一种含偶氮苯的二肽表面活性剂的合成及自组装行为

doi:10.3969/j.issn.2097-2806.2024.05.002

Abstract

Abstract:

A glycylglycine-derived surfactant containing an azobenzene moiety as terminal （Azo-C₆-GG） was synthesized. Azo-C₆-GG self-assembled into vesicles driven by several non-covalent interactions. The trans-azobenzene transformed to cis-azobenzene after the irradiation of UV light, and vesicles were still formed in this cis-Azo-C₆-GG system. A supra-amphiphile （Azo-C₆-GG@α-CD） was formed after the addition of α-cyclodextrin （α-CD）, which formed vesicles in aqueous solution. The azobenzene group was embedded into the cavity of α-CD, and meanwhile, the CD ring shuttled between the alkyl chain and the azobenzene group. After the UV light irradiation, the alkyl chain was embedded into the cavity of α-CD. The Azo-C₆-GG@α-CD complexes were found to self-assemble into vesicles both before and after the UV light irradiation.

Key words: azobenzene, cyclodextrin, light irradiation, vesicle, self-assembly

CLC Number:

TQ423

Linlin Zhao, Yutian Jiao, Li Zhao, Ce Wang, Baocai Xu. Synthesis and self-assembly of an azobenzene-containing dipeptide surfactant[J].China Surfactant Detergent & Cosmetics, 2024, 54(5): 507-513.

Figures/Tables 8

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References 19

[1]	Hao Shanshan, Zhao Li, Xu Baocai. Synthesis of cholesterol derivative based amphiphilic molecules and their aggregation behavior[J]. China Surfactant Detergent & Cosmetics, 2016, 46 (5) : 243-246.
[2]	Ercole F, Davis T P, Evans R A. Photo-responsive systems and biomaterials: photochromic polymers, light-triggered self-assembly, surface modification, fluorescence modulation and beyond[J]. Polymer Chemistry, 2010, 1 (1) : 37-54.
[3]	Zhang Yunlai, Chang Rong, Duan Huazhen, et al. Metal ion and light sequentially induced sol-gel-sol transition of a responsive peptide-hydrogel[J]. Soft Matter, 2020, 16 (33) : 7652-7658. doi: 10.1039/d0sm00442a pmid: 32797141
[4]	Bian Tong, Chu Zonglin, Klajn Rafal. The many ways to assemble nanoparticles using light[J]. Advanced Materials, 2020, 32 (20) : e1905866.
[5]	Cheng Weinan, Zhao Dongxu, Qiu Yuan, et al. Robust multi-responsive supramolecular hydrogel based on a mono-component host-guest gelator[J]. Soft Matter, 2018, 14: 5213-5221. doi: 10.1039/c8sm00639c pmid: 29808224
[6]	Li Zhiyong, Shi Yunlei, Zhu Anlian, et al. Light-responsive, reversible emulsification and demulsification of oil-in-water pickering emulsions for catalysis[J]. Angewandte Chemie International Edition, 2021, 60 (8) : 3928-3933.
[7]	Guo Huichuang, Jiang Bing, Zhou Juntan, et al. Self-assembly of beta-cyclodextrin-derived amphiphile with a photo responsive guest[J]. Colloids and Surfaces A, 2019, 579: 123683.
[8]	Liu Yu, Zhao Linlin, Zhao Li, et al. Multi-stimuli-responsive supramolecular hydrogel based on an oxidized glutathione derivative[J]. Dyes and Pigments, 2022, 205: 110552.
[9]	Hao Shanshan, Zhao Qiaoya, Zhao Li, et al. Self-assembly and photo regulation of a supra-amphiphile based on host-guest interaction[J]. China Surfactant Detergent & Cosmetics, 2017, 47 (1) : 1-6.
[10]	Wang Chen, Fadeev Michael, Zhang Junji, et al. Shape-memory and self-healing functions of DNA-based carboxymethyl cellulose hydrogels driven by chemical or light triggers[J]. Chemical Science, 2018, 9 (35) : 7145-7152. doi: 10.1039/c8sc02411a pmid: 30310637
[11]	Lin Yinyang, Wang Aadong, Qiao Yan, et al. Rationally designed helical nanofibers via multiple non-covalent interactions: fabrication and modulation[J]. Soft Matter, 2010, 6 (9) : 2031-2036.
[12]	Wang Yapei, Ma Ning, Wang Zhiqiang, et al. Photocontrolled reversible supramolecular assemblies of an azobenzene-containing surfactant with alpha-cyclodextrin[J]. Angewandte Chemie International Edition, 2007, 46 (16) : 2823-2826.
[13]	Ten Cate A T, Dankers P Y W, Kooijman H, et al. Enantioselective cyclization of racemic supramolecular polymers[J]. Journal of the American Chemical Society, 2003, 125 (23) : 6860-6861. pmid: 12783526
[14]	Lin Yiyang, Cheng Xinhao, Qiao Yan, et al. Creation of photo-modulated multi-state and multi-scale molecular assemblies via binary-state molecular switch[J]. Soft Matter, 2010, 6 (5) : 902-908.
[15]	Jiang Jianzhong, Wang Guozheng, Ma Yuxuan, et al. Smart worm-like micelles responsive to CO₂/N₂ and light dual stimuli[J]. Soft Matter, 2017, 13 (15) : 2727-2732. doi: 10.1039/c7sm00185a pmid: 28224157
[16]	Zou Hui, Yuan Weizhong, Lu Yeqiang, et al. UV light-and thermo-responsive supramolecular aggregates with tunable morphologies from the inclusion complexation of dendritic/linear polymers[J]. Chemical Communications, 2017, 53 (16) : 2463-2466. doi: 10.1039/c6cc09959a pmid: 28180222
[17]	Jiang Lingxiang, Deng Manli, Wang Yilin, et al. Special Effect of β-cyclodextrin on the aggregation behavior of mixed cationic/anionic surfactant systems[J]. The Journal of Physical Chemistry B, 2009, 113 (21) : 7498-7504.
[18]	Harada A, Takashima Y, Nakahata M. Supramolecular polymeric materials via cyclodextrin-guest interactions[J]. Accounts of Chemical Research, 2014, 47 (7) : 2128-2140. doi: 10.1021/ar500109h pmid: 24911321
[19]	Guo Huichuang, Yang Jingxuan, Zhou Juntan, et al. Photoresponsive self-assembly of a beta-cyclodextrin derivative with an azobenzene terminal group in water[J]. Dyes and Pigments, 2018, 149: 626-632.

Synthesis and self-assembly of an azobenzene-containing dipeptide surfactant

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