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8 protocols using tetrahydrofuran

1

Polymer Composite Synthesis and Characterization

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2-Acrylamido-2-methyl-1-propanesulfonic acid (AMPS), poly(1,4-phenylene ether-ether-sulfone) (PEES), TiCl3·AA and AlEt2Cl ([25 (link)] wt% in toluene) were purchased from Sigma-Aldrich (St. Louis, MO, USA). Methanol, acetone, N,N-dimethylacetamide (DMAc), N,N-dimethylformamide (DMF), tetrahydrofuran (THF), N-methylpyrrolidone (NMP), dimethyl sulfoxide (DMSO), sulfuric acid (H2SO4), were purchased from Daejung Reagents & Chemicals (Korea).
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2

Lignin Isolation from Pine Biomass

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Lignocellulose (Pinus densiflora S. et Z.) with a lignin content of 31.4% was used as the raw material for lignin isolation. ChCl, LA, pyridine, dimethylformamide (DMF), tetrahydrofuran (THF), and 1M hydrochloric acid solution were purchased from Daejung Chemical & Metals (Siheung, Korea). Palmitoyl chloride (PC) was purchased from Tokyo Chemical Industry (Tokyo, Japan). PLA (IngeoTM Biopolymers 6400D) was obtained from NatureWorks LLC (Minnetonka, MN, USA).
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3

Synthesis of Conducting Polymer Composites

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All the materials viz. aqueous solution of 99% pure pyrrole (Daejung, Seoul, Korea), anhydrous ferric chloride (Sigma Aldrich, Taufkirchen, Germany), ammonium molybdate (Merck, Darmstadt, Germany), methanol (Daejung, Seoul, Korea), acetone (Daejung, Seoul, Korea), chloroform (Daejung, Seoul, Korea), nitric acid (70%, Daejung, Seoul, Korea), and tetrahydrofuran (Daejung, Seoul, Korea) were obtained from commercial sources. Poly(styrene-isoprene-styrene) was obtained (Sigma Aldrich, Taufkirchen, Germany), containing 22% tyrene by weight. All chemicals were of reagent grade and used without further purification.
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4

Atom Transfer Radical Polymerization Synthesis

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Sodium sulfonated styrene (Na-SS ≥ 90%), copper (I) bromide (CuBr, 98%), copper (II) bromide (CuBr2, 99.999%), N,N,N′,N′′,N′′-pentamethyldiethylenetriamine (PMDETA, 99%) and diethyl ether (≥99%) were purchased from Sigma-Aldrich and used as received without any further purification unless explicitly stated. Toluene (99%), tetrahydrofuran (99%), dimethylformamide (DMF, 99.5%), and glacial acetic acid (99.7%) were purchased from Daejung Chemicals and Metals. Copper(I) bromide was purified by washing with glacial acetic acid and diethyl ether, and then filtered, dried, and stored under vacuum for further use. Atom transfer radical polymerization (ATRP) initiator 1-(chlorodimethylsilyl)propyl-2-bromoisobutyrate was synthesized by direct reaction of chlorodimethylsilane (98%) and allyl 2-bromo-2-methylpropionate (98%) in presence of Pt catalyst at room temperature as described in the Section 3.2.
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5

Synthesis of Silver-Alkylthiolate Coordination Polymer

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Alkylthiolate–silver coordination polymer was prepared referring to the previous literatures [19 (link)]. Silver nitrate (AgNO3, 4.9 × 10−3 mol; Sigma-Aldrich, Inc., St. Louis, MO, USA) was dissolved in a mixed solvent (50 mL of tetrahydrofuran (THF; Daejung Chemicals & Metals CO., LTD., Siheung, South Korea) and 25 mL of ethanol (EtOH; Daejung Chemicals & Metals CO., LTD., Tokyo South Korea)), and octadecanethiol (9.1 × 10−3 mol; Sigma-Aldrich, Inc., St. Louis, MO, USA) was dissolved in 50 mL of THF solvent. Both solutions were mixed and vigorously stirred under ambient condition. After 24 h, the obtained precipitate was separated by centrifugation and unreacted octadecanethiol moiety was washed out utilizing THF and EtOH. Thus obtained product, AgS(CH2)17CH3 coordination polymer (AgSC18) was dried in vacuum oven.
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6

