Новые полифункциональные биамфифильные ПАВ на основе алкилметилморфолиния и додецилсульфат-аниона

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Abstract

Синтезированы новые биамфифильные поверхностно-активные вещества (БПАВ) на основе катиона алкилметилморфолиния и додецилсульфат-аниона (Мор-n(ДС), n = 4, 6, 8, 10). С привлечением методов ИК-спектроскопии, спектроскопии ЯМР 1Н, масс-спектрометрии, элементного анализа охарактеризована структура биамфифилов. Методами тензиометрии, кондуктометрии, флуоресцентной спектроскопии (с использованием зонда пирена), динамического и электрофоретического рассеяния света проведена оценка агрегационного поведения биамфифилов в водных растворах. Показано, что увеличение длины углеводородного радикала на два углеродных атома у амфифильного катиона приводит к увеличению поверхностной активности ПАВ ~ на 5 единиц и к снижению порога агрегации систем в 1.5–2 раза. Установлено, что происходит формирование агрегатов с гидродинамическим диаметром 20–120 нм в зависимости от длины радикала у катиона алкилметилморфолиния и от концентрации БПАВ. Дзета-потенциал систем находится в диапазоне от –25 до –100 мВ и снижается с увеличением концентрации биамфифилов. Методом спектрофотомерии показана значительная солюбилизационная способность биамфифилов по отношению к гидрофобному красителю Оранж ОТ. Полученные соединения могут представлять интерес для биомедицинского применения и других высокотехнологичных направлений.

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Д. М. Кузнецов

Институт органической и физической химии им. А. Е. Арбузова ФИЦ Казанский научный центр РАН

Author for correspondence.
Email: kuznetsov_denis91@mail.ru
Russian Federation, 420088, Казань, ул. Акад. Арбузова, 8

Д. А. Кузнецова

Институт органической и физической химии им. А. Е. Арбузова ФИЦ Казанский научный центр РАН

Email: kuznetsov_denis91@mail.ru
Russian Federation, 420088, Казань, ул. Акад. Арбузова, 8

Ф. Г. Валеева

Институт органической и физической химии им. А. Е. Арбузова ФИЦ Казанский научный центр РАН

Email: kuznetsov_denis91@mail.ru
Russian Federation, 420088, Казань, ул. Акад. Арбузова, 8

Л. Я. Захарова

Институт органической и физической химии им. А. Е. Арбузова ФИЦ Казанский научный центр РАН

Email: kuznetsov_denis91@mail.ru
Russian Federation, 420088, Казань, ул. Акад. Арбузова, 8

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Supplementary files

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2. Fig. 1. Isotherms of surface tension of aqueous solutions of biamphiphiles Mor-n(DS): black square – Mor-4(DS), black rhombus – Mor-6(DS), black circle – Mor-8(DS), black triangle – Mor-10(DS); 25°C.

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3. Fig. 2. Dependence of the ratio of fluorescence intensities of the first (373 nm) and third (384 nm) vibrational peaks of pyrene on the concentration of biamphiphiles for binary systems Mor-n(DS)/pyrene: black square – Mor-4(DS), black rhombus – Mor-6(DS), black circle – Mor-8(DS), black triangle – Mor-10(DS); 25°C.

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4. Fig. 3. The size distribution of aggregates, averaged by the number of particles, for aqueous solutions of Mor-n(DS): a) Mor-4(DS); b) Mor-6(DS); c) Mor-8(DS); d) Mor-10(DS); 25°C.

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5. Fig. 4. Dependence of the electrokinetic potential of aqueous solutions of Mor-n(DS) on the concentration of biamphiles: black square – Mor-4(DS), black rhombus – Mor-6(DS), black circle – Mor-8(DS), black triangle – Mor-10(DS); 25°C.

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6. Fig. 5. The dependence of the optical density of Orange on the concentration of BPAV for binary systems Mor-n(DS) at a wavelength of 495 nm/Orange FROM: black square – Mor-4(DS), black rhombus – Mor-6(DS), black circle – Mor-8(DS), black triangle – Mor-10(DS); 25 °C.

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7. Fig. 6. Values of the solubilization capacity of micelles for various amphiphilic systems.

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8. Fig. P1. NMR 1H spectrum of the compound Mor-4(DS).

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9. Fig. P2. Mass spectrum of the IER compound Mor-4(D C) (registration of positive ions).

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10. Fig. P3. Mass spectrum of the IER compound Mor-4(D C) (registration of negative ions).

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11. Fig. P4. IR spectrum of the Mor-4(DS) compound.

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12. Fig. P5. NMR 1H spectrum of the compound Mor-6(DS).

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13. Fig. P6. Mass spectrum of the IER compound Mor-6(D C) (registration of positive ions).

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14. Fig. P7. Mass spectrum of the IER compound Mor-6(D C) (registration of negative ions).

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15. Fig. P8. The IR spectrum of the Mor-6 compound (DS).

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16. Fig. P9. NMR 1H spectrum of the compound Mor-8(DS).

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17. Fig. P10. The mass spectrum of the IER compound Mor-8(D C) (registration of positive ions).

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18. Fig. P11. Mass spectrum of the IER compound Mor-8(D C) (registration of negative ions).

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19. Fig. P12. IR spectrum of the Mor-8(DS) compound.

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20. Fig. P13. NMR 1H spectrum of the compound Mor-10(DS).

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21. Fig. P14. Mass spectrum of the IER compound Mor-10(D C) (registration of positive ions).

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22. Fig. P15. The mass spectrum of the IER compound Mor-10(D C) (registration of negative ions).

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23. Fig. P16. IR spectrum of the Mor-10(DS) compound.

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24. Fig. P17. Dependence of specific electrical conductivity on the concentration of biamphiles: a) for systems Mor-4(DS) and Mor-6 (DS); b) for systems Mor-8(DS) and Mor-10(DS); black square – Mor-4(DS), black diamond – Mor-6(DS), black circle – Mor-8(DS), black triangle – Mor-10(DS); 25°C.

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25. Fig. P18. Pyrene fluorescence spectra in the presence of various amounts of extinguisher (SPB) for 3 mM (a), 5 m (b) and 7 mM (c) Mor-4(DS); the arrow shows the direction of increase in the concentration of the extinguisher.

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26. Fig. P19. Pyrene fluorescence spectra in the presence of various amounts of extinguisher (SPB) for 3 mM (a), 5 m (b) and 7 mM (c) Mor-6(DS); the arrow shows the direction of increase in the concentration of the extinguisher.

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27. Fig. P20. Pyrene fluorescence spectra in the presence of various amounts of extinguisher (SPB) for 1 mM (a), 3 m (b) and 5 mM (c) Mor-8 (DS); the arrow shows the direction of increase in the concentration of the extinguisher.

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28. Fig. P21. Pyrene fluorescence spectra in the presence of various amounts of extinguisher (SPB) for 0.5 mM (a), 0.8 m (b) and 1 mM (c) Mor-10(DS); the arrow shows the direction of increase in the concentration of the extinguisher.

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29. Fig. P22. Orange OT absorption spectra for binary systems Mor-n(DS)/Orange FROM at different concentrations of surfactants: a) Mor-4(DS); b) Mor-6(DS); c) Mor-8(DS); d) Mor-10(DS); the arrow shows an increase in the concentration of surfactants; 25 ° C.

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