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3 protocols using triethylene glycol monomethyl ether

1

Synthesis of Well-Defined Polymers

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Acetone, ascorbic acid, azobisisobutyronitrile (AIBN), 2,2'-bipyridine, α-bromoisobutyryl bromide, copper(II) chloride (CuCl2), ethylene glycol, 1,4-dioxane, methacryloyl chloride, potassium ethyl xanthogenate, potassium persulphate, tetrahydrofuran (THF), triethylamine, triethylene glycol monomethyl ether, tris(pyridin-2-ylmethyl)amine (TPMA), 1,3,5-trioxane, N-vinylpyrrolidone (NVP) were purchased from Sigma Aldrich (UK) and were used without further purification. Dichloromethane (DCM) was purchased from AGTC Bioproducts (UK). Ethyl acetate and hexane were purchased from VWR Chemicals (UK). Copper(I) chloride (CuCl) was purchased from Sigma Aldrich (UK) and purified prior to use by stirring the powder in glacial acetic acid for 2 h. The white solids were filtered, washed thoroughly with cold ethanol, dried in vacuo, and stored under nitrogen.
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2

Synthesis of PEGylated Alkene Monomer

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All chemicals N,N′-Dicyclohexylcarbodiimide (DCC), 2-ethoxyethanol (1EG), triethylene glycol monomethyl ether (3EG), poly(ethylene glycol) monomethyl ether (12EG, M = 550 g/mol), 2-methyl-4-pentenoic acid (MPA), and 4-(dimethylamino)pyridine (DMAP), dichloromethane (DCM), tetrahydrofuran (THF), were purchased from Sigma-Aldrich and used as received unless stated otherwise. Sodium bicarbonate solution and sodium phosphate buffer solution (PBS, 1×) were prepared in house.
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3

Synthesis and Characterization of ILs

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Materials TMOP and TEOP have been synthesized using phosphorus(V) oxychloride (99% purity, Sigma Aldrich) and respective alcohol triethylene glycol monomethyl ether (95% purity, Sigma Aldrich) and di(ethylene glycol) ethyl ether (99% purity, Sigma Aldrich). 1-Methylpyrrolidine (98% purity, Sigma Aldrich) 1,2dimethylimidazole (99% purity, Sigma Aldrich), 1-methylimidazole (98% purity, Sigma Aldrich), sodium sulfate (99% purity, Sigma Aldrich), ethyl acetate (99.5% purity, Sigma Aldrich) and hexane (99% purity, Sigma Aldrich) were used without further purification. All the synthesized ILs were kept in a vacuum oven at 90 1C for at least 3 days until the water content was less than 100 ppm (Table S4, ESI †), as determined by the Karl-Fischer titration using a 917 coulometer (Metrohm) placed inside a glovebox with water and oxygen contents less than 1 ppm. Multi-walled carbon nanotubes (Sigma Aldrich, 95% carbon, O.D.  L 6-9 nm  5 mm), activated charcoal (Sigma Aldrich, 100 mesh size), polyvinyl alcohol (Merck, M W 72 000) and glass microfiber filters (Whatman s ) were used as received.
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