Lyotropic Liquid Crystals in Amino acid derived Protic Ionic Liquids: Physicochemical Properties and Behaviour as Amphiphile Self-Assembly Media
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- Δάφνη Μνήμη Μιχαλολιάκος
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1 Lyotropic Liquid Crystals in Amino acid derived Protic Ionic Liquids: Physicochemical Properties and Behaviour as Amphiphile Self-Assembly Media Jiayi Wang, [a,b] Tamar L. Greaves, [b] Danielle F. Kennedy, [b] Asoka Weerawardena, [b] Gonghua Song, [a] Calum J. Drummond, [b] [a] Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology, Shanghai , P.R. China [b] CSIRO Materials Science and Engineering (CMSE), Private Bag 33, Clayton MDC, Vic 3169, Australia Characterization of PILs glycine ethyl ester nitrate (2-ethoxy-2-oxoethanaminium nitrate, GlyEN) 1 H NMR (d 6 -DMSO, 200 MHz): δ 8.28 (s, broad, 3H, NH 3 ), (m, 2H, OCH 2 ), 3.77 (d, J = 2.6 Hz, 2H, CH 2 ), 1.18 (t, J = 8 Hz, 3H, CH 3 ) ppm; 13 C NMR (d 6 - DMSO, 50 MHz): δ (COOH), 62.0 (OCH 2 CH 3 ), 40.2 (CH 2 ), 14.3 (OCH 2 CH 3 ) ppm; Calc. for C 4 H 10 N 2 O 5 C 28.92, H 6.07, N 16.86; Found C 27.55, H 5.98, N glycine ethyl ester formate (2-ethoxy-2-oxoethanaminium formate, GlyEF) 1 H NMR (d 6 -DMSO, 200 MHz): δ 8.30 (s, 2H), 7.57 (s, 3H, NH 3 + ), (m, 2H, OCH 2 ), 3.56 (s, 2H, CH 2 ), 1.18 (t, J = 8Hz, 3H, CH 3 ) ppm; 13 C NMR (d 6 -DMSO, 50 MHz): δ (HCO 2 - ), (cation C=O), 61.3 (OCH 2 CH 3 ), 41.2(CH 2 ), 14.4(OCH 2 CH 3 ); Calc. For C 5 H 11 NO 4 C 40.27, H 7.43, N 9.39; Found C 40.38, H 7.02, N glycine ethyl ester acetate (2-ethoxy-2-oxoethanaminium acetate, GlyEA) 1 H NMR (d 6 -DMSO, 200 MHz): δ 5.37 (s, 3H, NH 3 + ), (m, 2H, OCH 2 ), 3.28 (s, 2H, CH 2 ), 1.85 (s, 3H, anion CH 3 ), 1.17 (t, J = 6 Hz, 3H, cation CH 3 ) ppm; 13 C NMR (d 6 -DMSO, 50 MHz): δ (anion C=O), 172.7(cation C=O), 60.5 (OCH 2 CH 3 ), 43.5 (CH 2 ), 21.9 (CH 3 CO 2 - ), 14.5 (OCH 2 CH 3 ) ppm; Calc. Rapid decomposition at room temperature prohibited the microanalysis of this material. glycine ethyl ester (2-ethoxy-2-oxoethanaminium glycolate, GlyEG)
