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5 protocols using 1 bromoethane

1

Synthesis of Polymer Precursors

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Ethylene glycol (EG, 99%), pyridine (99%), 2-bromopropanoyl bromide (98%), potassium ethyl xanthate (97%), 1-bromoethane (98%), azobisisobutyronitrile (AIBN, 99%), 2.0 M lithium diisopropylamide (LDA) in tetrahydrofuran (THF), diphenyl phosphate (DPP, 97%), and anhydrous magnesium sulfate (MgSO4, 99%) were purchased from Sigma-Aldrich (St. Louis, MO, USA) and were used without purification. The solvents N-vinylpyrrolidone (NVP, 99%) and ε-caprolactone (CL, 99%) were distilled and stored in a molecular sieve prior to use.
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2

Synthesis and Characterization of Ionic Liquids

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For the synthesis of the ILs, choline hydroxide in methanol [Cho][OH]/MeOH 45%, methanol, Amberlite® IRA-400 chloride form, 1-bromoethane, and glycine from Sigma–Aldrich (Saint Louis, MO, USA) were used as well as 1-methylimidazole and acetonitrile from VWR (Fontenay-sous-Bois, France) and sodium hydroxide (NaOH) from PanReact AppliChem (Barcelona, Spain). Rutin was obtained from Fragron (São Paulo, Brazil).
Regarding the cell viability studies, trypsin, penicillin–streptomycin solution, fetal bovine serum, dimethyl sulfoxide (DMSO), and thiazolyl blue tetrazolium bromide (MTT) were acquired from Sigma–Aldrich (Saint Louis, MO, USA) and Dulbecco’s modified Eagle’s medium (DMEM) was purchased by Biowest (Nuaillé, France).
For the preparation of transfersomes, methanol was from Carlo Erba Reagenti SpA (Rodano, Italy), chloroform from Sigma–Aldrich Chemie Gmbh (Munich, Germany), Tween® 80 from Sigma–Aldrich (Saint Louis, MO, USA), and soy phosphatidylcholine from Alfa Aesar (Kandel, Germany). For the release study, phosphate-buffered saline (PBS, pH 7.4) was prepared as previously described [54 (link)].
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3

Synthesis and Characterization of Imidazolium Compounds

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1-Vinylimidazole
(99%) was purchased from Alfa Aesar (Kandel, Germany)
and distilled under reduced pressure at 80 °C prior to use. Tributylphosphine
(97%), diallyldimethylammonium chloride (65% solution in water), 1-bromoethane,
1-chlorobutane, and 1-methylimidazole were purchased from Sigma-Aldrich
(Steinheim, Germany). 1-methylimidazole was distilled over KOH before
use. Sodium salicylate (99%) and lanthanum(III)-chloride heptahydrate
were purchased from ABCR (Kalrsruhe, Germany) and used as received.
Terbium (III,IV) oxide (99.99%) was purchased from SmartElements (Vienna,
Austria). Choline chloride (97%) and ethanol (99.5%) were purchased
from Acros Organics (Geel, Belgium).
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4

Synthesis of Functionalized Polymers

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Carbonyl
biscaprolactam (CBC, >99%) was obtained from Actu-all
(Oss, The Netherlands). Bis(hexamethylene) triamine (BHTA, high purity), N,N-dimethylethenediamine
(DMEN, ≥98.0%), N,N-dimethylethylenediamine,
1-bromoethane, 1-bromobutane, 1-bromohexane, 1-bromooctane, and 1-bromododecene
(99%) were purchased from Sigma-Aldrich. Poly(vinyl alcohol) (PVA,
88% hydrolyzed, average Mn = 22.000 Da)
was purchased from Acros Organics. Benzoyl peroxide (Luperox A75,
75%, remainder water) was purchased from Sigma-Aldrich. Methyl methacrylate
(MMA, 100 ppm hydroquinone as a stabilizer) was obtained from Merck.
Surfactants Tego*wet 245 and 500 were purchased from Evonik Tego Chemie.
DMF (anhydrous) and toluene (anhydrous) were obtained from Sigma-Aldrich.
All of the chemicals were used as received and without purification.
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5

Synthesis of Imidazolium-Based Ionic Liquids

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Reagents (1-methylimidazole, 1-chlorohexane, 1-bromoethane, 1-bromobutane, 1bromohexane, 1-iodohexane, copper(I) halides) were purchased from Sigma Aldrich and used without further purification. Hydrogen (99.9995% HP grade) and carbon monoxide (99.9% CP grade) were supplied by BOC. Gas mixtures containing CO:H 2 and CO:N 2 (each 50:50 (±2)) were supplied by BOC. N 2 gas for inert atmosphere work, and for use in high pressure reactions was supplied by an in-house generator. 13 CO (< 5% 18 O, 99% 13 C) was purchased from Sigma Aldrich and used directly from the cylinder. The 1-alkyl-3methylimidazolium halide [C n mim]X salts were prepared by the reaction of 1-methyl imidazole with the requisite alkyl halide according to published procedures (see ESI). [71] [72] [73] The hygroscopic salts were stored under nitrogen.
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