Citation: Ying-Mei Zhong, Zi-Jun Xia, Yu-Hang Hu, Li-Peng Zhou, Li-Xuan Cai, Qing-Fu Sun. Effective separation of phenanthrene from isomeric anthracene using a water-soluble macrocycle-based cage[J]. Chinese Chemical Letters, ;2025, 36(4): 110164. doi: 10.1016/j.cclet.2024.110164 shu

Effective separation of phenanthrene from isomeric anthracene using a water-soluble macrocycle-based cage

Ying-Mei Zhong ^{a, b, c} ,
Zi-Jun Xia ^b ,
Yu-Hang Hu ^{a, b, c} ,
Li-Peng Zhou ^{a, b, c} ,
Li-Xuan Cai ^{a, b, c, **,} ,
Qing-Fu Sun ^{a, b, c, *,}

a.
College of Chemistry and Materials Science, Fujian Normal University, Fuzhou 350007, China
b.
State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou 350002, China
c.
University of Chinese Academy of Sciences, Beijing 100049, China

^**

lxcai@fjirsm.ac.cn

qfsun@fjirsm.ac.cn

Received Date: 1 March 2024
Revised Date: 4 June 2024
Accepted Date: 21 June 2024
Available Online: 22 June 2024

Figures(5)

Selective separation of phenanthrene (PHE) from aromatic isomer mixtures poses a significant challenge in industry due to the similar physical properties of PHE and its isomer anthracene (ANT). Herein, we report the self-assembly of a water-soluble Pd₂L₂ cage 1 with a large hydrophobic cavity, formed from novel macrocyclic ligands (L) and cis-Pd(Ⅱ). Cage 1 can selectively encapsulate PHE instead of ANT. Based on host-guest recognition followed by extraction, we achieve a remarkable 99% purity of PHE separation from an equimolar mixture of PHE and ANT using cage 1 in aqueous solution. Importantly, the separation performance of PHE using cage 1 remains unaffected even after five extraction cycles, demonstrating its robustness. This work highlights the potential of supramolecular cages for efficient and cost-effective PHE separation from the isomer ANT in aqueous solutions using such promising host-guest strategy.
- Coordination cage,
- Host-guest chemistry,
- Selective separation
1. [1]
  M. Li, C. An, T. Marszalek, et al., Chem. Mater. 27 (2015) 2218–2223. doi: 10.1021/acs.chemmater.5b00341
2. [2]
  D.R. Vinayakumara, H. Ulla, S. Kumar, et al., Mater. Chem. Front. 2 (2018) 2297–2306. doi: 10.1039/c8qm00377g
3. [3]
  S. Kataoka, H. Fukumoto, T. Kawasaki-Takasuka, et al., J. Fluorine Chem. 218 (2019) 84–89.
4. [4]
  G. Asaithambi, V. Periasamy, Res. Chem. Intermed. 45 (2018) 1295–1308.
5. [5]
  A. Burel, S.J.T. Brugman, M. Mignot, et al., Chem. Eng. Technol. 39 (2016) 1317–1325. doi: 10.1002/ceat.201600033
6. [6]
  N. Couvrat, A. Burel, S. Tisse, et al., J. Therm. Anal. Calorim. 112 (2012) 293–300.
7. [7]
  O.N. Pavlovich, Coke Chem. 55 (2012) 247–248.
8. [8]
  Y. Yang, M. Liu, L. Wang, et al., Mar. Pollut. Bull. 62 (2011) 1025–1031.
9. [9]
  M. Patejko, J. Jacyna, M.J. Markuszewski, J. Chromatogr. B 1043 (2017) 150–157. doi: 10.1016/j.jchromb.2016.09.029
10. [10]