2 1 H NMR (d 6 -DMSO, 200 MHz): δ 4.73 (s, 3H, NH 3 + ), (m, 2H, OCH 2 ), 3.65 (m, 1H), 3.53 (s, 2H), (m, 2H), 1.18 (t, J = 9Hz, 3H) ppm; 13 C NMR (d 6 -DMSO, 50 MHz): δ (C=O), (C=O), 61.2 (CH 2 ), 61.0 (CH 2 ), 41.5 (CH 2 ), 14.4 (OCH 2 CH 3 ); Calc. For C 6 H 13 NO 5 C 40.22, H 7.31, N 7.82; Found C 39.32, H 7.25, N glycine ethyl ester lactate (2-ethoxy-2-oxoethanaminium lactate, GlyEL) 1 H NMR (d 6 -DMSO, 200 MHz): δ 5.1 (s, broad, 3H, NH 3 + ), (m, 2H, OCH 2 ), (m, 1H, CH), 3.65 (s, 2H, CH 2 ), (m, 2H, OCH 2 ), (m, 6H, CH 3 anion and cation) ppm; 13 C NMR (d 6 -DMSO, 50 MHz): δ (C=O), 174.5(C=O), 66.9 (CH), 61.1 (OCH 2 CH 3 ), 41.6 (CH 2 ), 21.3 (anion CH 3 ), 14.4 (OCH 2 CH 3 ); Calc. For C 7 H 15 NO 5 C 43.52, H 7.83, N 7.25; Found C 42.36, H 7.68, N Alanine methyl ester nitrate (1-methoxy-1-oxopropan-2-aminium nitrate, AlaMN) 1 H NMR (d 6 -DMSO, 200 MHz): δ 7.20 (s, broad, 3H, NH 3 + ), (m, 1H, CH), 3.71 (s, 3H, OCH 3 ), 1.35 (d, J = 4Hz, 3H, CH 3 ) ppm; 13 C NMR (d 6 -DMSO, 50 MHz): δ (C=O), 53.2 (CH), 48.4 (CH 3 ), 16.5 (OCH 3 ) ppm; Calc. For C 4 H 10 N 2 O 5 C 28.92, H 6.07, N 16.86; Found C 29.83, H 6.17, N Alanine methyl ester formate (1-methoxy-1-oxopropan-2-aminium formate, AlaMF) 1 H NMR (d 6 -DMSO, 200 MHz): δ 9.31 (s, 1H, HCO 2 - ), 7.34 (s, 3H, NH 3 + ), (m, 1H, CH), 3.65 (s, 3H, OCH 3 ), 1.27 (d, J = 3.6 Hz, 3H, CH 3 ) ppm; 13 C NMR (d 6 - DMSO, 50 MHz): δ (C=O), (C=O), 52.5 (CH), 48.8 (CH 3 ), 18.3 (OCH 3 ) ppm; Calc. For C 5 H 11 NO 4 C 40.27, H 7.43, N 9.39; Found C 39.82, H 7.55, N Alanine methyl ester acetate (1-methoxy-1-oxopropan-2-aminium acetate, AlaMA) 1 H NMR (d 6 -DMSO, 200 MHz): δ 5.47 (s, 1H NH 3 + ), 3.60 (s, 3H, OCH 3 ), (m, 1H, CH), 1.85 (s, 3H, anion CH 3 ), 1.17 (d, J = 3.4 Hz, 3H, CH 3 )) ppm; 13 C NMR (d 6 -DMSO, 50 MHz): δ (C=O), (C=O), 52.0 (CH), 49.6 (CH 3 ), 21.9 (CH 3 CO 2 - ), 20.4 (OCH 3 ) ppm; rapid conversion to the corresponding amide at room temperature prohibited the microanalysis of this material. NMR initially and after 3
3 months at 5 ºC shown below, Figure S1. Figure S1 1 H NMR spectra of AlaMA initially and after 3 months of storage. Alanine methyl ester glycolate (1-methoxy-1-oxopropan-2-aminium glycolate, AlaMG) 1 H NMR (d 6 -DMSO, 200 MHz): δ 5.82 (s, broad, 3H, NH 3 + ), (m, 1H, CH), 3.65 (s, 3H, CH 2 and OH), 3.14 (s, 3H, OCH 3 ), 1.28 (d, J = 4 Hz, 3H, CH 3 ) ppm; 13 C NMR (d 6 -DMSO, 50 MHz): δ 175.7(C=O), (C=O), 61.1 (CH 2 ), 52.5 (CH), 48.8 (CH 3 ), 18.1 (OCH 3 ); Calc. For C 6 H 13 NO 5 C 40.22, H 7.31, N 7.82; Found C 39.09, H 7.28, N 7.35 ppm. Alanine methyl ester lactate (1-methoxy-1-oxopropan-2-aminium