Citation: Wang Tian-Nan, Yang Guang, Wu Li-Bin, Chen Guo-Song. Self-assembly of supra-amphiphile of azobenzenegalactopyranoside based on dynamic covalent bond and its dual responses[J]. Chinese Chemical Letters, ;2016, 27(12): 1740-1744. doi: 10.1016/j.cclet.2016.05.009 shu

Self-assembly of supra-amphiphile of azobenzenegalactopyranoside based on dynamic covalent bond and its dual responses

The State Key Laboratory of Molecular Engineering of Polymers and Department of Macromolecular Science, Fudan University, Shanghai 200433, China

Corresponding author: Chen Guo-Song, guosong@fudan.edu.cn
Received Date: 7 April 2016
Revised Date: 3 May 2016
Accepted Date: 5 May 2016
Available Online: 21 December 2016

Figures(7)

In this paper, dynamic covalent bond has been employed to construct supra-amphiphile of carbohydrate for the first time. In neutral environment, the molecule was fabricated by reacting a hydrophobic building block bearing benzoic aldehyde with a hydrophilic building block bearing hydrazine to form a sugar-containing supra-amphiphile based on acylhydrazone bond. The obtained azobenzenegalactopyranoside (Azo-Gal) supra-amphiphile self-assembled to fibrillar structure in water, which showed dual responses to UV light and pH.
- Supra-amphiphile,
- Self-assembly,
- Dynamic covalent bond,
- Carbohydrate,
- Dual responses
1. [1]
  C Wang, Z.Q Wang, X Zhang. Amphiphilic building blocks for self-assembly:from amphiphiles to supra-amphiphiles[J]. Acc. Chem. Res, 2012,45:608-618. doi: 10.1021/ar200226d
2. [2]
  C.B Minkenberg, L Florusse, R Eelkema, G.J.M Koper, J.H van Esch. Triggered selfassembly of simple dynamic covalent Surfactants[J]. J. Am. Chem. Soc, 2009,131:11274-11275. doi: 10.1021/ja902808q
3. [3]
  G.T Wang, C Wang, Z.Q Wang, X Zhang. Bolaform superamphiphile based on a dynamic covalent bond and its self-assembly in water[J]. Langmuir, 2011,27:12375-12380. doi: 10.1021/la203040e
4. [4]
  P.Y Xing, T Sun, A.Y Hao. Vesicles from supramolecular amphiphiles[J]. RSC Adv, 2013,3:24776-24793. doi: 10.1039/c3ra44569k
5. [5]
  F Versluis, I Tomatsu, S Kehr. Shape and release control of a peptide decorated vesicle through pH sensitive orthogonal supramolecular interactions[J]. J. Am. Chem. Soc, 2009,131:13186-13187. doi: 10.1021/ja9026264
6. [6]
  Y.J Jeon, P.K Bharadwaj, S.W Choi, J.W Lee, K Kim. Supramolecular amphiphiles:spontaneous formation of vesicles triggered by formation of a charge-transfer complex in a host[J]. Angew. Chem. Int. Ed, 2002,414807.
7. [7]
  Q.Z Zhou, H.J Jiang, R Chen. A triply-responsive pillar[6] arene-based supramolecular amphiphile for tunable formation of vesicles and controlled release[J]. Chem. Commun, 2014,50:10658-10660. doi: 10.1039/C4CC05031B
8. [8]
  L Shao, J Zhou, B Hua, G.C Yu. A dual-responsive supra-amphiphile based on a water-soluble pillar[7] arene and a naphthalene diimide-containing guest[J]. Chem. Commun, 2015,51:7215-7218. doi: 10.1039/C5CC00937E
9. [9]
  C.R Bertozzi, L.L Kiessling. Chemical glycobiology[J]. Science, 2001,291:2357-2364. doi: 10.1126/science.1059820
10. [10]
  M Delbianco, P Bharate, S Varela-Aramburu, P.H Seeberger. Carbohydrates in supramolecular chemistry[J]. Chem. Rev, 2015,116:1693-1752.
11. [11]
  Y.T Kang, K Liu, X Zhang. Supra-amphiphiles:a new bridge between colloidal science and supramolecular chemistry[J]. Langmuir, 2014,30:5989-6001. doi: 10.1021/la500327s
12. [12]
  L.L Yang, H Yang, F Li, X Zhang. Supramolecular glycolipid based on hostenhanced charge transfer interaction[J]. Langmuir, 2013,29:12375-12379. doi: 10.1021/la402973g
13. [13]
  J.M Lehn. Dynamers:dynamic molecular and supramolecular polymers[J]. Prog. Polym. Sci, 2005,30:814-831. doi: 10.1016/j.progpolymsci.2005.06.002
14. [14]
  G.S Kumar, D.C Neckers. Photochemistry of azobenzene-containing polymers[J]. Chem. Rev, 1989,89:1915-1925. doi: 10.1021/cr00098a012
15. [15]
  M.L Rahman, G Hegde, S.M Sarkar, M.M Yusoff. Synthesis and photoswitching properties of azobenzene liquid crystals with a pentafluorobenzene terminal[J]. Chin. Chem. Lett, 2014,25:1611-1614. doi: 10.1016/j.cclet.2014.06.025
16. [16]
  J Wu, X.M Lu, F Shan, J.F Guan, Q.H Lu. Photoresponding ionic complex containing azobenzene chromophore for use in birefringent film[J]. Chin. Chem. Lett, 2014,25:15-18. doi: 10.1016/j.cclet.2013.11.008
17. [17]
  K.C Wei, J Li, J.H Liu, G.S Chen, M Jiang. Reversible vesicles of supramolecular hybrid nanoparticles[J]. Soft Matter, 2012,8:3300-3303. doi: 10.1039/c2sm25178g
18. [18]
  Z.Q Li, Y.M Zhang, H.Z Chen, J Zhao, Y Liu. Hierarchical organization of spherical assembly with reversibly photocontrollable cross-links[J]. J. Org. Chem, 2013,78:5110-5114. doi: 10.1021/jo400772j
19. [19]
  J Zhao, Y.M Zhang, H.L Sun, X.Y Chang, Y Liu. Multistimuli-responsive supramolecular assembly of cucurbituril/cyclodextrin pairs with an azobenzene-containing bispyridinium guest[J]. Chem. Eur. J, 2014,20:15108-15115. doi: 10.1002/chem.201404216
20. [20]
  Y Wang, N Ma, Z Wang, X Zhang. Photocontrolled reversible supramolecular assemblies of an azobenzene-containing surfactant with alpha-cyclodextrin[J]. Angew. Chem. Int. Ed, 2007,46:2823-2826. doi: 10.1002/(ISSN)1521-3773
21. [21]
  X.J Liao, G.S Chen, X.X Liu. Photoresponsive pseudopolyrotaxane hydrogels based on competition of host-guest interactions[J]. Angew. Chem. Int. Ed, 2010,49:4409-4413. doi: 10.1002/anie.201000141
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