Citation: Di Zhao, Yong Chen, Yu Liu. Comparative studies on molecular induced aggregation of hepta-imidazoliumyl-β-cyclodextrin towards anionic surfactants[J]. Chinese Chemical Letters, ;2015, 26(7): 829-833. doi: 10.1016/j.cclet.2014.11.028 shu

Comparative studies on molecular induced aggregation of hepta-imidazoliumyl-β-cyclodextrin towards anionic surfactants

1.
Department of Chemistry, State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300071, China

Corresponding author: Yu Liu,
Received Date: 29 September 2014
Available Online: 29 October 2014
Fund Project: We thank 973 Programme (No. 2011CB932502) (No. 2011CB932502)

A b-cyclodextrin derivative bearing seven cationic arms and its singly charged analogue, i.e., per-6- deoxy-6-(1-methylimidazol-3-ium-3-yl)-β-cyclodextrin (3) and mono-6-deoxy-6-(1-methylimidazol-3-ium-3-yl)-β-cyclodextrin (4) were synthesized and fully characterized. Their induced aggregation behaviours towards two anionic surfactant, that is, sodium dodecyl sulfonate (SDS) and dioctyl sodium sulfosuccinate (Aerosol OT, AOT), were investigated by UV-vis, NMR, Zeta-potential, dynamic light scattering (DLS), and transmission electron microscopy. The results revealed that host 3 can induce the molecular aggregation of anionic surfactant at concentration far lower than its original CAC, leading to the larger diameter, the narrower size distribution and the higher thermal stability of the induced aggregate towards the anionic surfactant possessing more hydrophobic tails.
- Cyclodextrin,
- Surfactant,
- Molecular assembly,
- Induced aggregation
1. [1]
  [1] X. Zhang, C. Wang, Supramolecular amphiphiles, Chem. Soc. Rev. 40 (2011) 94– 101.
2. [2]
  [2] (a) Y. Wang, N. Ma, Z. Wang, X. Zhang, Photocontrolled reversible supramolecular assemblies of an azobenzene-containing surfactant with a-cyclodextrin, Angew. Chem. Int. Ed. 46 (2007) 2823–2826; (b) H.B. Cheng, H.Y. Zhang, Y. Liu, Dual-stimulus luminescent lanthanide molecular switch based on an unsymmetrical diarylperfluorocyclopentene, J. Am. Chem. Soc. 135 (2013) 10190–10193; (c) K. Wang, D.S. Guo, Y. Liu, Temperature-controlled supramolecular vesicles modulated by p-sulfonatocalix[5]arene with pyrene, Chem.: Eur. J. 16 (2010) 8006–8011; (d) Y.J. Jeon, P.K. Bharadwaj, S. Choi, J.W. Lee, K. Kim, Supramolecular amphiphiles: spontaneous formation of vesicles triggered by formation of a chargetransfer complex in a host, Angew. Chem. Int. Ed. 41 (2002) 4474–4476; (e) Y. Wang, H. Xu, X. Zhang, Tuning the amphiphilicity of building blocks: controlled self-assembly and disassembly for functional supramolecular materials, Adv. Mater. 21 (2009) 2849–2864; (f) Y. Cao, X.Y. Hu, Y. Li, et al., Multistimuli-responsive supramolecular vesicles based on water-soluble pillar[6]arene and SAINT complexation for controllable drug release, J. Am. Chem. Soc. 136 (2014) 10762–10769; (g) D.S. Guo, K. Wang, Y.X. Wang, Y. Liu, Cholinesterase-responsive supramolecular vesicle, J. Am. Chem. Soc. 134 (2012) 10244–10250.
3. [3]
  [3] D.S. Guo, Y. Liu, Supramolecular chemistry of p-sulfonatocalix[n]arenes and its biological applications, Acc. Chem. Res. 47 (2014) 1925–1934.
