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-(2-(2-(2-Methoxyethoxy)ethoxy)ethyl)23-
tion occurred, the product was collected by decanting upper
liquid, followed by washing with water several times and
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benzylimidazolium TFSI (IL-3)
ꢀ
Compound IL-3 (8.24 g, 81% yield) was prepared from 2c
according to the general procedure for IL-1. A viscous
golden-brown liquid was obtained (7.18 g, 67% yield).
then drying under high vacuum (ꢂ10 mTorr) at 70 C for at
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least 48 h to remove residual solvent (9.63 g, 63% yield).
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H NMR (500 MHz, d -DMSO): d 5 3.31 (s, 3H), 3.68 (t, 2H),
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H NMR (500 MHz, d -DMSO): d 5 3.29 (s, 3H), 3.49 (m, 2H),
4.36 (t, 2H), 5.31 (d, 1H), 5.42 (s, 2H), 5.88 (d, 2H), 6.74 (q,
1H), 7.38 (d, 2H), 7.52 (d, 2H), 7.75 (s, 1H), 7.79 (s, 1H),
9.24 (s, 1H).
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3.56 (m, 4H), 3.61 (m, 2H), 3.81 (t, 2H), 4.33 (t, 2H), 5.30 (s,
2H), 7.13 (s, 1H), 7.33 (m, 2H), 7.38 (m, 3H), 7.49 (m, 1H),
8.88 (s, 1H).
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-(2-(2-Methoxyethoxy)ethyl)23-
2
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1-Methyl-PEO(350)23-benzylimidazolium TFSI (IL-8)
(4-vinylbenzyl)imidazolium TFSI (5b)
Compound IL-8 was prepared from 2d (8.92 g, 77% yield)
according to the general procedure for IL-1. A viscous yellow
liquid was obtained (7.54 g, 69% yield).
Compound 5b was prepared from 3b according to the gen-
eral procedure for 5a. A viscous golden-brown liquid was
obtained (8.47 g, 57% yield).
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H NMR (500 MHz, d -DMSO): d 5 3.28 (m, 3H), 3.51 (m,
H NMR (500 MHz, d -DMSO): d 5 3.18 (s, 3H), 3.39 (t, 2H),
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2H), 3.80 (s, 2H), 4.33 (s, 2H), 5.31 (m, 2H), 7.32 (m, 3H),
.37 (m, 3H), 7.51 (s, 1H), 8.93 (s, 1H).
3.52 (t, 2H), 3.76 (t, 2H), 4.36 (t, 2H), 5.31 (d, 1H), 5.42 (s,
2H), 5.88 (d, 2H), 6.74 (q, 1H), 7.38 (d, 2H), 7.52 (d, 2H),
7.75 (s, 1H), 7.80 (s, 1H), 9.21 (s, 1H).
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-Methyl-PEO(550)23-benzylimidazolium TFSI (IL-12)
Compound IL-12 was prepared from 2e (8.32 g, 73% yield)
according to the general procedure for IL-1, with the excep-
tion that work-up was facilitated by heating to 65 C to pre-
cipitate the IL from DI water. A viscous yellow liquid was
obtained (6.97 g, 61% yield).
1-(2-(2-(2-Methoxyethoxy)ethoxy)ethyl)23-
(4-vinylbenzyl)imidazolium TFSI (5c)
Compound 5c was prepared from 3c according to the gen-
eral procedure for 5a. A viscous golden-brown liquid was
obtained (9.80 g, 65% yield).
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ꢀ
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H NMR (500 MHz, d -DMSO): d 5 3.31 (m, 3H), 3.54 (m,
H NMR (500 MHz, d -DMSO): d 5 3.20 (s, 3H), 3.39 (m, 2H),
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2H), 3.80 (t, 2H), 4.35 (t, 2H), 5.33 (m, 2H), 7.27 (m, 1H),
.34 (m, 6H), 7.53 (s, 1H), 8.95 (s, 1H).
