Heat transfer ionic liquids
Russ. Chem. Bull., Int. Ed., Vol. 70, No. 2, February, 2021
307
(s, 4 Н, СН2—N); 7.41 (m, 2 Н, =СН); 7.62 (m, 2 Н, =СН).
13C NMR (DMSO-d6, 75.47 MHz), δ: 0.48, 9.74, 35.26, 40.21,
113.45, 117.80, 121.83, 122.07, 122.81, 126.37, 143.97. Found (%):
C, 26.23; H, 3.63; N, 9.16; F, 24.94; S, 13.91; Si, 6.26.
C20H32N6O9F12S4Si2, molecular mass of 912.92. Calculated (%):
С, 26.31; H, 3.53; N, 9.21; F, 24.97; S, 14.05; Si, 6.15.
1,3-Bis[(1,2-dimethylimidazolium-3-yl)methyl]-1,1,3,3-tetra-
ethyldisiloxane bis(trifluoromethylsulfonyl)amide (4b). The yield
was 90%. 1H NMR (DMSO-d6, 300.13 MHz), δ: 0.63 (m, 8 Н,
СН2СН3); 0.86 (m, 12 Н, СН2СН3); 2.53 (s, 6 Н, С—СН3);
3.74 (s, 6 Н, N—СН3); 3.87 (m, 4 Н, N—СН2); 7.38 (m, 2 Н,
=СН); 7.62 (m, 2 Н, =СН). 13C NMR (DMSO-d6, 75.47 MHz),
δ: 5.54, 6.25, 9.68, 35.25, 37.80, 113.60, 117.80, 121.90, 121.96,
122.94, 126.40, 144.04. Found (%): C, 29.71; H, 4.22; N, 8.63;
F, 23.51; S, 13.27; Si, 5.85. C24H40N6O9F12S4Si2, molecular
mass of 969.03. Calculated (%): C, 29.75; H, 4.16; N, 8.67;
F, 23.53; S, 13.23; Si, 5.80.
88%. 1H NMR (DMSO-d6, 300.13 MHz), δ: 0.16 (s, 12 Н,
СН3—Si); 3.87 (s, 6 Н, СН3—N); 3.89 (s, 4 Н, СН2—N); 7.52
(m, 2 Н, =СН); 7.69 (m, 2 Н, =СН); 8.90 (s, 2 Н, NCHN).
13C NMR (DMSO-d6, 75.47 MHz), δ: 0.96, 36.16, 41.37, 113.42,
117.81, 122.07, 123.54, 124.15, 126.31, 136.25. Found (%): C, 24.33;
H, 3.35; N, 9.46; F, 25.73; S, 13.51; Si, 6.45. C18H28N6O9F12S4Si2,
molecular mass of 884.87. Calculated (%): С, 24.43; H, 3.20; N,
9.50; F, 25.76; S, 14.49; Si, 6.35.
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1,3-Bis[(1,2-dimethylimidazolium-3-yl)propyl]-1,1,3,3-tetra-
methyldisiloxane bis(trifluoromethylsulfonyl)amide (4c). The yield
was 95%. 1H NMR (DMSO-d6, 300.13 MHz), δ: 0.04 (s, 12 Н,
СН3—Si); 0.49 (m, 4 Н, CH2CH2CH2Si); 1.67 (m, 4 Н,
CH2CH2CH2Si); 2.55 (s, 6 Н, СН3—С); 3.74 (s, 6 Н, СН3—N);
4.06 (m, 4 Н, NCH2CH2CH2Si); 7.61 (m, 4 Н, =СН). 13C NMR
(DMSO-d6, 75.47 MHz), δ: 0.33, 9.43, 13.50, 23.90, 34.97,
50.51, 113.52, 117.79, 121.16, 122.05, 122.70, 126.32, 144.54.
Found (%): C, 29.66; H, 4.27; N, 8.60; F, 23.50; S, 13.19;
Si, 5.87. C24H40F12N6O9S4Si2, molecular mass of 969.03. Calcul-
ated (%): C, 29.75; H, 4.16; N, 8.67; F, 23.53; S, 13.23; Si, 5.80.
1,3-Bis[(1-ethyl-2-isopropylimidazolium-3-yl)methyl]-
1,1,3,3-tetramethyldisiloxane bis(trifluoromethylsulfonyl)amide
1
(4d). The yield was 95%. H NMR (DMSO-d6, 300.13 MHz),
δ: 0.20 (s, 12 Н, СН3—Si); 1.39 (m, 18 Н, СН3—СН2 + СН3—
СН—СН3); 3.62 (m, 2 Н, СН3—СН—СН3); 3.89 (s, 4 Н,
NCH2Si); 4.26 (m, 4 Н, СН3СН2—N); 7.44 (m, 2 Н, =СН);
7.74 (m, 2 Н, =СН). 13C NMR (DMSO-d6, 75.47 MHz), δ:
0.33, 15.99, 19.18, 24.25, 40.56, 43.86, 113.55, 117.82, 122.08,
123.04, 126.34, 148.47. Found (%): C, 31.27; H, 4.52; N, 8.36;
F, 22.85; S, 12.82; Si, 5.59. С26Н44N6O9F12S4Si2, molecular
mass of 997.08. Calculated (%): C, 31.32; H, 4.45; N, 8.43;
F, 22.87; S, 12.86; Si, 5.63.
1,3-Bis[(1-(2-methoxyethyl)-2-methylimidazolium-3-yl)-
methyl]-1,1,3,3-tetramethyldisiloxane bis(trifluoromethylsulf-
onyl)amide (4e). The yield was 95%. 1H NMR (DMSO-d6,
300.13 MHz), δ: 0.14 (s, 12 Н, СН3—Si); 2.56 (s, 6 Н, СН3—С);
3.24 (s, 6 Н, СН3—N); 3.65 (m, 4 Н, СН2—О); 3.84 (m, 4 Н,
NCH2Si); 4.32 (m, 4 Н, СН2—N); 7.44 (m, 2 Н, =СН); 7.65
(m, 2 Н, =СН). 13C NMR (DMSO-d6, 75.47 MHz), δ: 0.80,
9.89, 40.23, 48.09, 58.53, 70.39, 113.55, 117.81, 122.06, 122.12,
126.34, 144.04. Found (%): C, 28.69; H, 4.10; N, 8.32; F, 22.76;
S, 12.77; Si, 5.66. C24H40F12N6O11S4Si2, molecular mass of
1001.03. Calculated (%): C, 28.80; H, 4.03; N, 8.39; F, 22.78;
S, 12.81; Si, 5.61.
α,ω-Bis{[(1,2-dimethylimidazolium-3-yl)methyl(dimethyl)-
silyl}polydimethylsiloxane bis(trifluoromethylsulfonyl)amide (5).
The yield was 85%. 1H NMR (DMSO-d6, 300.13 MHz), δ: 0.05
(m, СН3—Si); 0.19 (m, СН3—Si); 2.54 (s, С—СН3); 3.76
(s, N—СН3); 3.83 (m, N—СН2Si); 7.42 (m, =СН); 7.62 (m, =СН).
13C NMR (DMSO-d6, 75.47 MHz), δ: –1.11, 0.79, 9.35, 34.54,
40.39, 113.56, 117.82, 121.66, 122.07, 122.50, 126.33, 143.83.
1,1,3,3-Tetramethyl-1,3-bis[(1-methylimidazolium-3-yl)meth-
yl]disiloxane bis(trifluoromethylsulfonyl)amide (4f). The yield was
20. H. Liu, E. Maginn, A. E. Visser, N. J. Bridges, E. B. Fox,
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