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4 protocols using biphenyl

1

Biphenyl Synthesis and Ionic Liquid Preparation

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For the CTF-biphenyl synthesis, anhydrous aluminum chloride (AlCl3; 98.5%) was received from Arcos Organics, cyanuric chloride (99%) was obtained from Sigma-Aldrich, and biphenyl (99%) from Alfa Aesar. biphenyl was recrystallized from ethanol before usage. For the synthesis of the IL, [BMIm][NTf2] 1-chlorobutane (99%) was purchased from Merck, 1-methylimidazole (99%) and lithium bis(trifluoromethanesulfonyl)imide (Li[NTf2]; 99%) were obtained from Fluorochem, activated charcoal (extra pure) from Merck, and acidic aluminum oxide (150 m2/g; Brockmann grade 1) from Alfa Aesar. The solvents acetone (≥99.8%), dichloromethane (DCM; 99.99%), and ethyl acetate (≥99%) were received from Fisher Scientific; and methanol (MeOH; ≥99.8%) and tetrahydrofuran (THF; ≥99.9%) from Sigma-Aldrich. The polymer Matrimid® 5218 (BTDA/DAPI) was provided by Huntsman Advanced Materials. The gases CO2 (grade 4.5), CH4 (grade 4.5), and He (grade 5.0) were received from Air Liquide.
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2

Synthesis of Organic Compounds

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Analytical grade benzyl alcohol was obtained from Beijing Chemical Reagents, China. Pt(acac)2 (99%), Ni(acac)2 (99%), PVP (molecular weight (MW)=8,000), nitrobenzene, benzaldehyde, benzoic acid, styrene, 2,4,6-trimethylstyrene, trans-stilbene, biphenyl, anisole and Platinum (5% on carbon) were purchased from Alfa Aesar. 2,5-dihydroxyterephthalic acid, 4,4′-dimethyl-trans-stilbene and 1-chloro-2-nitrobenzene were acquired from TCI. Aniline was purchased from J.K Scientific. All of the chemicals used in this experiment were analytical grade and used without further purification.
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3

Heavy Metal Ion Adsorption Evaluation

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All chemicals and
reagents were used as received without further purification. Biphenyl
(99% purity), 1,3,5-trihydroxybenzene (phloroglucinol, 98%), 4,4′-methylenedianiline
(97% purity), sodium nitrite (98% purity), and sodium carbonate (98%
purity) were purchased from Alfa Aesar. Nitric acid (70%), sulfuric
acid (98%), hydrochloric acid (HCl, 37%), and toluene (high purity)
were obtained from Acros. Methanol (99.9% purity), N,N′-dimethylformamide (DMF, 99% purity) and
Pd/C (5% w/w) were purchased from Millipore Sigma. Ultrapure water
was obtained using a Milli-Q Ultrapure instrument. For the metal removal
analysis, standard solutions (1000 ppm) containing lead (Pb(II)),
mercury (Hg(II)), arsenic (As(III)), copper (Cu(II)), chromium (Cr(III)),
and nickel (Ni(II)) were purchased from Sigma-Aldrich and used to
prepare the required solutions for testing with a predetermined initial
concentration. For gas sorption analysis, nitrogen gas (99.999% purity),
carbon dioxide gas (99.99% purity), and helium (99.999% purity) were
supplied from Air Liquide, Dammam, Saudi Arabia.
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4

Synthesis of Heterocyclic Compounds

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N-methyl pyrrolidine (98%, Alfa Aesar, Haverill, MA, USA), N-methyl piperidine (99%, Alfa Aesar, Haverill, MA, USA), 1,5 dibromopentane (98%, Alfa Aesar, Haverill, MA, USA), potassium carbonate (K2CO3, 99%, Merck, Rowe, NJ, USA), biphenyl (99%, Alfa Aesar, Haverill, MA, USA), 2,2,2-trifluoroacetophenone (98%, Alfa Aesar, Haverill, MA, USA), isatin (98%, Alfa Aesar, Haverill, MA, USA), trifluoroacetic acid (TFA, 99%, Alfa Aesar, Haverill, MA, USA), trifluoromethanesulfonic acid (TFSA, 99%, Fluorochem, Derbyshire, UK), potassium hydroxide (+85% pellets, Merck, Rowe, NJ, USA), acetonitrile, (99.5%, Scharlab, Quezon City, Philippines), dimethylsulfoxide (DMSO, Scharlab, Quezon City, Philippines), N-methyl pyrrolidone (NMP, Scharlab, Quezon City, Philippines) acetone (Scharlab, Quezon City, Philippines), diethyl ether (Sigma Aldrich, St. Louis, MO, USA), methanol (Sigma Aldrich, St. Louis, MO, USA), dichloromethane (DCM, Scharlab, Quezon City, Philippines), dmso-d6 (99.80 atom% Deutero, Kastellaun, Germany) were all used as received.
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