Citation: Ting-Ting Huang, Jin-Fa Chen, Juan Liu, Tai-Bao Wei, Hong Yao, Bingbing Shi, Qi Lin. A novel fused bi-macrocyclic host for sensitive detection of Cr₂O₇²⁻ based on enrichment effect[J]. Chinese Chemical Letters, ;2024, 35(7): 109281. doi: 10.1016/j.cclet.2023.109281 shu

A novel fused bi-macrocyclic host for sensitive detection of Cr₂O₇²⁻ based on enrichment effect

Ting-Ting Huang ^a ,
Jin-Fa Chen ^a ,
Juan Liu ^b ,
Tai-Bao Wei ^a ,
Hong Yao ^a ,
Bingbing Shi ^a ,
Qi Lin ^{a, *,}

a.
Key Laboratory of Eco-functional Polymer Materials of the Ministry of Education, Key Laboratory of Eco-environmental Polymer Materials of Gansu Province, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070, China
b.
Key Laboratory of Environment-Friendly Composite Materials of the State Ethnic Affairs Commission, Gansu Provincial Biomass Function Composites Engineering Research Center, College of Chemical Engineering, Northwest Minzu University (Northwest University for Nationalities), Lanzhou 730000, China

linqi2004@126.com

Received Date: 4 August 2023
Revised Date: 27 October 2023
Accepted Date: 6 November 2023
Available Online: 9 November 2023

Figures(5)