lactate, AlaML) 1 H NMR (d 6 -DMSO, 200 MHz): δ 5.40 (s, broad, 3H, NH 3 + ), (m, 2H, anion and cation CH), 3.64 (s, 1H, anion OH), 3.15 (s, 3H, OCH 3 ), 1.25 (d, J = 3.5 Hz, 3H, anion CH 3 ), 1.14 (d, J = 3.4 Hz, 3H, CH 3 ) ppm; 13 C NMR (d 6 -DMSO, 50 MHz): δ (C=O), (C=O), 66.8 (CHOH), 52.4 (CH 2 ), 49.0 (CH 3 ), 21.3 (anion CH 3 ), 18.8 (OCH 3 ); Calc. For C 7 H 15 NO 5 C 43.52; H 7.83; N 7.25; Found C 42.54, H 7.89, N 6.82 ppm. Alanine ethyl ester nitrate (1-ethoxy-1-oxopropan-2-aminium nitrate, AlaEN)
4 1 H NMR (d 6 -DMSO, 200 MHz): δ 7.35 (s, broad, 3H, NH 3 + ), (m, 2H, CH 2 ), (m, 1H, CH), 1.34 (d, J = 4Hz, 3H, CH 3 ), 1.20 (t, J = 7.2Hz, 3H, OCH 3 ) ppm; 13 C NMR (d 6 -DMSO, 50 MHz): δ (C=O), 62.0 (OCH 2 CH 3 ), 48.5 (CH 2 ), 16.6 (CH 3 ), 14.3 (OCH 2 CH 3 ) ppm. Alanine ethyl ester formate (1-ethoxy-1-oxopropan-2-aminium formate, AlaEF) 1 H NMR (d 6 -DMSO, 200 MHz): δ 8.30 (s, 1H, HCO 2 - ), 7.22 (s, 3H, NH 3 + ), (m, 2H), (m, 1H, CH), 1.26 (d, J = 3.6Hz, 3H), 1.18 (t, J = 7Hz, 3H, OCH 3 ) ppm; 13 C NMR (d 6 -DMSO, 50 MHz): δ (C=O), (C=O), 61.2 (OCH 2 CH 3 ), 48.9 (CH 2 ), 18.45(CH 3 ), 14.4 (OCH 2 CH 3 ) ppm. Alanine ethyl ester acetate (1-ethoxy-1-oxopropan-2-aminium acetate, AlaEA) 1 H NMR (d 6 -DMSO, 200 MHz): δ 5.21 (s, 3H, NH 3 + ), (m, 2H, OCH 2 ), (m, 1H, CH), 1.85 (s, 3H, CH 3 ), (m, 6H, OCH 3 ) ppm; 13 C NMR (d 6 -DMSO, 50 MHz): δ (C=O), (C=O), 60.5 (OCH 2 CH 3 ), 49.7 (CH 2 ), 21.9 (CH 3 CO 2 - ), 20.4 (CH 3 ), (OCH 2 CH 3 ) ppm. Alanine ethyl ester glycolate (1-ethoxy-1-oxopropan-2-aminium glycolate, AlaEG) 1 H NMR (d 6 -DMSO, 200 MHz): δ 5.09 (s, broad, 3H, NH 3 + ), (m, 2H, OCH 2 ), 3.73 (s, 2H, anion CH 2 ), (m, 1H, CH), (m, 6H, OCH 3 ) ppm; 13 C NMR (d 6 -DMSO, 50 MHz): δ (C=O), (C=O), 61.0 (CH 2 or CH), 60.6 (CH 2 or CH), 49.2 (OCH 2 CH 3 ), 19.1 (CH 3 ), 14.5 (OCH 2 CH 3 ) ppm. Alanine ethyl ester lactate (1-ethoxy-1-oxopropan-2-aminium lactate, AlaEL) 1 H NMR (d 6 -DMSO, 200 MHz): δ 5.62 (s, broad, 3H, NH 3 + ), (m, 2H, CH 2 ), (m, 1H, anion or cation CH), (m, 1H, anion or cation CH), 3.15 (s, 1H, OH), (m, 9H, OCH 3, anion CH 3 and cation CH 3 ) ppm; 13 C NMR (d 6 - DMSO, 50 MHz): δ (C=O), (C=O), 66.7 (CHOH), 61.1 (OCH 2 CH 3 ), 49.0 (CH), 21.3 (anion CH 3 ), 18.8 (CH 3 ), 14.4 (OCH 2 CH 3 ) ppm; Calc. For C 8 H 17 NO 5 C 46.37; H 8.27; N 6.76; Found C 45.70, H 8.28, N 6.08.
