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New Polyfunctional Biamphiphilic Surfactants Based on Alkylmethylmorpholinium Cation and Dodecyl Sulfate Anion

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Abstract

New biamphiphilic surfactants (BSs) have been synthesized based on alkylmethylmorpholinium cation and dodecyl sulfate anion (Mor-n(DS), n = 4, 6, 8, 10). The structure of the biamphiphiles has been characterized by IR spectroscopy, 1H NMR spectroscopy, mass spectrometry, and elemental analysis. The aggregation behavior of the biamphiphiles in aqueous solutions has been assessed by tensiometry, conductometry, fluorescence spectroscopy (using a pyrene probe) and dynamic and electrophoretic light scattering. It has been shown that an increase in the hydrophobic tail length by two carbon atoms in an amphiphilic cation leads to an increase in the surface activity of the surfactant by ~5 units and a decrease in the aggregation threshold of the systems by 1.5–2 times. It has been established that the formation of aggregates with hydrodynamic diameters of 20–120 nm depending on the alkyl chain length of the alkylmethylmorpholinium cation and BS concentration. The zeta potential of the systems ranges from –25 to –100 mV and decreases with increasing biamphiphile concentration. Spectrophotometry has been employed to show a significant solubilization capacity of the biamphiphiles with respect to a hydrophobic dye Orange OT. The compounds obtained may be of interest for biomedical applications and other high-tech areas.

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Funding

The work was supported by the Russian Science Foundation (project no. 23-73-01035).

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  1. Arbuzov Institute of Organic and Physical Chemistry, Federal Research Center, Kazan Scientific Center, Russian Academy of Sciences, 420088, Kazan, Russia

    D. M. Kuznetsov, D. A. Kuznetsova, F. G. Valeeva & L. Ya. Zakharova

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APPENDIX

APPENDIX

4-Butyl-4-methylmorpholinium dodecyl sulfate. Yield, 1.3 g (80.6%); M.p., 62–65°C. IR spectrum (KBr), (ν, cm–1): 3460, 2959, 2920, 2852, 1648, 1469, 1381, 1223, 1131, 1113, 1075, 1019, 992, 912, 896, 827, 724, 631, 586. 1H NMR spectrum (400 MHz, CDCl3, δ ppm, J Hz): 0.87 t (OSO\(_{3}^{ - }\)–(CH2)11–CH3, 3H, 3JHH 6.8); 1.00 t (N+–(CH2)3–CH3, 3H, 3JHH 7.3); 1.24–1.34 m (N+–(CH2)2–CH2–CH3, OSO\(_{3}^{ - }\)–(CH2)3(CH2)8– CH3, 18H); 1.42–1.48 m (OSO\(_{3}^{ - }\)–(CH2)2–CH2–(CH2)8–CH3, 2H); 1.60–1.67 m (OSO\(_{3}^{ - }\)–CH2-CH2–(CH2)9–CH3, 2H); 1.76 m (N+–CH2–CH2–CH2–CH3, 2H); 3.38 s (N+–CH3, 3H); 3.51 m (N+–CH2–(CH2)2–CH3, 2H); 3.59 – 3.69 two m (N+–CH2–CH2–O–, 4H); 3.96 – 4.09 two m (OSO\(_{3}^{ - }\)–CH2–(CH2)10–CH3, N+–CH2–CH2–O–, 6H). Found, %: C, 59.47; H, 10.74; N, 3.22; S, 7.48. Calculated for C21H45NO5S%: C, 59.54; H, 10.71; N, 3.31; S, 7.57. ESI mass spectrum, m/z: [M–C12H25OSO3]+ 158.05; [C12H25OSO3]– 265.14 (calc. m/z for C21H45NO5S 423.30).

