Synthesis of IL monomer
This protocol is extracted from research article:
Ionic liquid–based click-ionogels
Sci Adv, Aug 23, 2019; DOI: 10.1126/sciadv.aax0648

A mixture containing 1-vinyl imidazole (10.34 g, 0.11 mol) and 1-bromobutane (13.7 g, 0.10 mol) was stirred at room temperature for 3 days. The synthesized 1-butyl-3-vinyl imidazolium bromide (BVIm-Br) was washed with diethyl ether three times and then dried under vacuum at 25°C for 12 hours to give a colorless transparent liquid (16.78 g, yield: 72.6%).

A solution of BVIm-Br (3.47 g, 1.50 mmol) in water was added to NH4BF4 (1.78 g, 1.70 mmol) solution and stirred for 5 hours at room temperature. Then, the solution was extracted with dichloromethane three times. The combined organic phase was washed with water and then dried by MgSO4 and spin evaporation to give the yellowish transparent liquid 1-butyl-3-vinyl imidazolium fluoborate (BVIm-BF4) (0.32 g, yield: 32.4%). 1H NMR (400 MHz, DMSO-d6) (ppm): 9.5 (s, 1H, N─CH═N), 8.2 (s, 1H, CH─CH═N), 7.8 (s, 1H, CH─CH═N), 7.2 (m, 1H, N─CH═CH2), 5.9 (d, 1H, N─CH═CH), 5.3 (d, 1H, N─CH═CH), 4.2 (m, 2H, N─CH2─CH2), 1.7 (m, 2H, CH2─CH2─CH2), 1.3 (m, 2H, CH2─CH2─CH2), 0.7 (m, 3H, CH2─CH3) (fig. S2).

The similar procedure was used for synthesizing 1-propyl-3-methyl-imidazolium fluoborate (IL-BF4). 1H NMR (400 MHz, DMSO-d6) (ppm): 9.2 (s, 1H, CH─CH═N), 7.8 (d, 1H, CH─CH═N), 4.2 (m, 2H, N─CH2─CH2), 3.7 (s, 3H, N─CH3), 1.8 (m, 2H, CH2─CH2─CH3), 0.8 (m, 3H, CH2─CH3) (fig. S3).

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