Citation: Yang Luo, Wei Zhang, Jie Zhao, Mao-Xia Yang, Qian Ren, Carl Redshaw, Zhu Tao, Xin Xiao. A novel pillar[5]arene-cucurbit[10]uril based host-guest complex: Synthesis, characterization and detection of paraquat[J]. Chinese Chemical Letters, ;2023, 34(3): 107780. doi: 10.1016/j.cclet.2022.107780 shu

A novel pillar[5]arene-cucurbit[10]uril based host-guest complex: Synthesis, characterization and detection of paraquat

Yang Luo ^a ,
Wei Zhang ^a ,
Jie Zhao ^a ,
Mao-Xia Yang ^a ,
Qian Ren ^a ,
Carl Redshaw ^b ,
Zhu Tao ^a ,
Xin Xiao ^{a, *,}

a.
Key Laboratory of Macrocyclic and Supramolecular Chemistry of Guizhou Province, Institute of Applied Chemistry, Guizhou University, Guiyang 550025, China
b.
Department of Chemistry, University of Hull, Hull HU6 7RX, United Kingdom

gyhxxiaoxin@163.com

Received Date: 26 May 2022
Revised Date: 19 August 2022
Accepted Date: 23 August 2022
Available Online: 25 August 2022

Figures(6)

The macrocyclic family comprising pillar[n]arenes and cucurbit[n]urils have received much attention recently. However, studies on the construction of supramolecular complexes formed directly with derivatized pillar[n]arenes and cucurbit[n]urils are scant. Given the interest in such systems, herein we have synthesized a new type of naphthalene-derivatized pillar[n]arene NTP5 and selected Q[10] as the host molecule. The 4-[2-(1-naphthalenyl)ethenyl]pyridine of NTP5 is encapsulated by Q[10] and formed a host-guest complex in water-acetic acid (1:1) solution accompanied by enhanced fluorescence, which changed the morphology of NTP5 from a sphere to a porous form. In addition, the fluorescence of Q[10]-NTP5 can be quenched by the addition of the highly toxic pesticide paraquat (PQ), and the mechanism was shown to be the formation of a new charge transfer ternary system of Q[10]-NTP5-PQ. This work provides new ideas for the contribution of supramolecular assemblies based on derivatized pillar[n]arenes and their combination with cucurbit[n]urils and reveals their potential applications.
- Pillar[n]arene,
- Cucurbit[n]uril,
- Paraquat,
- Supramolecular assembly,
- Detection
1. [1]
  T. Ogoshi, S. Kanai, S. Fujinami, T. Yamagishi, Y. Nakamoto, J. Am. Chem. Soc.130 (2008) 5022–5023. doi: 10.1021/ja711260m
2. [2]
  M. Xue, Y. Yang, X. Chi, Z. Zhang, F. Huang, Acc. Chem. Res. 45 (2012) 1294–1308. doi: 10.1021/ar2003418
3. [3]
  P.J. Cragg, K. Sharma, Chem. Soc. Rev. 41 (2012) 597–607. doi: 10.1039/C1CS15164A
4. [4]
  E. Lee, H. Ju, I.H. Park, et al., J. Am. Chem. Soc. 140 (2018) 9669–9677. doi: 10.1021/jacs.8b05751
5. [5]
  J.F. Chen, X. Yin, B. Wang, et al., Angew. Chem. Int. Ed. 59 (2020) 11267–11272. doi: 10.1002/anie.202001145
6. [6]
  A.J. Savyasachi, O. Kotova, S. Shanmugaraju, et al., Chem 3 (2017) 764–811. doi: 10.1016/j.chempr.2017.10.006
7. [7]
  J.R. Wu, Y.W. Yang, Angew. Chem. Int. Ed. 60 (2021) 1690–1701. doi: 10.1002/anie.202006999
8. [8]
  Y. Cao, Y. Chen, Z. Zhang, et al., Chin. Chem. Lett. 32 (2021) 349–352. doi: 10.1016/j.cclet.2020.03.058
9. [9]
  J. Wang, M. Cen, J. Wang, et al., Chin. Chem. Lett. 33 (2022) 1475–1478. doi: 10.3390/sym14071475
10. [10]
  B. Lu, Z. Zhang, Y. Ji, et al., Sci. China Chem. 65 (2022) 1134–1141. doi: 10.1007/s11426-022-1232-9
11. [11]
  L. Xia, J. Wu, B. Huang, et al., Chem. Commun. 56 (2020) 11134–11137. doi: 10.1039/d0cc03574b
12. [12]
  L. Xia, J. Tian, T. Yue, et al., Adv. Healthcare Mater. 11 (2022) 2102015. doi: 10.1002/adhm.202102015
13. [13]
  J. Yang, L. Shao, J. Yuan, F. Huang, Chem. Commun. 52 (2016) 12510–12512. doi: 10.1039/C6CC07433B
14. [14]
