Aggregation behavior of imidazolium-based chiral surfactant in aqueous solution |
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Authors: | Hejun Gao Lijuan Shi Shaohua Zhang Jun Li Xiaodong Wang Liqiang Zheng |
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Institution: | 1. Key Laboratory of Colloid and Interface Chemistry, Shandong University, Ministry of Education, Jinan, 250100, China 2. Chemical Synthesis and Pollution Control Key Laboratory of Sichuan Province, China West Normal University, Nanchong, 637000, China 3. Shandong Provincial Analysis and Test Center, Jinan, 250100, China
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Abstract: | A novel imidazolium-based chiral surfactant with a Y-type hydrophobic chain, (S)-(+)-1-(2,3-bis(octanoyloxy)propyl)-3-methylimidazolium chloride (Bopmim]Cl), was synthesized. The aggregation behavior of Bopmim]Cl in aqueous solution was then investigated by surface tension, electrical conductivity, 1H NMR, and fluorescence measurements. Compared with C12mim]Cl, the critical micelle concentration for Bopmim]Cl is lower, indicating that the novel chiral surfactant has superior capacity to form micelles. A larger value of pC 20, a greater minimum area per surfactant molecule (A min), a smaller degree of counterion binding (β), and a looser aggregate are caused by the relatively larger Y-type hydrophobic chain of Bopmim]Cl. Furthermore, analysis of the 1H NMR spectra revealed that the introduced Y-type hydrophobic chain may prevent the hydrophobic group from forming an extended chain configuration and cause a changeover from trans to gauche conformations upon micellization. The micelles of the novel chiral surfactant may provide some potential applications in the stereochemical recognition of surfaces or of biological structures. |
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