Improving the highly selective and sensitive binding of chemosensor to target guest is always very challenging. In order to solve this issue, herein, the enrichment effect was introduced into the design of chemosensor molecule. A novel bi-fused-macrocyclic host molecule BPN1 was synthesized by bridging a pillar[5]arene and a naphthalene diimide (NDI) group through hydrogen-bond-rich chain. In the BPN1, the naphthalimide side ring is outside the cavity of the pillar[5]arene. In addition, Cr(Ⅵ) greatly threat human health and the environment due to its severe toxicity, and it is very important to develop effective chemosensor for sensitive and selective detection of Cr₂O₇²⁻ or its ion pairs. In this paper, the novel bi-fused-macrocyclic host molecule BPN1 can recognize Cr₂O₇²⁻ with high selectivity and sensitivity. The mechanism of BPN1 recognition of Cr₂O₇²⁻ was studied through experiments and density functional theory (DFT), the results show that BPN1 could supply enrichment effect to bind Cr₂O₇²⁻ through multiple weak interactions such as hydrogen bonds and anion-π, and achieve highly sensitive and selective detection of Cr₂O₇²⁻. It is a significant and feasible strategy for improve high selectivity and sensitivity of host to specific objects by using the enrichment effect of fused bi-macrocyclic.
- Pillar[5]arene,
- Bi-macrocyclic,
- Detection of Cr₂O₇²⁻,
- DFT,
- The enrichment effect
1. [1]
  J. Tian, X. Hu, Z. Hu, Nat. Commun. 13 (2022) 4293-4205. doi: 10.1038/s41467-022-31986-x
2. [2]
  R. Cen, M. Liu, J. He, et al., Chin. Chem. Lett. 34 (2023) 108195–108200. doi: 10.1016/j.cclet.2023.108195
3. [3]
  S. Sevim, A. Sorrenti, C. Franco, et al., Chem. Soc. Rev. 47 (2018) 3788–3803. doi: 10.1039/c8cs00025e
4. [4]
  Y. Meng, Y. Liu, Z. Wan, et al., Chem. Eng. J. 453 (2023) 139967–139975. doi: 10.1016/j.cej.2022.139967
5. [5]
  Q. Liang, B. Shao, S. Tong, et al., Chem. Eng. J. 405 (2021) 126951–126976. doi: 10.1016/j.cej.2020.126951
6. [6]
  Y. Jia, J. Li, Acc. Chem. Res. 52 (2019) 1623–1631. doi: 10.1021/acs.accounts.9b00015
7. [7]
  C. Tu, W. Wu, W. Liang, et al., Angew. Chem. Int. Ed. 61 (2022) e202203541. doi: 10.1002/anie.202203541
8. [8]
  B. Li, Q. Xu, X. Shen, et al., Chin. Chem. Lett. 34 (2023) 108015. doi: 10.1016/j.cclet.2022.108015
9. [9]
  R. Kumar, A. Sharma, H. Singh, et al., Chem. Rev. 119 (2019) 9657–9721. doi: 10.1021/acs.chemrev.8b00605
10. [10]
  X. Zhang, S. Tong, J. Zhu, et al., Chem. Sci. 14 (2023) 827–832. doi: 10.1039/d2sc06234h
11. [11]
  P. Li, Y. Chen, Y. Liu, Chin. Chem. Lett. 30 (2019) 1190–1197. doi: 10.1016/j.cclet.2019.03.035
12. [12]
  H. Nie, Z. Wei, X.L. Ni, et al., Chem. Rev. 122 (2022) 9032–9077. doi: 10.1021/acs.chemrev.1c01050
13. [13]
  H. Liang, Y. Yang, L. Shao, et al., J. Am. Chem. Soc. 145 (2023) 2870–2876. doi: 10.1021/jacs.2c10674
14. [14]
  H. Liang, B. Hua, F. Xu, et al., J. Am. Chem. Soc. 142 (2020) 19772–19778. doi: 10.1021/jacs.0c10570
15. [15]
  Y. Li, X. Lou, C. Wang, et al., Chin. Chem. Lett. 2023, 34, 107877. doi: 10.1016/j.cclet.2022.107877
16. [16]
  Y.J. Li, T.T. Huang, J. Liu, et al., ACS Sustainable Chem. Eng. 10 (2022) 7907–7915. doi: 10.1021/acssuschemeng.2c00537
17. [17]
  M. Li, Y. Liu, L. Shao, et al., J. Am. Chem. Soc. 145 (2023) 667–675. doi: 10.1021/jacs.2c11618
18. [18]
  K. Wang, M. Zuo, T. Zhang, et al., Chin. Chem. Lett. 34 (2023) 107848. doi: 10.1016/j.cclet.2022.107848
19. [19]
  B. Jiang, W. Wang, Y. Zhang, et al., Angew. Chem. Int. Ed. 56 (2017) 14438–14442. doi: 10.1002/anie.201707209
20. [20]
  J.R. Wu, G. Wu, D. Li, et al., Angew. Chem. Int. Ed. 62 (2023) e202218142. doi: 10.1002/anie.202218142
21. [21]
  L. Chen, Y. Wang, Y. Wan, et al., Chem. Eng. J. 387 (2020) 124087–124097. doi: 10.1016/j.cej.2020.124087
22. [22]
  K. Kato, S. Fa, S. Ohtani, et al., Chem. Soc. Rev. 51 (2022) 3648–3687. doi: 10.1039/d2cs00169a
23. [23]
  J.R. Wu, G. Wu, Y.W. Yang, et al., Acc. Chem. Res. 55 (2022) 3191–3204. doi: 10.1021/acs.accounts.2c00555
24. [24]
  C. Xiao, W. Wu, W. Liang, et al., Angew. Chem. Int. Ed. 59 (2020) 8094–8098. doi: 10.1002/anie.201916285
25. [25]
  J. Yao, W. Wu, C. Yang, et al., Nat. Commun. 12 (2021) 2600–2609;. doi: 10.1038/s41467-021-22880-z
26. [26]
