Citation: Ya-Liang Lai, Juan Su, Le-Xiong Wu, Dong Luo, Xue-Zhi Wang, Xian-Chao Zhou, Chuang-Wei Zhou, Xiao-Ping Zhou, Dan Li. Selective separation of pyrene from mixed polycyclic aromatic hydrocarbons by a hexahedral metal-organic cage[J]. Chinese Chemical Letters, ;2024, 35(1): 108326. doi: 10.1016/j.cclet.2023.108326 shu

Selective separation of pyrene from mixed polycyclic aromatic hydrocarbons by a hexahedral metal-organic cage

College of Chemistry and Materials Science, Guangdong Provincial Key Laboratory of Functional Supramolecular Coordination Materials and Applications, Jinan University, Guangzhou 510632, China

zhouxp@jnu.edu.cn

Received Date: 23 December 2022
Revised Date: 10 February 2023
Accepted Date: 8 March 2023
Available Online: 11 March 2023

Figures(7)

Polycyclic aromatic hydrocarbons (PAHs) play an important role in the industry, and the development of new materials for the selective separation of PAHs is of great significance. In this work, we report a hexahedral metal-organic cage with low symmetry by subcomponent self-assembly. In this cage, the eight Zn^Ⅱ centers adopt an interesting ΛΛ/ΔΔΔΔΔΔ or ΛΛΛΛΛΛ/ΔΔ configuration. This cage with a cavity volume of 520 Å³ can bind anthracene, phenanthrene, and pyrene to form 1:1 host-guest complexes, while the bigger triphenylene, chrysene, perylene, and coronene cannot be encapsulated. The binding constant K_a of pyrene is about 1.110 × 10³ (mol/L)⁻¹_, which is more than an order of magnitude larger than that of anthracene and phenanthrene (111 (mol/L)⁻¹, 277 (mol/L)⁻¹, respectively). X-ray structure studies reveal that the pyrene is located in the cavity and stabilized by multiple CH⋅⋅⋅π interactions. After separation from a mixture of PAHs, pyrene with > 96.1% purity can be obtained. This work provides a useful method for the first time for the selective separation of pyrene from PAHs mixture by utilizing a metal-organic cage as the material, making it a useful tool for purifying and separating specific compounds from complex mixtures.
- Polycyclic aromatic hydrocarbons,
- Metal-organic cage,
- Host-guest chemistry,
- Selective separation
1. [1]
  V. Kumar, N.C. Kothiyal, et al., J. Chin. Adv. Mater. Soc. 4 (2016) 302–321. doi: 10.1080/22243682.2016.1230475
2. [2]
  I.J. Keyte, R.M. Harrison, G. Lammel, Chem. Soc. Rev. 42 (2013) 9333–9391. doi: 10.1039/c3cs60147a
3. [3]
  F.P. Kinik, A. Ortega-Guerrero, D. Ongari, et al., Chem. Soc. Rev. 50 (2021) 3143–3177. doi: 10.1039/D0CS00424C
4. [4]
  T.M. Figueira-Duarte, K. Müllen, Chem. Rev. 111 (2011) 7260–7314. doi: 10.1021/cr100428a
5. [5]
  F.M. Winnik, Chem. Rev. 93 (1993) 587–614. doi: 10.1021/cr00018a001
6. [6]
  A.J. Howarth, M.B. Majewski, M.O. Wolf, Coord. Chem. Rev. 282-283 (2015) 139–149. doi: 10.1016/j.ccr.2014.03.024
7. [7]
  M. Zhao, Y. Huang, Y. Peng, et al., Chem. Soc. Rev. 47 (2018) 6267–6295. doi: 10.1039/C8CS00268A
8. [8]
  N. Stock, S. Biswas, Chem. Rev. 112 (2012) 933–969. doi: 10.1021/cr200304e
9. [9]
  E.S.M. El-Sayed, Y.D. Yuan, D. Zhao, et al., Acc. Chem. Res. 55 (2022) 1546–1560. doi: 10.1021/acs.accounts.1c00654
10. [10]
  S. Daliran, A.R. Oveisi, Y. Peng, et al., Chem. Soc. Rev. 51 (2022) 7810–7882. doi: 10.1039/D1CS00976A
11. [11]
  T.R. Cook, P.J. Stang, Chem. Rev. 115 (2015) 7001–7045. doi: 10.1021/cr5005666
12. [12]
  A.J. Gosselin, C.A. Rowland, E.D. Bloch, Chem. Rev. 120 (2020) 8987–9014. doi: 10.1021/acs.chemrev.9b00803
13. [13]
  L.J. Wang, X. Li, S. Bai, et al., J. Am. Chem. Soc. 142 (2020) 2524–2531. doi: 10.1021/jacs.9b12309
14. [14]
  L.J. Wang, S. Bai, Y.F. Han, J. Am. Chem. Soc. 144 (2022) 16191–16198. doi: 10.1021/jacs.2c07586
15. [15]
  D. Zhang, T.K. Ronson, Y.-Q. Zou, et al., Nat. Rev. Chem. 5 (2021) 168–182. doi: 10.1038/s41570-020-00246-1
16. [16]
  C. Zhu, H. Tang, K. Yang, et al., J. Am. Chem. Soc. 143 (2021) 12560–12566. doi: 10.1021/jacs.1c03652
17. [17]