4-Hexyl-4-methylmorpholinium dodecyl sulfate. Yield 1.1 g (71.4%). M.p. 87−92°C. IR spectrum (KBr), ν, cm–1: 3456, 2957, 2923, 2854, 1638, 1468, 1379, 1248, 1222, 1132, 1117, 1062, 999, 919, 900, 790, 724, 623, 580. NMR spectrum 1H (600 MHz, D2O, δ ppm, J Hz): 0.95 t (OSO\(_{3}^{ - }\)–(CH2)11–CH3, 3H, 3JHH 6.9); 1.00 t (N+–(CH2)5–CH3, 3H, 3JHH 6.9); 1.37–1.46 m (N+–(CH2)2–(CH2)3–CH3, OSO\(_{3}^{ - }\)–(CH2)2–(CH2)9–CH3, 24H); 1.74 m (OSO\(_{3}^{ - }\)–CH2–CH2–(CH2)9–CH3, 2H); 1.89 m (N+–CH2–CH2–(CH2)3–CH3, 2H); 3.28 s (N+–CH3, 3H); 3.53–3.63 m (N+–CH2–CH2–O–, N+–CH2–(CH2)4–CH3, 6H); 4.05 m (OSO\(_{3}^{ - }\)–CH2–(CH2)10–CH3, 2H); 4.12 m (N+–CH2–CH2–O–, 4H). Found, %: C, 61.08; H, 10.99; N, 3.10; S, 7.01. Calculated for C23H49NO5S%: C, 61.16; H, 10.93; N, 3.11; S, 7.10. ESI mass spectrum, m/z: [MC12H25OSO3]+ 186.15; [C12H25OSO3]– 265.12 (calc. m/z for C23H49NO5S 451.33).

4-Methyl-4-octylmorpholinium dodecyl sulfate. Yield 1.1 g (74.3%). M.p. 100–102°C. IR spectrum (KBr), ν, cm–1: 3447, 2957, 2924, 2853, 1637, 1468, 1439, 1379, 1251, 1226, 1120, 1096, 1061, 1016, 995, 913, 900, 857, 784, 723, 644, 62 2, 581, 536. NMR spectrum 1H (600 MHz, CDCl3, δ ppm, J Hz): 0.87 t (OSO\(_{3}^{ - }\)–(CH2)11–CH3, 3H, 3JHH 7.1); 0.88 t (N+–(CH2)7–CH3, 3H, 3JHH 7.1); 1.24–1.39 two m (N+–(CH2)2–(CH2)5–CH3, OSO\(_{3}^{ - }\)–(CH2)2–(CH2)9–CH3, 28Н); 1.64 m (OSO\(_{3}^{ - }\)–CH2–CH2–(CH2)9–CH3, 2H); 1.76 m (N+–CH2–CH2–(CH2)5–CH3, 2H); 3.38 s (N+–CH3, 3H); 3.48 m (N+–CH2–(CH2)6–CH3, 2H); 3.54–3.57, 3.66–3.68 two m (N+–CH2–CH2–O–, 4H); 3.95–3.99 m (N+–CH2–CH2–O–, 4H); 4.04–4.08 m (OSO\(_{3}^{ - }\)–CH2–(CH2)10–CH3, 2H). Found, %: C, 62.66; H, 11.15; N, 2.84; S, 6.60. Calculated for C25H53NO5S: C, 62.59; H, 11.13; N, 2.92; S, 6.68. ESI mass spectrum, m/z: [MC12H25OSO3]+ 214.03; [C12H25OSO3]– 265.14 (calc. m/z for C25H53NO5S 479.36).

4-Decyl-4-methylmorpholinium dodecyl sulfate. Yield 1.1 g (78%). M.p. 98–100°C. IR spectrum (KBr), ν, cm–1: 3489, 2957, 2922, 2853, 1640, 1469, 1381, 1248, 1227, 1120, 1061, 1015, 992, 904, 855, 786, 723, 623, 581. NMR spectrum 1H (400 MHz, CDCl3, δ ppm, J Hz): 0.86–0.89 t (OSO\(_{3}^{ - }\)–(CH2)11–CH3, N+–(CH2)9–CH3, 6H); 1.25–1.37 two m (N+–(CH2)2–(CH2)7–CH3, OSO3¯–(CH2)2–(CH2)9–CH3, 32Н); 1.65 m (OSO\(_{3}^{ - }\)–CH2–CH2–(CH2)9–CH3, 2H); 1.77 m (N+–CH2–CH2–(CH2)7–CH3, 2H); 3.38 s (N+–CH3, 3H); 3.48 m (N+–CH2–(CH2)8–CH3, 2H); 3.54–3.58, 3.65–3.69 two m (N+–CH2–CH2–O–, 4H); 3.95–4.01 m (N+–CH2–CH2–O–, 4H); 4.04–4.10 m (OSO\(_{3}^{ - }\)–CH2–(CH2)10–CH3, 2H). Found, %: C, 63.79; H, 11.28; N, 2.82; S, 6.24. Calculated for C27H57NO5S%: C, 63.86; H, 11.31; N, 2.76; S, 6.31. ESI mass spectrum, m/z: [MC12H25OSO3]+ 242.07; [C12H25OSO3]– 265.15 (calc. m/z for C27H57NO5S 507.40).