4. [4]
  [4] H. Zhang, X. Ma, K.T. Nguyen, Y. Zhao, Biocompatible pillararene-assembly-based carriers for dual bioimaging, ACS Nano 7 (2013) 7853–7863.
5. [5]
  [5] (a) U. Rauwald, O.A. Scherman, Supramolecular block copolymers with cucurbit[ 8]uril in water, Angew. Chem. Int. Ed. 47 (2008) 3950–3953; (b) J. Li, L. Zhou, Q. Luo, et al., Cucurbit[7]uril-based vesicles formed by self-assembly of supramolecular amphiphiles, Chin. J. Chem. 30 (2012) 2085– 2090.
6. [6]
  [6] (a) R.X. Li, S.M. Liu, J.Q. Zhao, H. Otsuka, A. Takahara, Preparation and characterization of cross-linked b-cyclodextrin polymer/Fe3O4 composite nanoparticles with core-shell structures, Chin. Chem. Lett. 22 (2011) 217–220; (b) L.H. Wang, Z.J. Zhang, H.Y. Zhang, H.L. Wu, Y. Liu, A twin-axial[5]pseudorotaxane based on cucurbit[8]uril and a-cyclodextrin, Chin. Chem. Lett. 24 (2013) 949–952; (c) Z. He, Z. Wang, H. Zhang, et al., Doxycycline and hydroxypropyl-β-cyclodextrin complex in poloxamer thermal sensitive hydrogel for ophthalmic delivery, Acta Pharm. Sin. B 1 (2011) 254–260; (d) S.S. Zhai, Y. Chen, Y. Liu, Selective binding of bile salts by b-cyclodextrin derivatives with appended quinolyl arms, Chin. Chem. Lett. 24 (2013) 442–446.
7. [7]
  [7] T. Bojinova, Y. Coppel, N. Lauth-de Viguerie, et al., Complexes between b-cyclodextrin and aliphatic guests as newnoncovalent amphiphiles: formation and physicochemical studies, Langmuir 19 (2003) 5233–5239.
8. [8]
  [8] A. Gadelle, J. Defaye, Selective halogenation at primary positions of cyclomaltooligosaccharides and a synthesis of per-3,6-anhydro cyclomaltooligosaccharides, Angew. Chem. Int. Ed. Engl. 30 (1991) 78–80.
9. [9]
  [9] B. Brady, N. Lynam, T.O. Sullivan, et al., 6A-O-p-Toluenesulfonyl-β-cyclodextrin, Org. Synth. 10 (2004) 77–79.
10. [10]
  [10] (a) J.E. Bujake, E.D. Goddard, Surface composition of sodium lauryl sulphonate and sulphate solutions by foaming and surface tension, Trans. Faraday Soc. 61 (1965) 190–195; (b) H.Z. Yuan, L.F. Shen, Y.R. Du, S. Zhao, J.Y. Yu, Micellization of sodium dodecyl sulfonate and Triton X-100 in polyacrylamide water solution studied by 1H NMR relaxation and two-dimensional nuclear overhauser enhancement spectroscopy, Colloid Polym. Sci. 277 (1999) 1026–1032; (c) A. Chatterjee, S.P. Moulik, S.K. Sanyal, B.K. Mishra, P.M. Puri, Thermodynamics of micelle formation of ionic surfactants: a critical assessment for sodium dodecyl sulfate, cetyl pyridinium chloride and dioctyl sulfosuccinate (Na salt) by microcalorimetric, conductometric, and tensiometric measurements, J, Phys. Chem. B 105 (2001) 12823–12831.
