Citation: Liu Ran, Zhang Yuxue, Wu Wanhua, Liang Wenting, Huang Qinfei, Yu Xingke, Xu Wei, Zhou Dayang, Selvapalam Narayanan, Yang Cheng. Temperature-driven braking of γ-cyclodextrin-curcubit[6]uril-cowheeled [4]rotaxanes[J]. Chinese Chemical Letters, ;2019, 30(3): 577-581. doi: 10.1016/j.cclet.2018.12.002 shu

Temperature-driven braking of γ-cyclodextrin-curcubit[6]uril-cowheeled [4]rotaxanes

a.
Key Laboratory of Green Chemistry & Technology, College of Chemistry, State Key Laboratory of Biotherapy, West China Medical Center, and Healthy Food Evaluation Research Center, Sichuan University, Chengdu 610064, China
b.
Institute of Environmental Sciences, Department of Chemistry, Shanxi University, Taiyuan 030006, China
c.
Comprehensive Analysis Center, ISIR, Osaka University, Mihogaoka, Ibaraki 567-0047, Japan
d.
Center for Supramolecular Chemistry, International Research Center and Department of Chemistry, Kalasalingam University, Krishnankoil, Tamil Nadu 626126, India

yangchengyc@scu.edu.cn

Received Date: 8 October 2018
Revised Date: 7 November 2018
Accepted Date: 3 December 2018
Available Online: 7 March 2018

Figures(7)

