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RESEARCH ARTICLE
Contents Vol 73(7)

The Host–Guest Properties Observed Between the Viologens and Cyclopentanocucurbit[6]uril

Si-Yuan Cheng A , Yun-Xia Qu A , Zhu Tao A , Kai-Zhi Zhou A , Lian-Tong Wei B , Cong Wang A , Wei-Wei Zhao A , Dao-Fa Jiang A and Pei-Hua Ma https://orcid.org/0000-0002-0572-9461 A C
+ Author Affiliations
- Author Affiliations

A Key Laboratory of Macrocyclic and Supramolecular Chemistry of Guizhou Province, Guizhou University, Guiyang 550025, China.

B Guiyang Bewg Water Co. Ltd, Guiyang 550001, China.

C Corresponding author. Email: phma@gzu.edu.cn

Australian Journal of Chemistry 73(7) 601-607 https://doi.org/10.1071/CH19400
Submitted: 16 August 2019  Accepted: 25 November 2019   Published: 8 January 2020

Abstract

The interactions between cyclopentanocucurbit[6]uril (abbreviated as CyP6Q[6]) and a series of dialkyl-4,4′-bipyridinium and diaryl-4,4′-bipyridinium dicationic guest molecules, where the alkyl group is CH3(CH2)n with n = 0–6 (expressed as G1 to G7) and the aryl group is phenylene (G8) and xylene (G9), have been investigated in aqueous solution using 1H NMR spectroscopy, isothermal titration calorimetry (ITC), and electronic absorption spectroscopy. Our results show that G1 and G2 form 1 : 1 host–guest inclusion complexes with CyP6Q[6], in which the bipyridinium core is partially embedded in the cavity of CyP6Q[6]. G3–G9 form 2 : 1 dumbbell-type host–guest inclusion complexes, in which the substituents are encapsulated by CyP6Q[6]. At the same time, CyP6Q[6] was compared with several other cucurbit[n]urils (Q[n]s) and their derivatives, such as Q[6], Q[7], and TMeQ[6], which have been reported to interact with this type of guest molecule. In its binding mode, CyP6Q[6] shows many interesting and different properties, and this difference was mainly reflected with G1 and G2.


References

[1]  A. Flinn, G. C. Hough, J. F. Stoddart, D. J. Williams, Angew. Chem. Int. Ed. Engl. 1992, 31, 1475.
         | Crossref | GoogleScholarGoogle Scholar |

[2]  H. Isobe, S. Sato, E. Nakamura, Org. Lett. 2002, 4, 1287.
         | Crossref | GoogleScholarGoogle Scholar | 11950344PubMed |

[3]  J. Z. Zhao, H. J. Kim, J. Oh, S. Y. Kim, J. W. Lee, S. Sakamoto, K. Yamaguchi, K. Kim, Angew. Chem. Int. Ed. 2001, 40, 4233.
         | Crossref | GoogleScholarGoogle Scholar |

[4]  S. Y. Jon, N. Selvapalam, D. H. Oh, J. K. Kang, S. Y. Kim, Y. J. Jeon, J. W. Lee, K. Kim, J. Am. Chem. Soc. 2003, 125, 10186.
         | Crossref | GoogleScholarGoogle Scholar | 12926937PubMed |

[5]  S. Huang, M. Yang, X. Y. Deng, Q. J. Zhu, Y. Huang, Z. Tao, K. Chen, Aust. J. Chem. 2019, 72, 533.
         | Crossref | GoogleScholarGoogle Scholar |

[6]  F. Wu, L. H. Wu, X. Xiao, Y. Q. Zhang, S. F. Xue, Z. Tao, A. I. Day, J. Org. Chem. 2012, 77, 606.
         | Crossref | GoogleScholarGoogle Scholar | 22121978PubMed |

[7]  L. H. Wu, X. L. Ni, F. Wu, Y. Q. Zhang, Q. J. Zhu, S. F. Xue, Z. Tao, J. Mol. Struct. 2009, 920, 183.
         | Crossref | GoogleScholarGoogle Scholar |

[8]  Y. X. Qu, Y. Q. Zhang, K. Z. Zhou, L. T. Wei, L. L. Zhan, S. Y. Cheng, Z. Tao, P. H. Ma, ChemistrySelect 2017, 2, 4360.
         | Crossref | GoogleScholarGoogle Scholar |

[9]  Y. X. Qu, K. Z. Zhou, K. Chen, Y. Q. Zhang, X. Xiao, Q. D. Zhou, Z. Tao, P. H. Ma, G. Wei, Inorg. Chem. 2018, 57, 7412.
         | Crossref | GoogleScholarGoogle Scholar | 29863854PubMed |

[10]  Y. X. Qu, R. L. Lin, Y. Q. Zhang, K. Z. Zhou, Q. D. Zhou, Q. J. Zhu, Z. Tao, P. H. Ma, J. X. Liu, G. Wei, Org. Chem. Front. 2017, 4, 1799.
         | Crossref | GoogleScholarGoogle Scholar |

