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4 protocols using trifluoromethanesulfonic acid

1

Synthesis of 2-Hexyl and 3-Hexyl Acrylates

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Example 2

A mixture of 8.00 g (95 mmole) trans 3-hexene (GFS Chemicals, Powell, Ohio), 10.30 g (143 mmol) acrylic acid, and 0.50 g (3.3 mmol) trifluoromethanesulfonic acid (Alfa Aesar) was heated to 60° C. for 24 hours. The mixture was cooled to room temperature. Ethyl acetate (50 mL) was added and the mixture was washed with saturated sodium bicarbonate until the aqueous layer was basic. The organic layer was isolated and dried over MgSO4, then filtered. The solvent was removed under vacuum, then the crude oil was then distilled under reduced pressure. A colorless oil fraction was collected (4.80 g) at 43-44° C. at 8 millimeters of mercury (mmHg). The product is 32 mol % 2-hexyl acrylate and 68 mol % 3-hexyl acrylate (as determined by NMR test method).

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2

Synthesis and Characterization of Conductive Polymer Electrolyte

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Poly(diallyldimethylammonium chloride) (PolyDADMAC) (Mw = 400,000–500,000 g mol−1) 20 wt% in water, p-toluenesulfonic acid monohydrate (Tosylic acid) (98.5%) and lithium(I) bis(trifluoromethanesulfonyl)imide (LiTFSI) (99.9%) were purchased from Sigma-Aldrich. Potassium bis(fluorosulfonyl)imide (KFSI) (98%) and N-ethyl-N-methylpyrrolidinium bromide (C2mpyrBr) (99%) were supplied by abcr GmbH. Trifluoromethanesulfonic acid (TFMSA) (98%) was supplied by Alfa Aesar. 3,4-ethylenedioxythiophene (EDOT) (99%) and Amberlite™ IRN-78 ion-exchange resin, OH-form were purchased from Fisher Scientific. 1-ethyl-1-methylpyrrolidinium bis(trifluoromethylsulfonyl)imide, 99% was supplied by IoLiTec. Dialysis tubing of regenerated cellulose, pre-treated, 38 mm MWCO 1 kD (1000 Daltons) and hydrochloric acid (HCl) (37%) were purchased from Scharlab.
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3

Synthesis of Carbazole Derivatives

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Reagents and solvents were obtained from commercial sources and used as received. Carbazole (95%), acetic anhydride (99%), copper (II) nitrate trihydrate (98%), and acetic acid (99.8%) were obtained from Sigma-Aldrich. Dimethoxymethane (95%) and palladium on activated carbon, 10% Pd/C, were purchased from Acros. 1-Fluoro-4-nitrobenzene (99%), potassium carbonate (99%), potassium hydroxide (KOH, 90%), trifluoromethanesulfonic acid (F3CSO3H, 98%), and hydrazine hydrate (98%) were ordered from Alfa Aesar. Methanol (99.8%), acetone (99.5%), ethylacetate (EA, 99.8%), petroleum ether (≥90%), tetrahydrofuran (THF, 99.9%), ethanol (99.8%), and dichloromethane (DCM, 99.8%) were obtained from Showa (Tokyo, Japan).
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4

Preparation and Purification of Reagents

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THF and Et2O were dried over sodium/benzophenone and distilled prior to use. Dichloromethane, chloroform and pentane were dried over CaH2 and distilled prior to use. Acetonitrile solvent was dried using a MBraun Solvent Purification System (model MB-SPS 800) equipped with alumina drying columns. Benzaldehyde (Alfa Aesar, 98%) was dried over CaH2, distilled and stored under argon. n-Butyllithium solution 11 M in hexanes, Lithium bis(trimethylsilyl)amide, Phosphazene (P4-tBu) 0.8 M in hexane and terephthalaldehyde were purchased from Sigma-Aldrich and used without further purification. Diisopropylformamide (Alfa Aesar) and piperidinoformamide (Sigma Aldrich) were stored under argon over activated molecular sieves 4 Å. Trifluoromethanesulfonic acid (TCI), Trifluoromethanesulfonic anhydride (ABCR), and Benzaldehyde (Alfa Aesar) were distilled prior to use. Phenyllithium 1.9 M in di-n-butyl ether was purchased from Alfa Aesar and used without purification.
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