Citation: Li-Hua Wang, Zhi-Jun Zhang, Heng-Yi Zhang, Hai-Lang Wu, Yu Liu. A twin-axial[5]pseudorotaxane based on cucurbit[8]uril and a-cyclodextrin[J]. Chinese Chemical Letters, ;2013, 24(11): 949-952.
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A twin-axial hetero[5]pseudorotaxane was constructed based on 1-hexyl-4,40-bipyridinium guest 1 and cucurbit[8]uril (CB[8]) and a-cyclodextrin (a-CD). In its structure, CB[8] included two bipyridinium units to realize the twin-axial mode, and the hexyl chain was threaded into the cavity of a-CD. The [5]pseudorotaxane contains two types of macrocyclic hosts while the single axial and twin axial modes co-exist in its structure. The transformation of [5]pseudorotaxane could be realized by the addition of acid and 2,6-dihydroxynaphthalene (HN).
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Keywords:
- Pseudorotaxane,
- Cucurbituril,
- Cyclodextrin,
- Self-assembly
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[1]
[1] (a) Z. Wang, D.S. Guo, J. Zhang, et al., Electro-responsive binary hydrogels based on calixarene and viologens, Acta Chim. Sin. 70 (2012) 1709-1715;
-
[2]
(b) 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;
-
[3]
(c) C. Yang, Recent progress in supramolecular chiral photochemistry, Chin. Chem. Lett. 24 (2013) 437-441;
-
[4]
(d) Z.J. Zhang, H. Wang, H.Y. Zhang, et al., Selectively fluorescent sensing behavior of phenylaza-15-crown-5-triazolyl coumarin for Hg2+ and Fe3+ in alcohol and aqueous media respectively, Chin. J. Chem. 31 (2013) 598-602.
-
[5]
[2] D.S. Guo, J. Zhang, Y. Liu, Calixarene-based supramolecular polymerization in solution, Chem. Soc. Rev. 41 (2012) 5907-5921.
-
[6]
[3] E.R. Kay, D.A. Leigh, F. Zerbetto, Synthetic molecular motors and mechanical machines, Angew. Chem. Int. Ed. 46 (2007) 72-191.
-
[7]
[4] D.H. Qu, H. Tian, Novel and efficient templates for assembly of rotaxanes and catenanes, Chem. Sci. 2 (2011) 1011-1015.
-
[8]
[5] (a) Z.J. Zhang, H.Y. Zhang, Y. Liu, Artificialmolecular devices and machines based on 24-crown-8 macrocyclic compound, Chem. J. Chin. Univ. 32 (2011) 1913-1927;
-
[9]
(b) H. Wang, Z.J. Zhang, H.Y. Zhang, et al., Synthesis of a bistable [3]rotaxane and its pH-controlled intramolecular charge-transfer behavior, Chin. Chem. Lett. 24 (2013) 563-567.
-
[10]
[6] (a) Y.L. Sun, Y.W. Yang, D.X. Chen, et al., Mechanized silica nanoparticles based on pillar[5]arenes for on-command cargo release, Small 9 (2013), http://dx.doi.org/10.1002/smll.201300445;
-
[11]
(b) Y.L. Sun, B.J. Yang, S.X.A. Zhang, et al., Cucurbit[7]uril pseudorotaxane-based photoresponsive supramolecular nanovalve, Chem. Eur. J. 18 (2012) 9212-9216;
-
[12]
(c) Y.W. Yang, Towards biocompatible nanovalves based on mesoporous silica nanoparticles, Med. Chem. Commun. 2 (2011) 1033-1049;
-
[13]
(d) H. Li, Y.W. Yang, Gold nanoparticles functionalized with supramolecular macrocycles, Chin. Chem. Lett. 24 (2013) 545-552;
-
[14]
(e) Y.L. Sun, Y.W. Yang, W. Wu, et al., Supramolecular nanovalve systems based on macrocyclic synthetic receptors, Chem. J. Chin. Univ. 33 (2012) 1635-1642;
-
[15]
(f) P. Liu, X.G. Shao, W.S. Cai, Application of pesudorotaxanes/rotaxanes in drug carriers, Prog. Chem. 25 (2013) 692-697.
-
[16]
[7] C. Li, X. Shu, J. Li, et al., Selective and effective binding of pillar[5,6]arenes toward secondary ammonium salts with a weakly coordinating counteranion, Org. Lett. 14 (2012) 4126-4129.
