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Study on the mechanism of the effect of coumaric acid with different hydroxyl substituent positions on constructing light-regulated wormlike micelles
Journal of Molecular Liquids ( IF 6 ) Pub Date : 2020-06-30 , DOI: 10.1016/j.molliq.2020.113710
Zhihu Yan , Feng Qian , Haonan Sun , Xia Lu , Yu Li , Haibin Lv , Caili Dai , Minglian Jiao

Light-regulated wormlike micelles have unique physicochemical properties and application prospects, therefore it has been widely studied in recent years. The interesting phenomenon of trans coumaric acid isomerides exhibits different solution properties deserves in-depth research when compounded with different types of surfactant. In this work, a pyrrolidinium-based surface active ionic liquids and trans coumaric acid isomerides, including trans ortho-coumaric acid (TOCA), trans meta-coumaric acid (TMCA) and trans para-coumaric acid (TPCA), are employed to construct a series of light-regulated wormlike micelles. The rheology, cryogen transmission electron microscopy (cryo-TEM), UV–vis spectra, 1H NMR and the DFT theory demonstrated that the structure of micelles in solution changed before and after UV light irradiation. Besides, the mechanism of trans coumaric acid isomerides (TOCA, TMCA, and TPCA) exhibits different solution properties that can be explained as follow. When the type of surfactant is cationic, the order of the spacer distance between the carboxyl group and the hydroxyl group is TPCA > TMCA > TOCA. Therefore, TOCA has the strongest ability to reduce the effective headgroup area of cationic surfactant, thereby greatly promoting the growth of wormlike micelles. When the type of surfactant is zwitterionic, under the combined action of hydrogen bonding and electrostatic attraction, trans coumaric acid isomerides are more prone to exhibit a vertical structure inside the lecithin head group. The order of capable of hydrogen bonding is TPCA > TMCA > TOCA, which explains TPCA can promote the micelles growth but TMCA and TOCA do not have this effect. The above theoretical discussion explains why trans coumaric acid isomerides exhibit different solution properties when compounded with different surfactants.



中文翻译:

不同羟基取代位置香豆酸构建光调节蠕虫状胶束作用机理的研究

光调节的蠕虫状胶束具有独特的理化性质和应用前景,因此近年来受到了广泛的研究。当与不同类型的表面活性剂混合使用时,反式香豆酸异构体的有趣现象表现出不同的溶液性质,值得深入研究。在这项工作中,基于吡咯烷鎓的表面活性离子液体和反式香豆酸异构体,包括反式邻香豆酸(TOCA),反式间香豆酸(TMCA)和反式对香豆酸(TPCA),被用于构建一系列光调节的蠕虫状胶束。流变学,冷冻剂透射电子显微镜(cryo-TEM),UV-vis光谱,11 H NMR和DFT理论表明,溶液中胶束的结构在紫外线照射前后发生了变化。此外,反式香豆酸异构体(TOCA,TMCA和TPCA)的机理表现出不同的溶液性质,可以解释如下。当表面活性剂的类型为阳离子时,羧基和羟基之间的间隔距离的顺序为TPCA> TMCA> TOCA。因此,TOCA具有最强的减少阳离子表面活性剂有效头基面积的能力,从而极大地促进了蠕虫状胶束的生长。当表面活性剂类型为两性离子时,在氢键和静电吸引的共同作用下,反式香豆酸异构体更易于在卵磷脂头基内部显示出垂直结构。能够氢键结合的顺序是TPCA> TMCA> TOCA,这说明TPCA可以促进胶束的生长,但是TMCA和TOCA没有这种作用。以上理论讨论解释了为什么反式香豆酸异构体与不同的表面活性剂混合时会表现出不同的溶液性质。

更新日期:2020-07-06
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