Several cyclodextrin-cucurbit[6]uril-cowheeled [4]rotaxanes were synthesized through the cucurbit[6] uril-templated azide-alkyne 1, 3-dipolar cycloaddition. The intramolecular interaction between the aromatic axle and the capping groups of cyclodextrin moieties was investigated by UV-vis, fluorescence, circular dichroism and NMR spectroscopic studies. The rotational kinetic of the wheel around the axle can be manipulated by adjusting the temperature. The capping group apparently slowed down the rotation of the wheel, playing a role of the brake, and lowering the temperature can stop the rotation of the wheel on the NMR timescale.
- Temperature-control,
- Rotational kinetics,
- Rotaxane,
- Cyclodextrin,
- Cucurbit[6]uril
1. [1]
  (a) V. Balzani, A. Credi, F.M. Raymo, J.F. Stoddart, Angew. Chem. Int. Ed. 39 (2000) 3348-3391;
  (b) J.P. Sauvage, C. Dietrich-Buchecker, Molecular Catenanes, Rotaxanes and Knots: A Journey Through the World of Molecular Topology, John Wiley & Sons, Weinheim, 1999.
2. [2]
  (a) N. Koumura, R.W. Zijlstra, R.A. Delden, et al., Nature 401 (1999) 152-155;
  (b) J. Conyard, A. Cnossen, W.R. Browne, et al., J. Am. Chem. Soc. 136 (2014) 9692-9700;
  (c) J.P. Collin, F. Durola, P. Mobian, et al., Eur. J. Inorg. Chem. (2007) 2420-2425.
3. [3]
  (a) E. Busseron, C. Romuald, F. Coutrot, Chem.-Eur. J. 16 (2010) 10062-10073;
  (b) T.R. Kelly, Acc. Chem. Res. 34 (2001) 514-522;
  (c) L.E. Harrington, L.S. Cahill, M.J. McGlinchey, Organometallics 23 (2004) 2884-2891;
  (d) D. Zhang, Q. Zhang, J.H. Su, et al., Chem. Commun. (2009) 1700-1702;
  (e) A. Faulkner, T.V. Leeuwen, B.L. Feringa, et al., J. Am. Chem. Soc. 138 (2016) 1359-1360;
  (f) W. Wu, S. Song, X. Cui, et al., Chin. Chem. Lett. 29 (2018) 95-98;
  (g) J. Yao, W. Wu, W. Liang, et al., Angew. Chem. Int. Ed. 56 (2017) 6869-6873.
4. [4]
  (a) Y. Wang, X. Qiao, W. Li, et al., Anal. Chim. Acta 650 (2009) 124-130;
  (b) W. Liang, C. Yang, M. Nishijima, et al., Beilstein J. Org. Chem. 8 (2012) 1305;
  (c) C. Yang, Q. Wang, M. Yamauchi, et al., Photochem. Photobiol. Sci. 13 (2014) 190-198;
  (d) X. Wei, W. Liang, W. Wu, et al., Org. Biomol. Chem. 13 (2015) 2905-2912;
  (e) J. Yi, W. Liang, X. Wei, et al., Chin. Chem. Lett. 29 (2018) 87-90.
5. [5]
  (a) Q. Wang, C. Yang, G. Fukuhara, et al., Beilstein J. Org. Chem. 7 (2011) 290;
  (b) C. Yang, C. Ke, F. Kahee, et al., Aust. J. Chem. 61 (2008) 565-568;
  (c) C. Yang, T. Mori, Y. Inoue, J. Org. Chem. 73 (2008) 5786-5794;
  (d) C. Yang, A. Nakamura, T. Wada, Y. Inoue, Org. Lett. 8 (2006) 3005-3008;
  (e) D.Q. Yuan, N. Kishikawa, C. Yang, et al., Chem. Commun. (2003) 416-417;
  (f) C. Yang, T. Mori, Y. Inoue, J. Org. Chem. 73 (2008) 5786-5794.
6. [6]
  (a) C. Yang, Chin. Chem. Lett. 24 (2013) 437-441;
  (b) Q. Huang, L. Jiang, W. Liang, et al., J. Org. Chem. 81 (2016) 3430-3434;
  (c) Q. Wang, C. Yang, C. Ke, et al., Chem. Commun. 47 (2011) 6849-6851;
  (d) X. Wei, W. Wu, R. Matsushita, et al., J. Am. Chem. Soc. 140 (2018) 3959-3974;
  (e) C. Yang, Y. Inoue, Chem. Soc. Rev. 43 (2014) 4123-4143;
  (f) J. Yao, Z. Yan, J. Ji, et al., J. Am. Chem. Soc. 136 (2014) 6916-6919;
  (g) J.C. Gui, Z.Q. Yan, Y. Peng, et al., Chin. Chem. Lett. 27 (2016) 1017-1021;
  (h) C. Yang, T. Mori, T. Wada, Y. Inoue, New J. Chem. 31 (2007) 697-702;
  (i) R. Lu, C. Yang, Y. Cao, et al., Chem. Commun. (2008) 374-376;
  (j) C. Yang, M. Nishijima, A. Nakamura, et al., Tetrahedron Lett. 48 (2007) 4357-4360.
7. [7]
  (a) C. Yang, H.K. Young, N. Selvapalam, et al., Org. Lett. 9 (2007) 4789-4792;
  (b) Z. Yan, Q. Huang, W. Liang, et al., Org. Lett. 19 (2017) 898-901;
  (c) L. Dai, W. Wu, W. Liang, et al., Chem. Commun. 54 (2018) 2643-2646.
8. [8]
  (a) S.Y. Jon, N. Selvapalam, D.H. Oh, et al., J. Am. Chem. Soc. 125 (2003) 10186-10187;
  (b) C. Yang, G. Fukuhara, A. Nakamura, et al., J. Photochem. Photobio. A: Chem. 173 (2005) 375-383;
  (c) C. Yang, A. Nakamura, T. Wada, Y. Inoue, Org. Lett. 8 (2006) 3005-3008.
9. [9]
  C. Ke, R.A. Smaldone, T. Kikuchi, H. Li, Angew. Chem. Int. Ed. 52(2013) 381-387. doi: 10.1002/anie.201205087
10. [10]
  M. Kajtár, C. Horváth-Toró, É. Kuthi, J. Szejtli, Proceedings of the First International Symposium on Cyclodextrins, Springer, 1982, pp. 181-193.
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