3.47 (m, 2H), 3.53 (m, 2H), 3.77 (m, 2H), 4.36 (t, 2H), 5.30
(d, 1H), 5.41 (s, 2H), 5.86 (d, 2H), 6.74 (q, 1H), 7.38 (d, 2H),
7.52 (d, 2H), 7.75 (s, 1H), 7.78 (s, 1H), 9.21 (s, 1H).
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-Methyl-PEO(750)23-benzylimidazolium TFSI (IL-17)
Compound IL-17 was prepared from 2f (9.23 g, 81% yield)
according to the general procedure for IL-1, with the excep-
tion that it was facilitated by heating to 65 C (6.03 g, 53%
1-Methyl-PEO(350)23-(4-vinylbenzyl)imidazolium
TFSI (5d)
Compound 5d was prepared from 3d according to the gen-
eral procedure for 5a. A viscous yellow liquid was obtained
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ꢀ
yield). A pale-yellow liquid was obtained.
(
10.52 g, 61% yield).
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H NMR (500 MHz, d -DMSO): d 5 3.34 (m, 3H), 3.56 (m,
3H), 3.83 (t, 2H), 4.37 (t, 2H), 5.35 (m, 2H), 7.32 (m, 1H),
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H NMR (500 MHz, d -DMSO): d 5 3.23 (s, 3H), 3.42 (m, 2H),
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.33 (m, 6H), 7.56 (s, 1H), 9.01 (s, 1H).
3.49 (m, 24H), 3.54 (m, 2H), 3.77 (t, 2H), 4.35 (t, 2H), 5.31
d, 1H), 5.42 (s, 2H), 5.86 (d, 2H), 6.74 (q, 1H), 7.38 (d, 2H),
.52 (d, 2H), 7.76 (s, 1H), 7.79 (s, 1H), 9.20 (s, 1H).
(
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Synthesis of PILs
General procedure for the Synthesis of
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-Methyl-PEO-3-(4-vinylbenzyl)imidazolium TFSI
-(2-Methoxyethyl)23-(4-vinylbenzyl)imidazolium
1-Methyl-PEO(550)23-(4-vinylbenzyl)imidazolium
2
TFSI (5e)
2
Cl (5a)
Compound 5e was prepared from 3e according to the gen-
eral procedure for 5a, with the exception that work-up was
facilitated by heating to 65 C to precipitate the product
from DI water. A viscous yellow liquid was obtained
(10.72 g, 58% yield).
A small amount of hydroquinone (2–4 mg) was added to the
reaction mixture to inhibit self-polymerization. 4-Vinylbenzyl
chloride (4.58 g, 3 mmol) was added dropwise to a solution
of 2a (3.78 g, 3 mmol) in toluene (25 mL) at room tempera-
ꢀ
ꢀ
ture, and the mixture was stirred for 24 h at 65 C. A two-
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H NMR (500 MHz, d
.47 (m, 44H), 3.54 (m, 2H), 3.78 (t, 2H), 4.34 (t, 2H), 5.29
d, 1H), 5.40 (s, 2H), 5.85 (d, 2H), 6.73 (q, 1H), 7.37 (d, 2H),
.51 (d, 2H), 7.75 (s, 1H), 7.77 (s, 1H), 9.19 (s, 1H).
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-DMSO): d 5 3.22 (s, 3H), 3.41 (m, 2H),
phase system was formed, and the toluene was removed
from the flask by pipette. The remaining liquid was washed
three times with diethyl ether and then placed under vac-
uum to remove any remaining solvent. A viscous golden-
brown liquid 4a resulted, and the chloride was subsequently
3
(
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2
exchanged with TFSI in the following reaction. A solution
1-Methyl-PEO(750)23-(4-vinylbenzyl)imidazolium
2
containing 4a (20 mmol) and 1.1 equiv amount of LiTFSI
TFSI (5f)
(
6.31 g, 22 mmol) was prepared in DI water (5 mL) and was
Compound 5f was prepared from 3f according to the general
procedure for 5a, with the exception that it was facilitated
stirred overnight at room temperature. After phase separa-
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