Allyl bromide

The following reagents were used: 1-methylimidazole (Alfa Aesar, 99%), 1-vinylimidazole (Sigma-Aldrich, 99%), allyl bromide (BHD, 99%), diethyl sulfate (Acros Organics, 99%), sodium dicyanamide (Aldrich, ≥97%). The solvents used for reaction media and/or purification processes are the following: dichloromethane (Carlo Erba Reagents, 99.9%), ethanol (LabChem), acetone (LabChem), acetonitrile (Carlo Erba Reagents, 99.8%), diethyl ether (LabChem, 99.9%). The reagent sodium trifluoromethanesulfonate, and the ILs [EMIM][TfO], [EMIM][EtSO₄], [BMIM][TfO], [BMIM][DCA], [C₂OHMIM][TfO], and [C₂OHMIM][DCA] were kindly provided by Solchemar company (Portugal). The purity of these ILs is greater than 98%, according to the supplier. The commercial lubricant PEG 200 is from FLUKA (Sigma-Aldrich), ref: 81150. The substrates used for tribological tests and contact angle measurements are silicon wafers b100N with 0.5 mm of thickness and a roughness below 0.1 nm. Stainless steel AISI 316L spheres with 3 mm of diameter were used as counter bodies.

All chemicals, if not specified otherwise, were used as received without further purification. Poly (2,6-dimethyl-1,4-phenyleneoxide) (PPO) (M_n = 20,000, Đ = 2.5) was purchased from Polysciences Inc. and dried under vacuum at 60 °C overnight before use. Methanol (99.9%), ethanol (99.9%) and chloroform (99.8%) were purchased from Fisher Scientific. N-Bromosuccinimide (NBS) (99%), 2,2′-azobis(2-methylpropionitrile) (AIBN) (98%), tetrahydrofuran (THF, ACS, >99%), diethyl ether (>99%), chloroform-d (CDCl₃-d, 99.9% D), Irgacure^® 2959, D₂O (99.9% D) and 1,2-dichloroethane (99.8%) were purchased from Sigma-Aldrich (Merck KGaA, Darmstadt, Germany). Dimethyl sulfoxide-d₆ (DMSO-d₆, 99.9%), N-methyl-2-pyrrolidone (NMP, reagent grade) were supplied from Acros Organics. Chlorobenzene (ACS reagent, ≥99.5%), diallymethylamine (97%) and piperidine (≥99%) were bought from ABCR GmbH. Allyl bromide (98%) and allyl chloride (98%) were bought from Alfa Aesar. The electrolytes MV and TMA-TEMPO were provided by JenaBatteries GmbH (Jena, Germany). FAA-3-50^® was purchased from Fumatech BWT GmbH (Bietigheim-Bissingen, Germany).

Diallyldimethylammonium chloride (65 wt % in H₂O) and triallylamine (99%) were purchased from Sigma Aldrich, and piperazine and D₂O (99.9%) were obtained from Merck KGaA (Darmstadt, Germany). Allyl bromide (99%), potassium carbonate (99%), methanol (99%), and 1,3-bis(4-piperidyl)propane (97+%) were purchased from Alfa Aesar (Kandel, Germany). The anion exchange-resin Lewatit Monoplus MP 800 was provided by Lanxess (Leverkusen, Germany). Chloroform (≥99%), acetone (≥99%), bidistilled water, potassium hydroxide, dichloromethane (≥99%), potassium persulfate, sodium metabisulphite, N,N′-methylenebisacrylamide and sodium hydroxide (97%) were obtained from VWR International GmbH (Darmstadt, Germany). All chemicals were used as received. Polyester filter bags with a maximum mesh size of 90 µm were purchased from Rosin Tech Products (Bethpage, NY, USA).

The anion exchange-resin Lewatit Monoplus MP 800 was provided by Lanxess (Leverkusen, Germany). Double-distilled water, potassium hydroxide, chloroform (≥99%), acetone (≥99%), dichloromethane (≥99%), potassium persulfate, sodium metabisulphite, sodium hydroxide (97%) and N,N’-methylenebisacrylamide were obtained from VWR International GmbH (Darmstadt, Germany). Potassium carbonate (99%), allyl bromide (99%), methanol (99%) and 1,3-bis(4-piperidyl)propane (97+%) were obtained from Alfa Aesar (Kandel, Germany), diallyldimethylammonium chloride (65 wt% in H₂O) and triallylamine (99%) were obtained from Sigma Aldrich. Piperazine, diallylamine (97%) and D₂O (99.9%) were purchased from Merck KGaA (Darmstadt, Germany). The polyester filter bags with a maximum mesh size of 90 µm were bought from Rosin Tech Products (Bethpage, NY, USA).

PPO (Mn 20,000 and Polydispersity ~2.5) was purchased from Polysciences, Inc. Chlorobenzene (ACS reagent, ≥99.5%), N-methyl-2-pyrrolidone (NMP, reagent grade), tetrahydrofuran (THF, ACS, >99%), diethyl ether (>99%), 1,2-dichloroethane (99.8%), allyl bromide (98%), allyl chloride (98%) and chloroform (99.8%) were purchased from Alfa Aesar (Thermo Fisher, Kandel, Germany). Diallymethylamine (97%) and piperidine (≥99%) were bought from ABCR GmbH (Karlsruhe, Germany). Dimethyl sulfoxide-d₆ (DMSO-d₆, 99.9%) was supplied from Acros Organics ((Thermo Fisher, Kandel, Germany). N-bromosuccinimide (NBS, 99%), 2,2′-azobis(2-methylpropionitrile) (AIBN, 98%), methanol (99.9%) and chloroform-d (CDCl₃-d, 99.9% D) were purchased from Sigma-Aldrich (Merck KGaA, Darmstadt, Germany). 2-hydroxy-4′-(2-hydroxyethoxy)-2-methylpropiophenone (Irgacure D-2959) was bought from Ciba Specialty Chemicals Inc (Basel, Switzerland). Cellophane™ 350PØØ was purchased from Futamura Chemical Co. Ltd. (Hamburg, Germany). Celgard^® membranes were kindly provided by Celgard, LLC (France). Zirfon^® and PBI^® were provided by AGFA Gevaert NV (Mortsel, Belgium) and Fumatech BWT GmbH (Bietigheim-Bissingen, Germany), respectively. All chemicals were used without further purification.

1-methylImidazole (99%), 1,4-dibomobutane (98%), 1,6-dibromohexane (97%), dicyclopentadiene (95%), hydroquinone (99%), and dimethylacetamide (DMAc, 99.5%) were purchased from BeanTown Chemical (Hudson, NH, USA). Imidazole (99%) and Grubbs’ catalyst (G2, 97%) were purchased from Sigma-Aldrich (Saint Louis, MO, USA). 1,10-dibromodecane (97%), 1,2-dimethylImidazole (98%), and allyl bromide (99%) were purchased from AlfaAesar (Tewksbury, MA, USA). Lithium bistriflimide (LiTf₂N) was purchased from 3M (Minneapolis, MN, USA). Ethyl vinyl ether (EVE, >98%) and sodium hydride (NaH, 60 wt% in mineral oil) were purchased from TCI (Portland, OR, USA). Dichloromethane (DCM), dimethylformamide (DMF) acetone, acetonitrile (ACN), diethyl ether (Et₂O), ethyl acetate (EtOAc), and hexanes were ACS Grade, and purchased from VWR (Atlanta, GA, USA). Unless otherwise noted, all the chemicals were obtained from commercial sources, and used as received.