Stimuli-Responsive Vesicles and Hydrogels Formed by a Single-Tailed Dynamic Covalent Surfactant in Aqueous Solutions
Controlling the hierarchical self-assembly of surfactants in aqueous solutions has drawn much attention due to their broad range of applications, from targeted drug release, preparation of smart material, to biocatalysis. However, the synthetic procedures for surfactants with stimuli-responsive hydr...
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2024-10-01
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| author | Chunlin Xu Na Sun Huaixiu Li Xingchen Han Ailing Zhang Panpan Sun |
| author_facet | Chunlin Xu Na Sun Huaixiu Li Xingchen Han Ailing Zhang Panpan Sun |
| author_sort | Chunlin Xu |
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| description | Controlling the hierarchical self-assembly of surfactants in aqueous solutions has drawn much attention due to their broad range of applications, from targeted drug release, preparation of smart material, to biocatalysis. However, the synthetic procedures for surfactants with stimuli-responsive hydrophobic chains are complicated, which restricts the development of surfactants. Herein, a novel single-tailed responsive surfactant, 1-methyl-3-(2-(4-((tetradecylimino) methyl) phenoxy) ethyl)-3-imidazolium bromides (C<sub>14</sub>PMimBr), was facilely fabricated in situ by simply mixing an aldehyde-functionalized imidazolium cation (3-(2-(4-formylphenoxy) ethyl)-1-methyl imidazolium bromide, BAMimBr) and aliphatic amine (tetradecylamine, TDA) through dynamic imine bonding. With increasing concentration, micelles, vesicles, and hydrogels were spontaneously formed by the hierarchical self-assembly of C<sub>14</sub>PMimBr in aqueous solutions without any additives. The morphologies of vesicles and hydrogels were characterized by cryogenic transmission electron microscopy and scanning electron microscopy. The mechanical properties and microstructure information of hydrogels were demonstrated by rheological measurement, X-ray diffraction, and density functional theory calculation. In addition, the vesicles could be disassembled and reassembled with the breakage and reformation of imine bonds by adding acid/bubbling CO<sub>2</sub> and adding alkali. This work provides a simple method for constructing stimuli-responsive surfactant systems and shows great potential application in targeted drug release, drug delivery, and intelligent materials. |
| format | Article |
| id | doaj-art-2624a4630ad54e6ea8bd76f0aad066b1 |
| institution | Kabale University |
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| language | English |
| publishDate | 2024-10-01 |
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| series | Molecules |
| spelling | doaj-art-2624a4630ad54e6ea8bd76f0aad066b12024-11-08T14:37:58ZengMDPI AGMolecules1420-30492024-10-012921498410.3390/molecules29214984Stimuli-Responsive Vesicles and Hydrogels Formed by a Single-Tailed Dynamic Covalent Surfactant in Aqueous SolutionsChunlin Xu0Na Sun1Huaixiu Li2Xingchen Han3Ailing Zhang4Panpan Sun5School of Bioscience and Technology, Shandong Second Medical University, Weifang 261053, ChinaCollege of Pharmacy, Shandong Second Medical University, Weifang 261053, ChinaSchool of Bioscience and Technology, Shandong Second Medical University, Weifang 261053, ChinaSchool of Bioscience and Technology, Shandong Second Medical University, Weifang 261053, ChinaCollege of Chemical Engineering and Environmental Chemistry, Weifang University, Weifang 261061, ChinaSchool of Bioscience and Technology, Shandong Second Medical University, Weifang 261053, ChinaControlling the hierarchical self-assembly of surfactants in aqueous solutions has drawn much attention due to their broad range of applications, from targeted drug release, preparation of smart material, to biocatalysis. However, the synthetic procedures for surfactants with stimuli-responsive hydrophobic chains are complicated, which restricts the development of surfactants. Herein, a novel single-tailed responsive surfactant, 1-methyl-3-(2-(4-((tetradecylimino) methyl) phenoxy) ethyl)-3-imidazolium bromides (C<sub>14</sub>PMimBr), was facilely fabricated in situ by simply mixing an aldehyde-functionalized imidazolium cation (3-(2-(4-formylphenoxy) ethyl)-1-methyl imidazolium bromide, BAMimBr) and aliphatic amine (tetradecylamine, TDA) through dynamic imine bonding. With increasing concentration, micelles, vesicles, and hydrogels were spontaneously formed by the hierarchical self-assembly of C<sub>14</sub>PMimBr in aqueous solutions without any additives. The morphologies of vesicles and hydrogels were characterized by cryogenic transmission electron microscopy and scanning electron microscopy. The mechanical properties and microstructure information of hydrogels were demonstrated by rheological measurement, X-ray diffraction, and density functional theory calculation. In addition, the vesicles could be disassembled and reassembled with the breakage and reformation of imine bonds by adding acid/bubbling CO<sub>2</sub> and adding alkali. This work provides a simple method for constructing stimuli-responsive surfactant systems and shows great potential application in targeted drug release, drug delivery, and intelligent materials.https://www.mdpi.com/1420-3049/29/21/4984surfactantdynamic covalent bondresponsive vesicleaggregation behavior |
| spellingShingle | Chunlin Xu Na Sun Huaixiu Li Xingchen Han Ailing Zhang Panpan Sun Stimuli-Responsive Vesicles and Hydrogels Formed by a Single-Tailed Dynamic Covalent Surfactant in Aqueous Solutions Molecules surfactant dynamic covalent bond responsive vesicle aggregation behavior |
| title | Stimuli-Responsive Vesicles and Hydrogels Formed by a Single-Tailed Dynamic Covalent Surfactant in Aqueous Solutions |
| title_full | Stimuli-Responsive Vesicles and Hydrogels Formed by a Single-Tailed Dynamic Covalent Surfactant in Aqueous Solutions |
| title_fullStr | Stimuli-Responsive Vesicles and Hydrogels Formed by a Single-Tailed Dynamic Covalent Surfactant in Aqueous Solutions |
| title_full_unstemmed | Stimuli-Responsive Vesicles and Hydrogels Formed by a Single-Tailed Dynamic Covalent Surfactant in Aqueous Solutions |
| title_short | Stimuli-Responsive Vesicles and Hydrogels Formed by a Single-Tailed Dynamic Covalent Surfactant in Aqueous Solutions |
| title_sort | stimuli responsive vesicles and hydrogels formed by a single tailed dynamic covalent surfactant in aqueous solutions |
| topic | surfactant dynamic covalent bond responsive vesicle aggregation behavior |
| url | https://www.mdpi.com/1420-3049/29/21/4984 |
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