-
[17]
[8] Z.J. Zhang, H.Y. Zhang, H. Wang, et al., A twin-axial hetero[7]rotaxane, Angew. Chem. Int. Ed. 50 (2011) 10834-10838.
-
[18]
[9] Z.J. Zhang, Y. Liu, Construction and function of interpenetrated molecules based on the positively charged axle components, Synlett 23 (2012) 1733-1750.
-
[19]
[10] Y. Liu, X.Y. Li, H.Y. Zhang, et al., Cyclodextrin-driven movement of cucurbit[7]uril, J. Org. Chem. 72 (2007) 3640-3645.
-
[20]
[11] J. Lagona, P. Mukhopadhyay, S. Chakrabarti, et al., The cucurbit[n]uril family, Angew. Chem. Int. Ed. 44 (2005) 4844-4870.
-
[21]
[12] S. Andersson, D.P. Zou, R. Zhang, et al., Selective positioning of CB[8] on two linked viologens and electrochemically driven movement of the host compound, Eur. J. Org. Chem. (2009) 1163-1172.
-
[22]
[13] T. Ooya, D. Inoue, H.S. Choi, et al., pH-Responsive movement of cucurbit[7]uril in a diblock polypseudorotaxane containing dimethyl b-cyclodextrin and cucurbit[7]uril, Org. Lett. 8 (2006) 3159-3162.
-
[23]
[14] C. Yang, Y.H. Ko, N. Selvapalam, et al., Dynamic switching between single-and double-axial rotaxanes manipulated by charge and bulkiness of axle termini, Org. Lett. 9 (2007) 4789-4792.
-
[24]
[15] Z.J. Ding, H.Y. Zhang, L.H. Wang, et al., A heterowheel [3]pseudorotaxane by integrating b-cyclodextrin and cucurbit[8]uril inclusion complexes, Org. Lett. 13 (2011) 856-859.
-
[25]
[16] Y. Chen, Y. Liu, Cyclodextrin-based bioactive nanosupramolecules, Chem. Soc. Rev. 39 (2010) 495-505.
-
[26]
[17] Y.H. Ko, E. Kim, I. Hwang, Supramolecular assemblies built with host-stabilized charge-transfer interactions, Chem. Commun. (2007) 1305-1315.
-
[27]
[18] U. Rauwald, O.A. Scherman, Supramolecular block copolymers with cucurbit[8]uril in water, Angew. Chem. Int. Ed. 47 (2008) 3950-3953.
-
[28]
[19] S. Deroo, U. Rauwald, C.V. Robinson, et al., Discrete, multi-component complexes with cucurbit[8]uril in the gas-phase, Chem. Commun. (2009) 644-646.
-
[29]
[20] J.M. Zayed, F. Biedermann, U. Rauwald, et al., Probing cucurbit[8]uril-mediated supramolecular block copolymer assembly in water using diffusion NMR, Polym. Chem. 1 (2010) 1434-1436.
-
[30]
[21] R.J. Coulston, S.T. Jones, T.C. Lee, et al., Supramolecular gold nanoparticle-polymer composites formed in water with cucurbit[8]uril, Chem. Commun. 47 (2011) 164-166.
-
[31]
[22] F. Tian, N. Cheng, N. Nouvel, et al., Site-selective immobilization of colloids on Au substrates via a noncovalent supramolecular "handcuff", Langmuir 26 (2010) 5323-5328.
-
[32]
[23] E.A. Appel, F. Biedermann, U. Rauwald, et al., Supramolecular cross-Linked networks via host-guest complexation with cucurbit[8]uril, J. Am. Chem. Soc. 132 (2010) 14251-14260.
-
[33]
[24] F. Biedermann, U. Rauwald, J.M. Zayed, et al., A supramolecular route for reversible protein-polymer conjugation, Chem. Sci. 2 (2011) 279-286.
-
[34]
[25] M.F. Pepitone, G.G. Jernigan, J.S. Melinger, et al., Synthesis and characterization of donor-acceptor chromophores for unidirectional electron transfer, Org. Lett. 9 (2007) 801-804.
-
[35]
[26] Z.J. Zhang, Y.M. Zhang, Y. Liu, Controlled molecular self-assembly behaviors between cucurbituril and bispyridinium derivatives, J. Org. Chem. 76 (2011) 4682-4685.
-
[36]
[27] Z.J. Zhang, H.Y. Zhang, L. Chen, et al., Interconversion between [5]pseudorotaxane and pseudorotaxane by pasting/detaching two axle molecules, J. Org. Chem. 76 (2011) 8270-8276.
-
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