[11]  W. J. Wu, F. Wu, A. I. Day, J. Org. Chem. 2017, 82, 5507.
         | Crossref | GoogleScholarGoogle Scholar | 28486806PubMed |

[12]  V. Kolman, M. S. A. Khan, M. Babinsky, R. Marek, V. Sindelar, Org. Lett. 2011, 13, 6148.
         | Crossref | GoogleScholarGoogle Scholar | 22066799PubMed |

[13]  M. S. A. Khan, D. Heger, M. Necas, V. Sindelar, J. Phys. Chem. B 2009, 113, 11054.
         | Crossref | GoogleScholarGoogle Scholar |

[14]  X. Xiao, Q. H. Hu, Z. Tao, Y. Q. Zhang, S. F. Xue, Q. J. Zhu, G. Wei, Chem. Phys. Lett. 2011, 514, 317.
         | Crossref | GoogleScholarGoogle Scholar |

[15]  X. Xiao, R. L. Lin, L. M. Zheng, W. Q. Sun, Z. Tao, S. F. Xue, Q. J. Zhu, J. X. Liu, RSC Adv. 2014, 4, 53665.
         | Crossref | GoogleScholarGoogle Scholar |

[16]  W. Ong, A. E. Kaifer, Angew. Chem. Int. Ed. 2003, 42, 2164.
         | Crossref | GoogleScholarGoogle Scholar |

[17]  W. Ong, A. E. Kaifer, J. Org. Chem. 2004, 69, 1383.
         | Crossref | GoogleScholarGoogle Scholar | 14961699PubMed |

[18]  H. J. Kim, W. S. Jeon, Y. H. Ko, K. Kim, Proc. Natl. Acad. Sci. USA 2002, 99, 5007.
         | Crossref | GoogleScholarGoogle Scholar | 11917115PubMed |

[19]  W. Ong, M. G. Kaifer, A. E. Kaifer, Org. Lett. 2002, 4, 1791.
         | Crossref | GoogleScholarGoogle Scholar | 12000300PubMed |

[20]  L. Mu, Study on Structure and Properties of Self-Assembly Systems Involving Cucurbit[n]urils with Some Medicament Molecules 2007, Ph.D. thesis, Guizhou University.

[21]  L. Mu, S. F. Xue, Y. Du, Y. J. Zhao, Q. J. Zhu, Z. Tao, Chem. J. Chin. Univ. 2006, 27, 654.

[22]  Y. J. Jeon, P. K. Bharadwaj, S. W. Choi, J. W. Lee, K. Kim, Angew. Chem. Int. Ed. 2002, 41, 4474.
         | Crossref | GoogleScholarGoogle Scholar |

[23]  J. B. Wittenberg, P. Y. Zavalij, L. Isaacs, Angew. Chem. Int. Ed. 2013, 52, 3690.
         | Crossref | GoogleScholarGoogle Scholar |

[24]  Z. Z. Gao, D. Bai, L. X. Chen, Z. Tao, X. Xiao, T. J. Prior, C. Redshaw, RSC Adv. 2017, 7, 461.
         | Crossref | GoogleScholarGoogle Scholar |

[25]  R. L. Lin, J. Q. Li, J. X. Liu, A. E. Kaifer, J. Org. Chem. 2015, 80, 10505.
         | Crossref | GoogleScholarGoogle Scholar | 26452148PubMed |

[26]  Q. Liu, Q. Li, X. J. Cheng, Y. Y. Xi, B. Xiao, X. Xiao, Q. Tang, Y. Huang, Z. Tao, S. F. Xue, Q. J. Zhu, J. X. Zhang, Chem. Commun. 2015, 51, 9999.
         | Crossref | GoogleScholarGoogle Scholar |

[27]  B. J. Cheng, A. E. Kaifer, Langmuir 2015, 31, 2997.
         | Crossref | GoogleScholarGoogle Scholar |

[28]  J. Lagona, P. Mukhopadhyay, S. Chakrabarti, L. Isaacs, Angew. Chem. Int. Ed. 2005, 44, 4844.
         | Crossref | GoogleScholarGoogle Scholar |

[29]  X. L. Ni, X. Xiao, H. Cong, L. L. Liang, K. Cheng, X. J. Cheng, N. N. Ji, Q. J. Zhu, S. F. Xue, Z. Tao, Chem. Soc. Rev. 2013, 42, 9480.
         | Crossref | GoogleScholarGoogle Scholar | 24048328PubMed |

[30]  K. I. Assaf, W. M. Nau, Chem. Soc. Rev. 2015, 44, 394.
         | Crossref | GoogleScholarGoogle Scholar | 25317670PubMed |

[31]  W. A. Freeman, W. L. Mock, N. Y. Shih, J. Am. Chem. Soc. 1981, 103, 7367.
         | Crossref | GoogleScholarGoogle Scholar |