Citation: Hui Wang, Zhi-Jun Zhang, Heng-Yi Zhang, Yu Liu. Synthesis of a bistable [3]rotaxane and its pH-controlled intramolecular charge-transfer behavior[J]. Chinese Chemical Letters, ;2013, 24(07): 563-567. shu

Synthesis of a bistable [3]rotaxane and its pH-controlled intramolecular charge-transfer behavior

1.
Department of Chemistry, State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China

Corresponding author: Yu Liu,
Received Date: 26 February 2013
Available Online: 29 March 2013

A [3]rotaxane 1 involving two naphtho-21-crown-7 (N21C7) rings and a dumbbell-shaped component 4 was synthesized. The dumbbell-shape molecule 4 contains one viologen nucleus, two secondary alkyl ammonium sites and two phenyl stoppers. After threading the N21C7 ring with the thread-like ammonium guest 3, the copper(I)-catalyzed Huisgen alkyne-azide 1,3-dipolar cycloaddition (CuAAC "click" reaction), was performed to connect the pseudorotaxanes with viologen unit 2 and generate 1. Through treating the [3]rotaxane by the base and acid circularly, the two N21C7 rings can make shuttling motion along the axle. Meanwhile the distance between the electron-deficient viologen unit and the electron-rich naphthol group can be adjusted precisely along with a remarkable intramolecular chargetransfer (CT) behavior.
- Rotaxane,
- Crown ether,
- Charger transfer (CT),
- Click chemistry
1. [1]
  [1] (a) V. Balzani, A. Credi, M. Venturi, Molecular Devices and Machines-Concepts and Perspectives for the Nanoworld, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2008;
2. [2]
  (b) E.R. Kay, D.A. Leigh, F. Zerbetto, Synthetic molecular motors and mechanical machines, Angew. Chem. Int. Ed. 46 (2007) 72-191;
3. [3]
  (c) X. Ma, H. Tian, Bright functional rotaxanes, Chem. Soc. Rev. 39 (2010) 70-80;
4. [4]
  (d) C.J. Bruns, J.F. Stoddart, The mechanical bond: a work of art, Top. Curr. Chem. 323 (2012) 19-72.
5. [5]
  [2] S.Y. Hsueh, C.T. Kuo, T.W. Lu, et al., Acid/base-and anion-controllable organogels formed from a urea-based molecular switch, Angew. Chem. Int. Ed. 49 (2010) 9170-9173.
6. [6]
  [3] H. Yan, C. Teh, S. Sreejith, et al., Functional mesoporous silica nanoparticles for photothermal-controlled drug delivery in vivo, Angew. Chem. Int. Ed. 51 (2012) 8373-8377.
7. [7]
  [4] Y. Liu, A.H. Flood, P.A. Bonvallet, et al., Linear artificial molecular muscles, J. Am. Chem. Soc. 127 (2005) 9745-9759.
8. [8]
  [5] (a) Q. Jiang, H.Y. Zhang, M. Han, et al., pH-Controlled intramolecular chargetransfer behavior in bistable [3]rotaxane, Org. Lett. 12 (2010) 1728-1731;
9. [9]
  (b) Y. Jiang, J.B. Guo, C.F. Chen, A new [3]rotaxane molecular machine based on a dibenzylammonium ion and a triazolium station, Org. Lett. 12 (2010) 4248-4251;
10. [10]
  (c) Z.J. Zhang, H.Y. Zhang, Y. Liu, Artificial molecular devices and machines based on 24-crown-8 macrocyclic compound, Chem. J. Chin. Univ. 32 (2011) 1913-1927;
11. [11]
  (d) H. Zhang, J. Hu, D.H. Qu, Dual-mode control of PET process in a ferrocenefunctionalized[2]rotaxane with high-contrast fluorescence output, Org. Lett. 14 (2012) 2334-2337;
12. [12]
  (e) Z.J. Zhang, Y. Liu, Construction and function of interpenetrated molecules based on the positively charged axle components, Synlett 23 (2012) 1733-1750.
13. [13]
  [6] C. Zhang, S. Li, J. Zhang, et al., Benzo-21-crown-7/secondary dialkylammonium salt [2]pseudorotaxane-and [2]rotaxane-type threaded structures, Org. Lett. 9 (2007) 5553-5556.
14. [14]
  [7] (a) Z.J. Zhang, H.Y. Zhang, H. Wang, et al., A twin-axial hetero[7]rotaxane, Angew. Chem. Int. Ed. 50 (2011) 10834-10838;
15. [15]
  (b) W. Jiang, H.D.F. Winkler, C.A. Schalley, Integrative self-sorting: construction of a cascade-stoppered hetero[3]rotaxane, J. Am. Chem. Soc. 130 (2008) 13852-13853;
16. [16]
  (c) P.N. Chen, C.C. Lai, S.H. Chiu, Self-sorting under solvent-free conditions: one-pot synthesis of a hetero[3]rotaxane, Org. Lett. 13 (2011) 4660-4663.
17. [17]
  [8] A.C. Bissember, A. Levina, G.C. Fu, A mild, palladium-catalyzed method for the dehydrohalogenation of alkyl bromides: synthetic and mechanistic studies, J. Am. Chem. Soc. 134 (2012) 14232-14237.
18. [18]
  [9] F. Arico, J.D. Badjic, S.J. Cantrill, et al., Templated synthesis of interlocked molecules, Top. Curr. Chem. 249 (2005) 203-259.
19. [19]
  [10] W.R. Dichtel, O.S. Miljanic, J.M. Spruell, et al., Efficient templated synthesis of donor-acceptor rotaxanes using click chemistry, J. Am. Chem. Soc. 128 (2006) 10388-10390.
20. [20]
  [11] (a) O.Š. Miljanić, W.R. Dichtel, I. Aprahamian, et al., Rotaxanes and catenanes by click chemistry, QSAR Comb. Sci. 26 (2007) 1165-1174;
21. [21]
  (b) F. Coutrot, E. Busseron, A new glycorotaxane molecular machine based on an anilinium and a triazolium station, Chem. Eur. J. 14 (2008) 4784-4787;
22. [22]
  (c) K.D. Hanni, D.A. Leigh, The application of CuAAC click chemistry to catenane and rotaxane synthesis, Chem. Soc. Rev. 39 (2010) 1240-1251.
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沈阳化工大学材料科学与工程学院沈阳 110142