  C.E. Nazario, B.H. Fumes, M.R. da Silva, et al., J. Chromatogr. B 1043 (2017) 81–95. doi: 10.1016/j.jchromb.2016.10.041
11. [11]
  O. Filippou, D. Bitas, V. Samanidou, J. Chromatogr. B 1043 (2017) 44–62.
12. [12]
  M. Yamashina, Y. Sei, M. Akita, et al., Nat. Commun. 5 (2014) 4662.
13. [13]
  D. Luo, B. Pan, J. Zhang, et al., Chin. Chem. Lett. 32 (2021) 1397–1399.
14. [14]
  Y.L. Lai, H.J. Zhang, J. Su, et al., Chin. Chem. Lett. 34 (2023) 107686.
15. [15]
  M. Morimoto, S.M. Bierschenk, K.T. Xia, et al., Nat. Catal. 3 (2020) 969–984. doi: 10.1038/s41929-020-00528-3
16. [16]
  L. Jia, X. Tang, Y. Cui, et al., Sci. Chin. Chem. 66 (2023) 2169–2180. doi: 10.1007/s11426-023-1607-4
17. [17]
  K. Wang, X. Tang, B.A. Anjali, et al., J. Am. Chem. Soc. 146 (2024) 6638–6651. doi: 10.1021/jacs.3c12555
18. [18]
  M. Pan, K. Wu, J.H. Zhang, et al., Coord. Chem. Rev. 378 (2019) 333–349.
19. [19]
  Q. Chen, Z. Li, Y. Lei, et al., Nat. Commun. 14 (2023) 4627. doi: 10.1038/s41467-023-40255-4
20. [20]
  Z. Zhang, Y. Yao, L. He, et al., Chin. Chem. Lett. 34 (2023) 107521. doi: 10.1016/j.cclet.2022.05.035
21. [21]
  C. Li, Y. Wang, Y. Lu, et al., Chin. Chem. Lett. 31 (2020) 1183–1187.
22. [22]
  S.J. Hu, X.Q. Guo, L.P. Zhou, et al., Chin. J. Chem 41 (2023) 797–804. doi: 10.1002/cjoc.202200649
23. [23]
  D. Samanta, D. Galaktionova, J. Gemen, et al., Nat. Commun. 9 (2018) 641–649.
24. [24]
  L.J. Wang, X. Li, S. Bai, et al., J. Am. Chem. Soc. 142 (2020) 2524–2531. doi: 10.1021/jacs.9b12309
25. [25]
  A. Sorensen, A.M. Castilla, T.K. Ronson, et al., Angew. Chem. Int. Ed. 52 (2013) 11273–11277. doi: 10.1002/anie.201305245
26. [26]
  O. Yanshyna, M.J. Bialek, O.V. Chashchikhin, et al., Commun. Chem. 5 (2022) 44.
27. [27]
  J. Wang, C. He, P. Wu, et al., J. Am. Chem. Soc. 133 (2011) 12402–12405. doi: 10.1021/ja2048489
28. [28]
  D. Chakraborty, S. Ali, P. Choudhury, et al., J. Am. Chem. Soc. 145 (2023) 26973–26982. doi: 10.1021/jacs.3c10191
29. [29]
  K. Hema, A.B. Grommet, M.J. Bialek, et al., J. Am. Chem. Soc. 145 (2023) 24755–24764.
30. [30]
  L.P. Zhou, X.S. Feng, S.J. Hu, et al., J. Am. Chem. Soc. 145 (2023) 17845–17855. doi: 10.1021/jacs.3c04921
31. [31]
  Y. Yang, T.K. Ronson, J. Zheng, et al., Chem 9 (2023) 1972–1982. doi: 10.1016/j.chempr.2023.03.027
32. [32]
  X. Huang, L. Chen, J. Jin, et al., Inorg. Chem. 61 (2022) 20237–20242. doi: 10.1021/acs.inorgchem.2c03701
33. [33]
  B. Shi, K. Jie, Y. Zhou, et al., J. Am. Chem. Soc. 138 (2016) 80–83. doi: 10.1021/jacs.5b11676
34. [34]
  S.M. Biros, J. Rebek Jr., Chem. Soc. Rev. 36 (2007) 93–104. doi: 10.1039/B508530F
35. [35]
  Z. Laughrey, B.C. Gibb, Chem. Soc. Rev. 40 (2011) 363–386. doi: 10.1039/C0CS00030B
36. [36]
  M. Whitehead, S. Turega, A. Stephenson, et al., Chem. Sci. 4 (2013) 2744–2751. doi: 10.1039/c3sc50546d
37. [37]
  C. Jose, M. Sarkar, P. Rajasekar, et al., Inorg. Chem. 62 (2023) 19375–19381. doi: 10.1021/acs.inorgchem.3c03105