  D. Chakraborty, R. Saha, J.K. Clegg, et al., Chem. Sci. 13 (2022) 11764–11771. doi: 10.1039/D2SC04660A
18. [18]
  W.Y. Zhang, Y.J. Lin, Y.F. Han, et al., J. Am. Chem. Soc. 138 (2016) 10700–10707. doi: 10.1021/jacs.6b06622
19. [19]
  Y. Fang, J.A. Powell, E. Li, et al., Chem. Soc. Rev. 48 (2019) 4707–4730. doi: 10.1039/C9CS00091G
20. [20]
  Y. Xue, X. Hang, J. Ding, et al., Coord. Chem. Rev. 430 (2021) 213656. doi: 10.1016/j.ccr.2020.213656
21. [21]
  R.L. Spicer, A.D. Stergiou, T.A. Young, et al., J. Am. Chem. Soc. 142 (2020) 2134–2139. doi: 10.1021/jacs.9b11273
22. [22]
  M. Pan, K. Wu, J.H. Zhang, et al., Coord. Chem. Rev. 378 (2019) 333–349. doi: 10.1016/j.ccr.2017.10.031
23. [23]
  W. Xuan, M. Zhang, Y. Liu, et al., J. Am. Chem. Soc. 134 (2012) 6904–6907. doi: 10.1021/ja212132r
24. [24]
  A. Brzechwa-Chodzyńska, W. Drożdż, J. Harrowfield, et al., Coord. Chem. Rev. · 434 (2021) 213820. doi: 10.1016/j.ccr.2021.213820
25. [25]
  Z. Zhang, Z. Zhao, L. Wu, et al., J. Am. Chem. Soc. 142 (2020) 2592–2600. doi: 10.1021/jacs.9b12689
26. [26]
  P. Mal, B. Breiner, K. Rissanen, et al., Science 324 (2009) 1697–1699. doi: 10.1126/science.1175313
27. [27]
  S. Hasegawa, S.L. Meichsner, J.J. Holstein, et al., J. Am. Chem. Soc. 143 (2021) 9718–9723. doi: 10.1021/jacs.1c02860
28. [28]
  Y.R. Zheng, K. Suntharalingam, T.C. Johnstone, et al., Chem. Sci. 6 (2015) 1189–1193. doi: 10.1039/C4SC01892C
29. [29]
  H. Sepehrpour, W. Fu, Y. Sun, et al., J. Am. Chem. Soc. 141 (2019) 14005–14020. doi: 10.1021/jacs.9b06222
30. [30]
  F.J. Rizzuto, L.K.S. von Krbek, J.R. Nitschke, Nat. Rev. Chem. 3 (2019) 204–222. doi: 10.1038/s41570-019-0085-3
31. [31]
  M. Yamashina, Y. Tanaka, R. Lavendomme, et al., Nature 574 (2019) 511–515. doi: 10.1038/s41586-019-1661-x
32. [32]
  D. Zhang, T.K. Ronson, R. Lavendomme, et al., J. Am. Chem. Soc. 141 (2019) 18949–18953. doi: 10.1021/jacs.9b10741
33. [33]
  A.B. Sainaba, M. Venkateswarulu, P. Bhandari, et al., J. Am. Chem. Soc. 144 (2022) 7504–7513. doi: 10.1021/jacs.2c02540
34. [34]
  S. Sun, L. Huang, H. Xiao, et al., Talanta 202 (2019) 145–151. doi: 10.1016/j.talanta.2019.04.063
35. [35]
  M. Tabatabaii, M. Khajeh, A.R. Oveisi, et al., ACS Omega 5 (2020) 12202–12209. doi: 10.1021/acsomega.0c00687
36. [36]
  C.T. McTernan, J.A. Davies, J.R. Nitschke, Chem. Rev. 122 (2022) 10393–10437. doi: 10.1021/acs.chemrev.1c00763
37. [37]
  H.L. Nguyen, C. Gropp, Y. Ma, et al., J. Am. Chem. Soc. 142 (2020) 20335–20339. doi: 10.1021/jacs.0c11064
38. [38]
  J.T. Edward, J. Chem. Educ. 47 (1970) 261. doi: 10.1021/ed047p261
39. [39]
  H. Wang, C. Guo, X. Li, CCS Chem. 4 (2022) 785–808. doi: 10.31635/ccschem.021.202101408
40. [40]
  W. Meng, J.K. Clegg, J.D. Thoburn, et al., J. Am. Chem. Soc. 133 (2011) 13652–13660. doi: 10.1021/ja205254s
41. [41]
  J. Jiao, Z. Li, Z. Qiao, et al., Nat. Commun. 9 (2018) 4423. doi: 10.1038/s41467-018-06872-0
42. [42]
  D. Luo, L.X. Wu, Y. Zhang, et al., Sci. China Chem. 65 (2022) 1105–1111. doi: 10.1007/s11426-022-1245-1
43. [43]
  W. Meng, B. Breiner, K. Rissanen, et al., Angew. Chem. Int. Ed. 50 (2011) 3479–3483. doi: 10.1002/anie.201100193
44. [44]
  G.J. Kleywegt, T.A. Jones, Acta Crystallogr. Sect. D 50 (1994) 178–185. doi: 10.1107/S0907444993011333
45. [45]
  P. Mal, D. Schultz, K. Beyeh, et al., Angew. Chem. Int. Ed. 47 (2008) 8297–8301. doi: 10.1002/anie.200803066
46. [46]
  S. Mecozzi, J. Rebek, Julius, Chem. Eur. J. 4 (1998) 1016–1022. doi: 10.1002/(SICI)1521-3765(19980615)4:6<1016::AID-CHEM1016>3.0.CO;2-B
47. [47]
  T. Feng, X. Li, J. Wu, et al., Chin. Chem. Lett. 31 (2020) 95–98. doi: 10.1016/j.cclet.2019.04.059
48. [48]
  B.S. Pilgrim, N.R. Champness, ChemPlusChem 85 (2020) 1842–1856. doi: 10.1002/cplu.202000408
49. [49]
  T. Lu, Q. Chen, J. Comput. Chem. 43 (2022) 539–555. doi: 10.1002/jcc.26812
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3. [3]
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