Novel sugar-based gemini surfactants with a 1,3-propan-2-ol spacer (1, 3-(N- alkyl-2-D-glucosaminyl acetyl) propan-2-ol, Glu(n)-3(OH)-Glu(n), n = 12, 14) were synthesized with D-(+)-glucono-1,5-lactone as starting material in two steps, whose structures were confirmed using proton nuclear magnetic resonance spectroscopy (1H NMR) and carbon nuclear magnetic resonance carbon spectroscopy (13C NMR). The micellization of Glu(n)-3(OH)-Glu(n) (n = 12, 14) in aqueous solution at 25.0°C was investigated by using surface tension measurement. The results show that the critical micelle concentration (CMC) of Glu(12)-3(OH)-Glu(12) is around 10–5 mol × L–1, and is one order of magnitude smaller than that of Glu(14)-3(OH)-Glu(14), indicating that the surface activity of Glu(12)-3(OH)-Glu(12) is superior to that of Glu(14)-3(OH)-Glu(14). Moreover, the aggregation behavior of Glu(12)-3(OH)-Glu(12) in aqueous solution at different pH values was investigated by surface tension, dynamic light scattering (DLS), and cryogenic transmission electron microscopic (Cryo-TEM) measurements. The results indicate that the CMC slightly increases with the decrease of the solution pH. The microstructure of Glu(12)-3(OH)-Glu(12) aggregates transitions from micelle to vesicle with the solution pH from acidic to neutral and alkaline. The microstructural transformation of Glu(12)-3(OH)-Glu(12) with the solution pH is mainly determined by the protonation of the two tertiary amine nitrogen atoms in its hydrophilic headgroups.

中文翻译：

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新型糖基 Gemini 表面活性剂在水溶液中的合成与聚集

具有 1,3-propan-2-ol 间隔基 (1, 3-(N-alkyl-2-D-glucosaminyl acetyl) propan-2-ol, Glu(n)-3(OH)) 的新型糖基双子表面活性剂-Glu(n), n = 12, 14) 以 D-(+)-glucono-1,5-lactone 为起始材料分两步合成，其结构通过质子核磁共振光谱 (1H NMR）和碳核磁共振碳光谱（13核磁共振）。通过使用表面张力测量研究了 Glu(n)-3(OH)-Glu(n) (n = 12, 14) 在 25.0°C 水溶液中的胶束化。结果表明Glu(12)-3(OH)-Glu(12)的临界胶束浓度(CMC)约为10–5摩尔×升–1, 比 Glu(14)-3(OH)-Glu(14) 小一个数量级，说明 Glu(12)-3(OH)-Glu(12) 的表面活性优于 Glu(12)-3(OH)-Glu(12) Glu(14)-3(OH)-Glu(14)。此外，通过表面张力、动态光散射 (DLS) 和低温透射电子显微镜 (Cryo-TEM) 研究了 Glu(12)-3(OH)-Glu(12) 在不同 pH 值水溶液中的聚集行为。测量。结果表明，随着溶液pH值的降低，CMC略有增加。Glu(12)-3(OH)-Glu(12) 的微观结构从胶束转变为囊泡，溶液的 pH 值从酸性变为中性和碱性。