38. [38]
  P.J. Gilissen, Q. Duez, G.L. Tripodi, et al., Chem. Commun. 59 (2023) 13974–13977. doi: 10.1039/d3cc04934e
39. [39]
  Y.H. Huang, Y.L. Lu, X.D. Zhang, et al., Angew. Chem. Int. Ed. 63 (2024) e202315053. doi: 10.1002/anie.202315053
40. [40]
  L. Yang, N. Song, D. Zhang, et al., Inorg. Chem. 62 (2023) 17705–17712. doi: 10.1021/acs.inorgchem.3c02331
41. [41]
  D. Kim, J. Park, G. Kim, et al., Inorg. Chem. 62 (2023) 10605–10612. doi: 10.1021/acs.inorgchem.3c00823
42. [42]
  C. Zhao, F.D. Toste, K.N. Raymond, et al., J. Am. Chem. Soc. 136 (2014) 14409–14412. doi: 10.1021/ja508799p
43. [43]
  W. Cullen, H. Takezawa, M. Fujita, Angew. Chem. Int. Ed. 58 (2019) 9171–9173. doi: 10.1002/anie.201904752
44. [44]
  J. Guo, Y.W. Xu, K. Li, et al., Angew. Chem. Int. Ed. 56 (2017) 3852–3856. doi: 10.1002/anie.201611875
45. [45]
  Z.J. Wang, C.J. Brown, R.G. Bergman, et al., J. Am. Chem. Soc. 133 (2011) 7358–7360. doi: 10.1021/ja202055v
46. [46]
  C. Tan, J. Jiao, Z. Li, et al., Angew. Chem. Int. Ed. 57 (2018) 2085–2090. doi: 10.1002/anie.201711310
47. [47]
  K. Iizuka, H. Takezawa, M. Fujita, J. Am. Chem. Soc. 145 (2023) 25971–25975. doi: 10.1021/jacs.3c10720
48. [48]
  Y. Yang, H. Li, Y. Shi, et al., Angew. Chem. Int. Ed. 63 (2024) e202319605. doi: 10.1002/anie.202319605
49. [49]
  S.M. Bierschenk, J.Y. Pan, N.S. Settineri, et al., J. Am. Chem. Soc. 144 (2022) 11425–11433. doi: 10.1021/jacs.2c04182
50. [50]
  Q.N.N. Nguyen, K.T. Xia, Y. Zhang, et al., J. Am. Chem. Soc. 144 (2022) 11413–11424. doi: 10.1021/jacs.2c04179
51. [51]
  D. Liu, H. Ma, C. Zhu, et al., J. Am. Chem. Soc. 146 (2024) 2275–2285. doi: 10.1021/jacs.3c14254
52. [52]
  Y.L. Lu, Y.H. Qin, S.-P. Zheng, et al., ACS Catal. 14 (2023) 94–103.
53. [53]
  D.N. Yan, L.X. Cai, P.M. Cheng, et al., J. Am. Chem. Soc. 143 (2021) 16087–16094. doi: 10.1021/jacs.1c06390
54. [54]
  T.P. Sheng, C. He, Z. Wang, et al., CCS Chem. 4 (2022) 1098–1107. doi: 10.31635/ccschem.021.202100987
55. [55]
  S.K. Samanta, D. Moncelet, V. Briken, et al., J. Am. Chem. Soc. 138 (2016) 14488–14496. doi: 10.1021/jacs.6b09504
56. [56]
  D. Zhang, T.K. Ronson, J.R. Nitschke, Acc. Chem. Res. 51 (2018) 2423–2436. doi: 10.1021/acs.accounts.8b00303
57. [57]
  F. Schmitt, J. Freudenreich, N.P. Barry, et al., J. Am. Chem. Soc. 134 (2012) 754–757. doi: 10.1021/ja207784t
58. [58]
  J.E.M. Lewis, E.L. Gavey, S.A. Cameron, et al., Chem. Sci. 3 (2012) 778–784. doi: 10.1039/C2SC00899H
59. [59]
  X. Li, W. Lin, V. Sharma, et al., Nat. Commun. 14 (2023) 3112. doi: 10.1109/tnet.2023.3270565
60. [60]
  Y. Wang, R. Tang, D. Wang, et al., Inorg. Chem. 62 (2023) 1786–1790. doi: 10.1021/acs.inorgchem.2c01206
61. [61]
  S. Fang, M. Wang, Y. Wu, et al., Chem. Sci. 13 (2022) 6254–6261. doi: 10.1039/d2sc01782b
62. [62]
  N. Kishi, Z. Li, K. Yoza, et al., J. Am. Chem. Soc. 133 (2011) 11438–11441. doi: 10.1021/ja2037029