5 Phenylalanine ethyl ester nitrate ((S)-1-ethoxy-1-oxo-3-phenylpropan-2-aminium nitrate, PheEN) 1 H NMR (d 6 -DMSO, 200 MHz): δ 7.99 (s, broad, 3H, NH 3 + ), (m, 5H, Ph), (m, 1H, CH), (m, 2H, OCH 2 ), (m, 2H, CH 2 Ph), 1.07 (t, J = 7.2 Hz, 3H, CH 3 ) ppm; 13 C NMR (d 6 -DMSO, 50 MHz): δ 169.9(C=O), (quat Ph), (o or m -Ph), (o or m -Ph), (p-ph), 62.0 (OCH 2 CH 3 ), 53.9 (CH), 37.0 (CH 2 Ph), 14.2 (OCH 2 CH 3 ); Calc. For C 11 H 16 N 2 O 5 C 51.56; H 6.29; N 10.93; Found C 52.61, H 6.53, N Phenylalanine ethyl ester formate ((S)-1-ethoxy-1-oxo-3-phenylpropan-2-aminium formate, PheEF) 1 H NMR (d 6 -DMSO, 200 MHz): δ 8.22 (s, 1H, HCO 2 - ), (m, 5H, Ph), 4.67 (s, 3H, NH 3 + ), (m, 1H, CH), 3.70 (t, J = 7.2 Hz, 2H, OCH 2 ), 2.87 (d, J = 3.4 Hz, 2H, CH 2 ), 1.07 (t, J = 7.2 Hz, 3H, CH 3 ) ppm; 13 C NMR (d 6 -DMSO, 50 MHz): δ (C=O), (C=O), (quat Ph), (o or m-ph), (o or m -Ph), (p-ph), 60.7 (OCH 2 CH 3 ), 55.5 (CH), 14.4 (OCH 2 CH 3 ) ppm N.B. CH 2 Ph peak not observed, under solvent peak; Calc. For C 12 H 17 NO 4 C 60.24; H 7.16; N 5.85; Found C 62.01, H 7.20, N Phenylalanine ethyl ester acetate ((S)-1-ethoxy-1-oxo-3-phenylpropan-2-aminium acetate, PheEA) 1 H NMR (d 6 -DMSO, 200 MHz): δ (m, 5H, Ph), (m, 5H, NH 3 + and CH 2 Ph), 3.53 (t, J = 6.8 Hz, 2H, OCH 2 ), (m, 1H, CH), 1.88 (s, 3H, anion CH 3 ), 1.08 (t, J = 6.8 Hz, 3H, OCH 2 CH 3 ) ppm; 13 C NMR (d 6 -DMSO, 50 MHz): δ (C=O), (C=O), (quat Ph), (o or m -Ph), (o or m -Ph), (p-ph), 60.3 (OCH 2 CH 3 ), 56.1 (CH), 21.6 (CH 3 CO 2 - ), 14.4 (OCH 2 CH 3 ) ppm N.B. CH 2 Ph peak not observed, under solvent peak; Calc. For C 13 H 19 NO 4 C 61.64; H 7.56; N 5.53; Found C 61.98, H 7.81, N Phenylalanine ethyl ester glycolate ((S)-1-ethoxy-1-oxo-3-phenylpropan-2-aminium glycolate, PheEG)
6 1 H NMR (d 6 -DMSO, 200 MHz): δ (m, 5H, Ph), 4.68 (s, 3H, NH 3 + ), (m, 2H, OCH 2 ), 3.78 (s, 2H, CH 2 anion), 3.72 (t, J = 6.8 Hz, 1H, CH), 2.88 (d, J = 3.4 Hz, 2H, CH 2 Ph), 1.07 (t, J = 6.8 Hz, 3H, OCH 2 CH 3 ) ppm; 13 C NMR (d 6 -DMSO, 50 MHz): δ (C=O), (C=O), (quat Ph), (o or m -Ph), (o or m -Ph), (p-ph), 60.8 (anion CH 2 or OCH 2 CH 3 ), 60.6 (anion CH 2 or OCH 2 CH 3 ), 55.4 (CH), 14.3 (OCH 2 CH 3 ) ppm N.B. CH 2 Ph peak not observed, under solvent peak; Calc. For C 13 H 19 NO 5 C 57.98; H 7.11; N 5.20; Found C 58.01, H 7.19, N Phenylalanine ethyl ester lactate ((S)-1-ethoxy-1-oxo-3-phenylpropan-2-aminium lactate, PheEL) 1 H NMR (d 6 -DMSO, 200 MHz): δ (m, 5H, Ph), 4.48 (s, broad, 3H, NH 3 + ), (m, 3H, OCH 2 and CHMe), 3.63 (t, J = 6.8 Hz, 1H, CH), 2.84 (d, J = 3.4 Hz, 2H, CH 2 Ph), (m, 3H, anion