Biofunctionalized Polymeric Stent Coatings

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Poly(L-lactic acid) (PLLA, Mw = 200 kDa) and poly(D,L-lactic acid) (PDLLA, R205S, Mw = 10–18 kDa) were purchased from Evonik Industries AG (Essen, Germany). The 2,3,5-triiodobenzoic acid (TIBA, 98%), magnesium hydroxide (MH, 99.0%), dopamine hydrochloride, cystamine dihydrochloride (96%), L-glutathione reduced (98.0%), tris(hydroxymethyl)aminomethane(ACS reagent, 99.8%), hexamethyldisilazane (HMDS, 99%), S-nitroso-N-acetyl-D,L-penicillamine (97%) and glutaraldehyde (GA) solution (25%) were purchased from Sigma-Aldrich (St. Louis, MO, USA). The tetrahydrofuran (THF, 99.8%), 1,4-dioxane (DO, 99.5%), and 1N-sodium hydroxide standard solution were purchased from Daejung Co. Ltd. (Seoul, Korea). The ethanol, methanol, acetonitrile, water (HPLC grade) was purchased from J.T. Baker (Phillipsburg, NJ, USA) and phosphate-buffered saline (PBS) solution was purchased from Hyclone in GE Healthcare Life Sciences (Seoul, Korea). A cell counting kit (CCK-8) was purchased from Dongin LS (Seoul, Korea). Human coronary artery endothelial cells (HCAECs), human coronary artery smooth muscle cells (HCASMCs), endothelial cell growth medium-2 (EGM-2), and smooth muscle cell growth medium (SmGM) were purchased from Lonza (Basel, Switzerland). IL-6 and IL-8 enzyme-linked immunosorbent assay (ELISA) kits were purchased from R&D Systems (Minneapolis, MN, USA).
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7

Synthesis of VP-APS Copolymer

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Vinyl pyrrolidone (VP) and mineral oil were purchased from Sigma-Aldrich Chemical Co. (St. Louis, MO, USA). Allyl phenyl sulfide (APS) was purchased from Tokyo Chemical Industry Co. Ltd., (Tokyo, Japan). 2,2’-Azobisisobutyronitrile (AIBN) was purchased from Junsei Chemical Co. (Tokyo, Japan). Tetrahydrofuran, hexane and H2O2 solution (30%) were purchased from Dae Jung Chemicals & Metals Co., Ltd. (Siheung, South Korea).
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8

Synthesis and Characterization of 6FDA-DB18C6 Membranes

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4,4′-(hexafluoroisopropylidene) di-phthalic anhydride (6FDA) and dibenzo-18-crown-6 (DB18C6) were purchased from TCI Co. Ltd. (Seoul, Korea). and were used as obtained. Bis(3-aminopropyl) terminated PDMS (Mn = 2500), triethylamine, hydrazine monohydrate, acetic anhydride, nitric acid, and anhydrous acetic acid were obtained from Sigma-Aldrich Korea (Yongin, Korea) and were used without purification. Pd/C catalyst (palladium, 10% on carbon, Type 487, dry) was purchased from Alfa-Aesar (Seoul, Korea). Ethanol, isopropanol, tetrahydrofuran, dimethylacetamide, dimethylsulfoxide, and dimethylformamide were purchased from DaeJung Chemicals & Metals Co. Ltd. (Shiheung, Korea). Trans-diamino-DB18C6 (3) was synthesized following previous reports [21 (link),22 (link)], and the procedures are described in the Supporting Information. All other chemicals were obtained from commercial sources.
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