63. [63]
  P. Mal, D. Schultz, K. Beyeh, et al., Angew. Chem. Int. Ed. 47 (2008) 8297–8301. doi: 10.1002/anie.200803066
64. [64]
  A. Walther, I. Regeni, J.J. Holstein, et al., J. Am. Chem. Soc. 145 (2023) 25365–25371. doi: 10.1021/jacs.3c09295
65. [65]
  J.R. Wu, Y.W. Yang, Angew. Chem. Int. Ed. 60 (2021) 1690–1701. doi: 10.1002/anie.202006999
66. [66]
  D. Zhang, T.K. Ronson, R. Lavendomme, et al., J. Am. Chem. Soc. 141 (2019) 18949–18953. doi: 10.1021/jacs.9b10741
67. [67]
  L.J. Wang, S. Bai, Y.F. Han, J. Am. Chem. Soc. 144 (2022) 16191–16198. doi: 10.1021/jacs.2c07586
68. [68]
  Y.L. Lai, J. Su, L.X. Wu, et al., Chin. Chem. Lett. 35 (2024) 108326. doi: 10.1016/j.cclet.2023.108326
69. [69]
  L. Tong, D. Zhu, B. Chen, et al., Org. Lett. 23 (2021) 9343–9347. doi: 10.1021/acs.orglett.1c03154
70. [70]
  G. Wu, C.Y. Wang, T. Jiao, et al., J. Am. Chem. Soc. 140 (2018) 5955–5961. doi: 10.1021/jacs.8b01651
71. [71]
  Y. Liu, H. Wang, L. Shangguan, et al., J. Am. Chem. Soc. 143 (2021) 3081–3085. doi: 10.1021/jacs.1c01204
72. [72]
  A.B. Sainaba, M. Venkateswarulu, P. Bhandari, et al., J. Am. Chem. Soc. 144 (2022) 7504–7513. doi: 10.1021/jacs.2c02540
73. [73]
  D. Prajapati, P. Bhandari, N. Hickey, et al., Inorg. Chem. 62 (2023) 9230–9239. doi: 10.1021/acs.inorgchem.3c01156
74. [74]
  D.D. Boehr, R. Nussinov, P.E. Wright, Nat. Chem. Biol. 5 (2009) 789–796. doi: 10.1038/nchembio.232
75. [75]
  C.J. Brown, F.D. Toste, R.G. Bergman, et al., Chem. Rev. 115 (2015) 3012–3035. doi: 10.1021/cr4001226
76. [76]
  S. De, K. Mahata, M. Schmittel, Chem. Soc. Rev. 39 (2010) 1555–1575. doi: 10.1039/b922293f
77. [77]
  J. Gemen, M.J. Bialek, M. Kazes, et al., Chem 8 (2022) 2362–2379. doi: 10.1016/j.chempr.2022.05.008
78. [78]
  S.L. Huang, Y.J. Lin, T.S. Hor, et al., J. Am. Chem. Soc. 135 (2013) 8125–8128. doi: 10.1021/ja402630g
79. [79]
  H. Li, Z.J. Yao, D. Liu, et al., Coord. Chem. Rev. 293–294 (2015) 139–157.
80. [80]
  T.K. Ronson, J.P. Carpenter, J.R. Nitschke, Chem 8 (2022) 557–568. doi: 10.1016/j.chempr.2021.12.017
81. [81]
  Y. Tamura, H. Takezawa, M. Fujita, J. Am. Chem. Soc. 142 (2020) 5504–5508. doi: 10.1021/jacs.0c00459
82. [82]
  J. Mosquera, T.K. Ronson, J.R. Nitschke, J. Am. Chem. Soc. 138 (2016) 1812–1815. doi: 10.1021/jacs.5b12955
83. [83]
  T. Sawada, H. Hisada, M. Fujita, J. Am. Chem. Soc. 136 (2014) 4449–4451. doi: 10.1021/ja500376x
84. [84]
  Z.J. Xia, Y.M. Zhong, S.J. Hu, et al., Inorg. Chem. 62 (2023) 8293–8299. doi: 10.1021/acs.inorgchem.3c00762
85. [85]
  D.N. Yan, L.X. Cai, S.J. Hu, et al., Angew. Chem. Int. Ed. 61 (2022) e202209879. doi: 10.1002/anie.202209879
86. [86]
  J.B. Maglic, R. Lavendomme, J. Appl. Crystallogr. 55 (2022) 1033–1044. doi: 10.1107/s1600576722004988
87. [87]
  X. Wang, M.L. Brusseau, Environ. Sci. Technol. 29 (1995) 2346–2351. doi: 10.1021/es00009a029
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