  C. Ke, N.L. Strutt, H. Li, et al., J. Am. Chem. Soc. 135 (2013) 17019–30. doi: 10.1021/ja407229h
15. [15]
  T. Ogoshi, R. Shiga, T. Yamagishi, J. Am. Chem. Soc. 134 (2012) 4577–4580. doi: 10.1021/ja300989n
16. [16]
  D. Zhang, H. Tang, G. Zhang, L. Wang, D. Cao, Chem. Commun. 57 (2021) 6562–6565. doi: 10.1039/d1cc01777b
17. [17]
  T. Zhang, Y. Liu, B. Hu, et al., Chin. Chem. Lett. 30 (2019) 949–952. doi: 10.1016/j.cclet.2018.12.029
18. [18]
  Y. Yang, X.L. Ni, J.F. Xu, X. Zhang, Chem. Commun. 55 (2019) 13836–13839. doi: 10.1039/c9cc07127j
19. [19]
  M. Cao, F. Hu, X. Han, et al., Chin. J. Chem. 33 (2015) 351–355. doi: 10.1002/cjoc.201400881
20. [20]
  Y. Luo, S. Gan, W. Zhang, et al., Mater. Chem. Front. 6 (2022) 1021–1025. doi: 10.1039/d2qm00084a
21. [21]
  W.T. Xu, Y. Luo, W.W. Zhao, et al., J. Agric. Food Chem. 69 (2021) 584–591. doi: 10.1021/acs.jafc.0c05577
22. [22]
  F. Liu, S. Chowdhury, R. Rosas, et al., Org. Lett. 23 (2021) 5283–5287. doi: 10.1021/acs.orglett.1c00773
23. [23]
  G. Fan, X. Yu, X. Han, Z. Zhao, S. Liu, Org. Lett. 23 (2021) 6633–6637. doi: 10.1021/acs.orglett.1c02081
24. [24]
  H. Wang, Y. Yang, B. Yuan, et al., ACS Appl. Mater. Interfaces 13 (2021) 2269–2276. doi: 10.1021/acsami.0c18725
25. [25]
  E.T. Luis, A.I. Day, B. König, J.E. Beves, Inorg. Chem. 59 (2020) 9135–9142. doi: 10.1021/acs.inorgchem.0c00986
26. [26]
  O. Danylyuk, V. Sashuk, CrystEngComm 22 (2020) 2900–2903. doi: 10.1039/d0ce00296h
27. [27]
  H.J. Kim, J. Heo, W.S. Jeon, et al., Angew. Chem. Int. Ed. 40 (2001) 1526–1529. doi: 10.1002/1521-3773(20010417)40:8<1526::AID-ANIE1526>3.0.CO;2-T
28. [28]
  W. Gong, X. Yang, P.Y. Zavalij, et al., Chem. Eur. J. 22 (2016) 17612–17618. doi: 10.1002/chem.201604149
29. [29]
  X. Yang, R. Wang, A. Kermagoret, D. Bardelang, Angew. Chem. Int. Ed. 59 (2020) 21280–21292. doi: 10.1002/anie.202004622
30. [30]
  G. Wu, Z. Huang, O.A. Scherman, Angew. Chem. Int. Ed. 59 (2020) 15963–15967. doi: 10.1002/anie.202006530
31. [31]
  K.M. Anis-Ul-Haque, C.E. Woodward, A.I. Day, L. Wallace, Inorg. Chem. 59 (2020) 3942–3953. doi: 10.1021/acs.inorgchem.9b03603
32. [32]
  M. Liu, L. Chen, P. Shan, et al., ACS Appl. Mater. Inter. 13 (2021) 7434–7442. doi: 10.1021/acsami.0c20292
33. [33]
  Y. Luo, W. Zhang, M. Liu, et al., Chin. Chem. Lett. 32 (2021) 367–370. doi: 10.1016/j.cclet.2020.02.023
34. [34]
  Y. Zhang, K. Lu, M. Liu, et al., Dalton Trans. 49 (2020) 404–410. doi: 10.1039/c9dt04299g
35. [35]
  X. Yang, F. Liu, Z. Zhao, et al., Chin. Chem. Lett. 29 (2018) 1560–1566. doi: 10.1016/j.cclet.2018.01.032
36. [36]
  J. Chen, Y. Su, F. Lin, et al., Ecotoxicol. Environ. Saf. 224 (2021) 112711. doi: 10.1016/j.ecoenv.2021.112711
37. [37]
  B. Parmar, K.K. Bisht, Y. Rachuri, E. Suresh, Inorg. Chem. Front. 7 (2020) 1082–1107. doi: 10.1039/c9qi01549c
38. [38]
  M. Zhang, X. Yan, F. Huang, Z. Niu, H.W. Gibson, Acc. Chem. Res. 47 (2014) 1995–2005. doi: 10.1021/ar500046r
39. [39]
  J.F. Chen, G. Meng, Q. Zhu, S. Zhang, P. Chen, J. Mater. Chem. C 7 (2019) 11747–11751. doi: 10.1039/c9tc03831k
40. [40]
  M. Noboru, K. Yozo, K. Masao, Bull. Chem. Soc. Jpn. 29 (1956) 465–470. doi: 10.1246/bcsj.29.465
41. [41]
  K. Li, Y. Liu, Y. Li, et al., Chem. Sci. 8 (2017) 7258–7267. doi: 10.1039/C7SC03076B
42. [42]
  H. Sun, X.X. Tang, B.X. Miao, Y. Yang, Z. Ni, Sens. Actuat. B: Chem. 267 (2018) 448–456. doi: 10.1016/j.snb.2018.04.022
43. [43]
  L. Yang, H. Yang, F. Li, X. Zhang, Langmuir 29 (2013) 12375–12379. doi: 10.1021/la402973g
44. [44]
  Y. Jiao, J.F. Xu, Z. Wang, X. Zhang, ACS Appl. Mater. Interfaces 9 (2017) 22635–22640. doi: 10.1021/acsami.7b07026
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