1. [1]
  Yu-Hui Zhang , Ye Tian , Xianliang Sheng , Chen-Shuang Liu , Lu-Qiang Wei , Jie Wang , Yong Chen . Construction of a black phosphorous-based noncovalent multiple nanosupramolecular assembly for synergistic targeted photothermal and chemodynamic therapy. Chinese Chemical Letters, 2025, 36(4): 110193-. doi: 10.1016/j.cclet.2024.110193
2. [2]
  Siwei Wang , Wei-Lei Zhou , Yong Chen . Cucurbituril and cyclodextrin co-confinement-based multilevel assembly for single-molecule phosphorescence resonance energy transfer behavior. Chinese Chemical Letters, 2024, 35(12): 110261-. doi: 10.1016/j.cclet.2024.110261
3. [3]
  Yongmin Zhang , Shuang Guo , Mingyue Zhu , Menghui Liu , Sinong Li . Design and Improvement of Physicochemical Experiments Based on Problem-Oriented Learning: a Case Study of Liquid Surface Tension Measurement. University Chemistry, 2024, 39(2): 21-27. doi: 10.3866/PKU.DXHX202307026
4. [4]
  Congying Lu , Fei Zhong , Zhenyu Yuan , Shuaibing Li , Jiayao Li , Jiewen Liu , Xianyang Hu , Liqun Sun , Rui Li , Meijuan Hu . Experimental Improvement of Surfactant Interface Chemistry: An Integrated Design for the Fusion of Experiment and Simulation. University Chemistry, 2024, 39(3): 283-293. doi: 10.3866/PKU.DXHX202308097
5. [5]
  Yukai Jiang , Yihan Wang , Yunkai Zhang , Yunping Wei , Ying Ma , Na Du . Characterization and Phase Diagram of Surfactant Lyotropic Liquid Crystal. University Chemistry, 2024, 39(4): 114-118. doi: 10.3866/PKU.DXHX202309033
6. [6]
  Yi Fan , Zhuoqi Jiang , Zhipeng Li , Xuan Zhou , Jingan Lin , Laiying Zhang , Xu Hou . 偶极诱导液体门控可视化物质检测——化学“101计划”表界面性质应用实验新设计. University Chemistry, 2025, 40(8): 265-271. doi: 10.12461/PKU.DXHX202410061
7. [7]
  Qinwei Lu , Jinjie Lu , Juying Lei , Xubiao Luo , Yanbo Zhou . Cyclodextrin-boosted photocatalytic oxidation for efficient bisphenol A removal. Chinese Chemical Letters, 2025, 36(3): 110017-. doi: 10.1016/j.cclet.2024.110017
8. [8]
  Shuo Li , Qianfa Liu , Lijun Mao , Xin Zhang , Chunju Li , Da Ma . Benzothiadiazole-based water-soluble macrocycle: Synthesis, aggregation-induced emission and selective detection of spermine. Chinese Chemical Letters, 2024, 35(11): 109791-. doi: 10.1016/j.cclet.2024.109791
9. [9]
  Tong-Tong Zhou , Guan-Yu Ding , Xue Li , Li-Li Wen , Xiao-Xu Pang , Ying-Chen Duan , Ju-Yang He , Guo-Gang Shan , Zhong-Min Su . Design of near-infrared aggregation-induced emission photosensitizers by π-bridge engineering for boosting theranostic efficacy. Chinese Chemical Letters, 2025, 36(6): 110341-. doi: 10.1016/j.cclet.2024.110341
10. [10]
  Min Liu , Bin Feng , Feiyi Chu , Duoyang Fan , Fan Zheng , Fei Chen , Wenbin Zeng . An ESIPT-boosted NIR nanoprobe for ratiometric sensing of carbon monoxide via activatable aggregation-induced dual-color fluorescence. Chinese Chemical Letters, 2025, 36(5): 110043-. doi: 10.1016/j.cclet.2024.110043
11. [11]
  Zixi Zou , Jingyuan Wang , Yian Sun , Qian Wang , Da-Hui Qu . Controlling molecular assembly on time scale: Time-dependent multicolor fluorescence for information encryption. Chinese Chemical Letters, 2024, 35(7): 108972-. doi: 10.1016/j.cclet.2023.108972
