 1a and 1b were obtained from old stocks at IGS (Institute of Green Science).
All the Fe-TAMLs used for kinetic measurements were purified by passing
through C-18 silica gel with water as an eluent. Orange II was recrystallized
from an ethanol/water mixture by adding H2O dropwise to
its solution in warm ethanol. Other above-mentioned chemicals were
used without further purification.
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