CH 3 ), 1.07 (t, J = 6.8 Hz, 3H, OCH 2 CH 3 ) ppm; 13 C NMR (d 6 -DMSO, 50 MHz): δ (C=O), (C=O), (quat Ph), (o or m -Ph), (o or m -Ph), (p-ph), 66.4(anion CH 2 or OCH 2 CH 3 ), 60.6 (anion CH 2 or OCH 2 CH 3 ), 55.7 (CH), 21.0 (anion CH 3 ), 14.4 (OCH 2 CH 3 ) ppm N.B. CH 2 Ph not observed, under solvent peak; Calc. For C 14 H 21 NO 5 C 59.35; H 7.47; N 4.94; Found C 60.09, H 7.63, N Proline methyl ester nitrate ((S)-2-(methoxycarbonyl)pyrrolidin-1-ium nitrate, ProMN) 1 H NMR (d 6 -DMSO, 200 MHz): δ 9.53 (s, 1H, N-H), 8.96 (s, 1H, N-H), 4.40 (t, J = 7.6 Hz, 1H, CH), 3.73 (s, 3H, CH 3 ), (m, 2H, CH 2 ), (m, 1H, CH 2 ), (m, 2H, CH 2 ) ppm; 13 C NMR (d 6 -DMSO, 50 MHz): δ (C=O), 59.1 (CH), 53.4 (CH 3 ), 46.0 (CH 2 ), 28.1 (CH 2 ), 23.5 (CH 2 ) ppm; Calc. For C 6 H 12 N 2 O 5 C 37.50; H 6.29; N 14.58; Found C 37.12, H 6.53, N Proline methyl ester formate ((S)-2-(methoxycarbonyl)pyrrolidin-1-ium formate, ProMF) 1 H NMR (d 6 -DMSO, 200 MHz): δ 8.97 (s, 2H), 8.27(s, 1H, HCO 2 - ), (m, 1H), 3.66 (s, 3H), (m, 2H), (m, 1H), (m, 3H) ppm; 13 C NMR (d 6 -DMSO, 50 MHz): δ (C=O), (C=O), 58.9 (CH), 52.6 (CH 3 ), 46.0 (CH 2 ), 29.1 (CH 2 ), 24.6 (CH 2 ); Calc. For C 7 H 13 NO 4 C 47.99; H 7.48; N 8.00; Found C 51.47, H 7.18, N 9.25.
7 Proline methyl ester acetate ((S)-2-(methoxycarbonyl)pyrrolidin-1-ium acetate, ProMA) 1 H NMR (d 6 -DMSO, 200 MHz): δ 7.25 (s, 2H), (m, 1H), 3.61 (s, 3H), (m, 2H), (m, 1H), 1.85 (s, 3H), (m, 3H) ppm; 13 C NMR (d 6 - DMSO, 50 MHz): δ (C=O), (C=O), 59.2 (CH), 52.0 (CH 3 ), 46.6 (CH 2 ), 29.8 (CH 2 ), 25.4 (CH 2 ), 21.8 (CH 3 CO 2 - ); Calc. For C 8 H 15 NO 4 C 50.78; H 7.99; N 7.40; Found C 50.11, H 7.69, N Proline methyl ester glycolate ((S)-2-(methoxycarbonyl)pyrrolidin-1-ium glycolate, ProMG) 1 H NMR (d 6 -DMSO, 200 MHz): δ 5.62 (s, 2H), (m, 1H), 3.63 (s, 3H), 3.15 (s, 1H), (m, 2H), (m, 1H), 1.85 (s, 3H), (m, 3H) ppm; 13 C NMR (d 6 -DMSO, 50 MHz): δ (C=O), (C=O), 60.4 (CH 2 anion), 59.1 (CH), 52.4 (CH), 46.3 (CH 2 ), 29.4 (CH 2 ), 25.0 (CH 2 ); Calc. For C 8 H 15 NO 5 C 46.82; H 7.37; N 6.83; Found C 44.20, H 7.46, N Proline methyl ester glycolate ((S)-2-(methoxycarbonyl)pyrrolidin-1-ium glycolate, ProMG) 1 H NMR (d 6 -DMSO, 200 MHz): δ 5.73 (s, 2H), (m, 2H), 3.64 (s, 3H), 3.15 (s, 1H), (m, 2H), (m, 1H), (m, 3H), 1.17 (d, J = 3.4Hz, 3H) ppm; 13 C NMR (d 6 -DMSO, 50 MHz): δ (C=O), (C=O), 60.4 (CH anion), 59.1 (CH), 52.4 (CH 2 ), 46.4 (CH 2 ), 29.5 (CH 2 ), 25.0 (CH 2 ); Calc. For C 9 H 17 NO 5 C 49.31; H 7.82; N 6.39; Found C 47.98, H 7.84, N 6.23.
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