  E. Lee, H. Ju, S.S. Lee, et al., J. Am. Chem. Soc. 140 (2018) 9669–9677. doi: 10.1021/jacs.8b05751
27. [27]
  W.B. Hu, H.M. Yang, W.J. Hu, et al., Chem. Commun. 50 (2014) 10460–10463. doi: 10.1039/C4CC01810A
28. [28]
  Y. Lv, C. Xiao, J. Ma, et al., Chin. Chem. Lett. 35 (2024) 108757. doi: 10.1016/j.cclet.2023.108757
29. [29]
  W.B. Hu, W.J. Hu, X.L. Zhao, et al., Chem. Commun. 51 (2015) 13882–13885. doi: 10.1039/C5CC05623C
30. [30]
  V. Singh, N. Singh, S.N. Rai, et al., Toxics 11 (2023) 147. doi: 10.3390/toxics11020147
31. [31]
  C. Ding, Y. Deng, A. Merchant, et al., Sep. Purif. Rev. 52 (2023) 123–134. doi: 10.1080/15422119.2022.2044352
32. [32]
  Q. Huang, Y. Zhang, W. Zhou, et al., Chin. Chem. Lett. 32 (2021) 2797–2802. doi: 10.1016/j.cclet.2020.12.020
33. [33]
  C. Bai, J. Zhang, Y. Qin, et al., Anal. Chem. 94 (2022) 11298–11306. doi: 10.1021/acs.analchem.2c01948
34. [34]
  W. Wu, N.J. Planavsky, Chem. Geol. 456 (2017) 98–111. doi: 10.1016/j.chemgeo.2017.03.009
35. [35]
  M. Costa, C.B. Klein, Crit. Rev. Toxicol. 36 (2006) 155–163. doi: 10.1080/10408440500534032
36. [36]
  J. Sun, P. Guo, M. Liu, et al., J. Mater. Chem. C 7 (2019) 8992–8999. doi: 10.1039/c9tc02666e
37. [37]
  X. Li, L. Jin, L. Huang, et al., J Environ. Chem. Eng. 9 (2021) 106357–106366. doi: 10.1016/j.jece.2021.106357
38. [38]
  R.J. Satya, C. Joyanta. J. Haz. Mat. 405 (2021) 124242–124251. doi: 10.1016/j.jhazmat.2020.124242
39. [39]
  X. Zhang, X. Wang, W. Fan, et al., Mater. Chem. Front. 4 (2020) 1150–1157. doi: 10.1039/c9qm00612e
40. [40]
  T. Ogoshi, S. Kanai, S. Fujinami, et al., J. Am. Chem. Soc. 2008 (13) 5022–5023. doi: 10.1021/ja711260m
41. [41]
  D.E. Zacharias, Acta Cryst. C 49 (1993) 1082–1087. doi: 10.1107/S0108270192013325
42. [42]
  M.M. Xu, X.J. Kong, T. He, et al., Inorg. Chem. 57 (2018) 14260–14268. doi: 10.1021/acs.inorgchem.8b02282
43. [43]
  A.M. Committee, Analyst 112 (1987) 199–204. doi: 10.1039/an9871200199
44. [44]
  J. Yoo, U. Ryu, K.M. Choi, Sensor Actuat B: Chem 283 (2019) 426–433. doi: 10.1016/j.snb.2018.12.031
45. [45]
  M.C. Lin, Inorg Chem. Commun. 105 (2019) 86–92. doi: 10.1016/j.inoche.2019.04.042
46. [46]
  J.X. Li, D. Liu, Z.C. Hao, et al., Inorg. Chem. Commun. 97 (2018) 79–82. doi: 10.1016/j.inoche.2018.09.018
47. [47]
  H.N. Chang, L.W. Liu, Z.C. Hao, et al., J. Mol. Struct. 1155 (2018) 496–502. doi: 10.1016/j.molstruc.2017.11.038
48. [48]
  N. Wu, Y. Li, M. Zeng, et al., Solid State Chem. 271 (2019) 292–297. doi: 10.1016/j.jssc.2019.01.015
49. [49]
  T. He, Y.Z. Zhang, X.J. Kong, et al., ACS Appl. Mater. Interfaces 10 (2018) 16650–16659. doi: 10.1021/acsami.8b03987
50. [50]
  H. Dang, H. Zou, S. Liu, et al., Dyes Pigments 172 (2020) 107804–107812. doi: 10.1016/j.dyepig.2019.107804
51. [51]
  Z.J. Li, Y.X. Ma, Q. Zhang, ACS Appl. Mater. Interfaces 11 (2019) 46197–46204. doi: 10.1021/acsami.9b17074
52. [52]
  Y. Wang, J. He, W. Wei, Talanta 191 (2019) 519–525. doi: 10.1016/j.talanta.2018.08.078
53. [53]
  M.J. Frisch, G.W. Trucks, H.B. Schlegel, et al., J. GAUSSIAN 09, Revision D.01, (Gaussian Inc.: Wallingford CT, 2013).
54. [54]
  W. Humphrey, A. Dalke, K. Schulten. J. Molec. Graphics 14 (1996) 33–38. doi: 10.1016/0263-7855(96)00018-5
55. [55]
  M.J. Frisch, J.A. Pople, J.S. Binkley, J. Chem. Phys. 80 (1984) 3265–3273. doi: 10.1063/1.447079
56. [56]
  T. Lu, F.W. Chen, J. Comput. Chem. 33 (2012) 580–592. doi: 10.1002/jcc.22885
57. [57]
  J. Rak, P. Skurski, J. Simons, et al., J. Am. Chem. Soc. 123 (2001) 11695–11707. doi: 10.1021/ja011357l
58. [58]
  D.P. Malenov, S.D. Zarić, Chem. Eur. J. 27 (2021) 17862–17872. doi: 10.1002/chem.202102896
59. [59]
  W. Charles Jr., Bauschlicher, Chem. Phys. Lett. 694 (2018) 86–92. doi: 10.4324/9780203712955-8
60. [60]
  C. Lefebvre, G. Rubez, H. Khartabil, et al., Chem. Chem. Phys. 19 (2017) 17928–17936. doi: 10.1039/C7CP02110K
61. [61]
  T. Lu, Q. Chen, J. Comput. Chem. 43 (2022) 539–555. doi: 10.1002/jcc.26812
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A novel fused bi-macrocyclic host for sensitive detection of Cr2O72− based on enrichment effect

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通讯作者: 陈斌, bchen63@163.com

A novel fused bi-macrocyclic host for sensitive detection of Cr₂O₇²⁻ based on enrichment effect