Fig. A1.
figure 7

1H NMR spectrum of Mor-4(DS).

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Fig. A2.
figure 8

ESI mass spectrum of Mor-4(DS) (registration of positive ions).

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Fig. A3.
figure 9

ESI mass spectrum of Mor-4(DS) (registration of negative ions).

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Fig. A4.
figure 10

IR spectrum of Mor-4(DS).

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Fig. A5.
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1H NMR spectrum of Mor-6(DS).

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Fig. A6.
figure 12

ESI mass spectrum of Mor-6(DS) (registration of positive ions).

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Fig. A7.
figure 13

ESI mass spectrum of Mor-6(DS) (registration of negative ions).

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Fig. A8.
figure 14

IR spectrum of Mor-6(DS).

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Fig. A9.
figure 15

1H NMR spectrum of Mor-8(DS).

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Fig. A10.
figure 16

ESI mass spectrum of Mor-8(DS) (registration of positive ions).

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Fig. A11.
figure 17

ESI mass spectrum of Mor-8(DS) (registration of negative ions).

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Fig. A12.
figure 18

IR spectrum of Mor-8(DS).

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Fig. A13.
figure 19

NMR 1H spectrum of Mor-10(DS).

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Fig. A14.
figure 20

ESI mass spectrum of Mor-10(DS) (registration of positive ions).

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Fig. A15.
figure 21

ESI mass spectrum of Mor-10(DS) (registration of negative ions).

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Fig. A16.
figure 22

IR spectrum of Mor-10(DS).

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Fig. A17.
figure 23

Dependence of specific electrical conductivity on concentration of biamphiphiles for (a) Mor-4(DS) and Mor-6(DS) systems and (b) Mor-8(DS) and Mor-10(DS) systems: (squares) Mor-4(DS), (rhombs) Mor-6(DS), (circles) Mor-8(DS), and (triangles) Mor-10(DS); 25°C.

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Fig. A18.
figure 24

Fluorescence spectra of pyrene measured in the presence of different amounts of quencher (CPB) for (a) 3, (b) 5, and (c) 7 mM Mor-4(DS); the arrow shows the direction of increasing quencher concentration.

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Fig. A19.
figure 25

Fluorescence spectra of pyrene measured in the presence of different amounts of quencher (CPB) for (a) 3, (b) 5, and (c) 7 mM Mor-6(DS); the arrow shows the direction of increasing quencher concentration.

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Fig. A20.
figure 26

Fluorescence spectra of pyrene measured in the presence of different amounts of quencher (CPB) for (a) 1, (b) 3, and (c) 5 mM Mor-8(DS); the arrow shows the direction of increasing quencher concentration.

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Fig. A21.
figure 27

Fluorescence spectra of pyrene measured in the presence of different amounts of quencher (CPB) for (a) 0.5, (b) 0.8, and (c) 1 mM Mor-10(DS); the arrow shows the direction of increasing quencher concentration.

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Fig. A22.
figure 28

Absorption spectra of OOT measured for Mor-n(DS)/OOT binary systems at different surfactant concentrations: (a) Mor-4(DS), (b) Mor-6(DS), (c) Mor-8(DS), and (d) Mor-10(DS); the arrow shows the direction of increasing surfactant concentration; 25°C.

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Kuznetsov, D.M., Kuznetsova, D.A., Valeeva, F.G. et al. New Polyfunctional Biamphiphilic Surfactants Based on Alkylmethylmorpholinium Cation and Dodecyl Sulfate Anion. Colloid J 86, 64–85 (2024). https://doi.org/10.1134/S1061933X23601051

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