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.
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沈阳化工大学材料科学与工程学院沈阳 110142