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5 protocols using 6 bromohexanoyl chloride

1

Brominated PPO Membrane Synthesis

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Poly(2,6-dimethyl-1,4-phenylene oxide) (PPO) was purchased from Asahi Kasei Corp (Tokyo, Japan). 6-bromohexanoyl chloride, aluminum chloride, 1,2-dichloroethane anhydrous, trimethyl ammonium solution (45 wt% in DI water) and N,N,N’N’-tetramethyl-1,6-hexanediamine (TMHDA) were obtained from Sigma Aldrich Korea (Yongin, Korea). Methyl alcohol (MeOH), N-methyl-2-pyrrolidone (NMP) and potassium hydroxide (KOH) were purchased from Daejung Chemical (Siheung, Korea). The polyethylene (PE) support was provided from W-SCOPE KOREA (Ochang, Korea).
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2

Synthesis of Tailored PPO/SEBS Membranes

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Asahi Kasei Co. (Tokyo, Japan) provided the poly (2,6-dimethyl-1,4-phenylene oxide) (PPO) (Mn = 34 000 g mol−1, Mw = 59,000 g mol−1). Kraton (Houston, TX, USA) was requested to provide Poly(styrene-b-ethylene-co-butylene-b-styrene) (SEBS, A1533H) with a 57% styrene content. Trimethylamine solution (~45 wt% in H2O), copper(I) bromide (CuBr(I), 98%), chlorobenzene (99.5%), 6-bromohexanoyl chloride (97%), aluminum chloride (AlCl3), and 3-dimethylamino-1-propyne (97%) were all purchased from Sigma–Aldrich (St. Louis, MO, USA). The following substances were bought from TCI (Tokyo, Japan): N-bromosuccinimide (NBS, 98%), sodium azide (NaN3, 99%), N,N,N′,N″,N″-pentamethyldiethylenetriamine (PMDTA, 99%), and dimethylamine (approx. 10% in THF). Alfa-Aesar (Haverhill, MA, USA) provided triethyl silane (98%) for purchase. Alternative commercial providers were used to obtain other chemicals that were not mentioned above. Throughout the investigation, deionized (DI) water was used for membrane treatment and property evaluations.
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3

Synthesis and Characterization of Functionalized Compounds

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Methanesulfonic acid (MSA, 99%), 6-bromohexanoyl chloride (97%), sodium azide (99.5%), dibenzocyclooctyne-amine (DBCO-NH 2 ), N ε -carbobenzoxy-L-lysine (CbzLys, 99%), triphosgene (98%), trifluoroacetic acid (99%), hydrobromic acid (33 wt% in acetic acid), citraconic anhydride (CA, 98%), 3-(4,5dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT, 98%), 3,3′-dipropylthiadicarbocyanine iodide (DiSC 3 (5), 98%), N-phenyl-1-naphthylamine (NPN, 98%), fluorescamine (98%), calcein, and Triton X-100 were purchased from Sigma-Aldrich Corp. (St Louis, MO).
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4

Synthesis of Benzene-Sulfonyl Compounds

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Benzenesulfonyl chloride (99%), styrene (99%), 2,2′-azobis(2-methylpropionitrile) (AIBN; 0.2 M in toluene), activated basic alumina, AlCl3 (99%), 6-bromohexanoyl chloride (97%), 3-bromopropionyl chloride (technical grade), trifluoroacetic acid (97%), triethylsilane (98%), 45 wt% trimethylamine in H2O, anhydrous toluene, 1,2-dichloroethane, N,N-dimethylformamide (DMF), and N-methyl-2-pyrrolidone (NMP for HPLC) were obtained from Aldrich and used without further purification. KOH was obtained from Daejung Chemicals Co.
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5

Synthesis and Characterization of Novel Compounds

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Lithocholic acid (95%, Aldrich), lithium aluminum hydride (95%, Aldrich), 2-bromoacetyl chloride (95%, Aldrich) and 6-bromohexanoyl chloride (97%, Aldrich) were used as received. N,N,N′,N′-tetramethyl-1,2-ethanediamine (99%, TCI) and N,N,N′,N′-tetramethyl-1,6-hexanediamine (99%, Aldrich) were distilled before use. Tetrahydrofuran (THF) and N, N-dimethylformamide (DMF) were dried over drying columns. Ampicillin was purchased from VWR as the pure form. All other reagents and solvents were from commercial resources and used as received unless otherwise mentioned. Spectrum Spectra/Por® 3 Dialysis Membranes with MWCO 3500 were purchased from VWR. All other reagents used for biological assays were purchased from Thermo Fisher Scientific or Sigma Aldrich and will be mentioned in the respective sections.
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