Synthesis and Thermophysical Properties of Biocompatible Cholinium-Based
Amino Acid Ionic Liquids
Duan-Jian Tao*, Zheng Cheng, Feng-Feng Chen, Zhang-Min Li, Na Hu, Xiang-Shu
Chen*
Jiangxi Inorganic Membrane Materials Engineering Research Centre, College of
Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022,
People’s Republic of China
*
Corresponding Author: Tel.: +86-791-88120533. Fax: +86-791-88120843.
E-mail: [email protected] (D.J.T.); [email protected] (X.S.C.).
SUPPORTING INFORMATION
Five [Ch][AA] ILs had been synthesized using biodegradable materials via simple
acid-base neutralization reactions, and the preparation procedure was straightforward
effective, and environmentally benign. All the yields of such AAILs were more than
80%, though it consumed too much time for synthesis. 1H NMR (Bruker DPX-300),
FT-IR spectra (Thermo Nicolet 870), elemental analysis (Elementar Vario El III),
DSC analysis (Netzsch DSC 200F3), and thermogravimetry (PerkinElmer Diamond
TG/DTA) characterization for each [Ch][AA] ILs synthesized.
[Ch][Gly]. 1H NMR (300 MHz, D2O) δ: 2.95 (2H, s, CH2NH2), 3.09 (9H, s,
(CH3)3N), 3.39–3.41 (2H, t, CH2CH2OH), 3.93–3.95 (2H, m, CH2CH2N). Elemental
analysis (%), calculated: C 47.191, N 15.730, H 10.112, found: C 47.195, N 15.718,
−
H 10.105. IR: v = 3394, 2917, 2851, 1587, 1484, 1391, 1090, 957, 869 cm-1. (Yield
89% based on the amount of [Ch]Cl).
[Ch][L-Ala]. 1H NMR (300 MHz, D2O) δ: 1.11–1.13 (3H, d, CH3CH), 3.09 (9H,
s, (CH3)3N), 3.19–3.24 (1H, q, CHNH2), 3.39–3.42 (2H, t, CH2CH2OH), 3.94–3.95
(2H, m, CH2CH2N). Elemental analysis (%), calculated: C 49.975, N 14.576, H
−
10.412, found: C 49.913, N 14.603, H 10.457. IR: v = 3336, 2923, 2863, 1583, 1484,
1395, 1090, 957, 838 cm-1. (Yield 89% based on the amount of [Ch]Cl).
[Ch][β-Ala]. 1H NMR (300 MHz, D2O) δ: 2.29–2.31 (2H, t, CH2CH2NH2),
2.84–2.86 (2H, t, CH2CH2NH2), 3.09 (9H, s, (CH3)3N), 3.39–3.41 (2H, t,
CH2CH2OH), 3.93–3.95 (2H, m, CH2CH2N). Elemental analysis (%), calculated: C
−
49.975, N 14.576, H 10.412, found: C 49.936, N 14.529, H 10.403. IR: v = 3342,
2917, 2855, 1592, 1483, 1395, 1090, 957, 868 cm-1. (Yield 86% based on the amount
of [Ch]Cl).
[Ch][Ser]. 1H NMR (300 MHz, D2O) δ: 3.09 (9H, s, (CH3)3N), 3.30–3.33 (1H, dd,
CHNH2), 3.39–3.42 (2H, t, CH2CH2OH), 3.60–3.69 (2H, m, CHCH2OH), 3.93–3.97
(2H, m, CH2CH2N). Elemental analysis (%), calculated: C 46.154, N 13.462, H 9.616,
−
found: C 46.137, N 13.452, H 9.675. IR: v = 3392, 2918, 2855, 1592, 1482, 1399,
1087, 957, 868 cm-1. (Yield 82% based on the amount of [Ch]Cl).
[Ch][Pro]. 1H NMR (300 MHz, D2O) δ: 1.77–1.83 (3H, m, CH2CH2CH),
2.15–2.17 (1H, m, CH2CH2CH), 2.56–2.59 (1H, m, CH2NH), 2.95–3.00 (1H, m,
CH2NH), 3.09 (9H, s, (CH3)3N), 3.18–3.24 (1H, m, CHNH), 3.39–3.42 (2H, t,
CH2CH2OH), 3.93–3.97 (2H, m, CH2CH2N). Elemental analysis (%), calculated: C
−
55.046, N 12.844, H 10.092, found: C 55.179, N 12.808, H 10.116. IR: v = 3392,
3023, 2959, 2871, 1591, 1483, 1380, 1091, 957, 868 cm-1. (Yield 84% based on the
amount of [Ch]Cl).
Figure S1. FT-IR spectra of (a) [Ch][Gly], (b) [Ch][L-Ala], (c) [Ch][β-Ala], (d)
[Ch][Ser], (e) [Ch][Pro].
Figure S2. DSC curves for [Ch][Gly].
Figure S3. DSC curves for [Ch][L-Ala].
Figure S4. DSC curves for [Ch][β-Ala].
Figure S5. DSC curves for [Ch][Ser].
Figure S6. DSC curves for [Ch][Pro].
Figure S7. TGA and DTG curves for [Ch]Cl.
Figure S8. TGA and DTG curves for [Ch][Gly].
Figure S9. TGA and DTG curves for [Ch][L-Ala].
Figure S10. TGA and DTG curves for [Ch][β-Ala].
Figure S11. TGA and DTG curves for [Ch][Ser].
Figure S12. TGA and DTG curves for [Ch][Pro].