12. [12]
  Yutong Xiong , Ting Meng , Wendi Luo , Bin Tu , Shuai Wang , Qingdao Zeng . Molecular conformational effects on co-assembly systems of low-symmetric carboxylic acids investigated by scanning tunneling microscopy. Chinese Journal of Structural Chemistry, 2025, 44(2): 100511-100511. doi: 10.1016/j.cjsc.2025.100511
13. [13]
  Zhu Shu , Xin Lei , Yeye Ai , Ke Shao , Jianliang Shen , Zhegang Huang , Yongguang Li . ATP-induced supramolecular assembly based on chromophoric organic molecules and metal complexes. Chinese Chemical Letters, 2024, 35(11): 109585-. doi: 10.1016/j.cclet.2024.109585
14. [14]
  Guoping Yang , Zhoufu Lin , Xize Zhang , Jiawei Cao , Xuejiao Chen , Yufeng Liu , Xiaoling Lin , Ke Li . Assembly of Y(Ⅲ)-containing antimonotungstates induced by malic acid with catalytic activity for the synthesis of imidazoles. Chinese Chemical Letters, 2024, 35(12): 110274-. doi: 10.1016/j.cclet.2024.110274
15. [15]
  Changlin Su , Wensheng Cai , Xueguang Shao . Water as a probe for the temperature-induced self-assembly transition of an amphiphilic copolymer. Chinese Chemical Letters, 2025, 36(4): 110095-. doi: 10.1016/j.cclet.2024.110095
16. [16]
  Kun Zhang , Xin-Yue Lou , Yan Wang , Weiwei Huan , Ying-Wei Yang . Emission enhancement induced by the supramolecular assembly of leggero pillar[5]arenes for the detection and separation of silver ions. Chinese Chemical Letters, 2025, 36(6): 110464-. doi: 10.1016/j.cclet.2024.110464
17. [17]
  Jun-Jie Fang , Zheng Liu , Yun-Peng Xie , Xing Lu . Superatomic Ag₅₈ nanoclusters incorporating a [MS₄@Ag₁₂]²⁺ (M = Mo or W) kernel show aggregation-induced emission. Chinese Chemical Letters, 2024, 35(10): 109345-. doi: 10.1016/j.cclet.2023.109345
18. [18]
  Xuejian Xing , Pan Zhu , E Pang , Shaojing Zhao , Yu Tang , Zheyu Hu , Quchang Ouyang , Minhuan Lan . D-A-D-structured boron-dipyrromethene with aggregation-induced enhanced phototherapeutic efficiency for near-infrared fluorescent and photoacoustic imaging-guided synergistic photodynamic and photothermal cancer therapy. Chinese Chemical Letters, 2024, 35(10): 109452-. doi: 10.1016/j.cclet.2023.109452
19. [19]
  Yunli Xu , Xuwen Da , Lei Wang , Yatong Peng , Wanpeng Zhou , Xiulian Liu , Yao Wu , Wentao Wang , Xuesong Wang , Qianxiong Zhou . Ru(Ⅱ)-based aggregation-induced emission (AIE) agents with efficient ¹O₂ generation, photo-catalytic NADH oxidation and anticancer activity. Chinese Chemical Letters, 2025, 36(5): 110168-. doi: 10.1016/j.cclet.2024.110168
20. [20]
  Wenjia Wang , Xingyue He , Xiaojie Wang , Tiantian Zhao , Osamu Muraoka , Genzoh Tanabe , Weijia Xie , Tianjiao Zhou , Lei Xing , Qingri Jin , Hulin Jiang . Glutathione-depleted cyclodextrin pseudo-polyrotaxane nanoparticles for anti-inflammatory oxaliplatin (Ⅳ) prodrug delivery and enhanced colorectal cancer therapy. Chinese Chemical Letters, 2024, 35(4): 108656-. doi: 10.1016/j.cclet.2023.108656

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(768)
HTML views(10)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142