Citation: Jingxiong Jiang, Yao Dong, Yuchun Wang, Lijuan Qi, Zhen-Yu Li, Tai-Bao Wei, Wen-Juan Qu, Qi Lin, Bingbing Shi. Separation of toluene-alcohol azeotropes by porous crystals of fluorinated leaning pillar[6]arene[J]. Chinese Chemical Letters, ;2025, 36(8): 110759. doi: 10.1016/j.cclet.2024.110759 shu

Separation of toluene-alcohol azeotropes by porous crystals of fluorinated leaning pillar[6]arene

Key Laboratory of Eco-Functional Polymer Materials of the Ministry of Education, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070, China

linqi2004@126.com

bingbingshi@nwnu.edu.cn

Received Date: 8 October 2024
Revised Date: 3 December 2024
Accepted Date: 11 December 2024
Available Online: 14 December 2024

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Herein we report an environmentally friendly and energy-efficient method for the adsorptive separation of toluene from toluene-alcohol azeotropes using porous crystalline fluorinated leaning pillar[6]arene (FLP6α), achieving up to 100% purity. Moreover, FLP6α demonstrates rapid adsorption and excellent recyclability.
- Pillar[6]arene,
- Macrocyclic host,
- Host–guest interactions,
- Porous material,
- Adsorption and separation
1. [1]
  G. Zhao, Y. Wang, L. Xie, et al., Sep. Purif. Technol. 353 (2025) 128478.
2. [2]
  U. Anggarini, L. Yu, H. Nagasawa, et al., ACS Appl. Mater. Interfaces 13 (2021) 23247–23259. doi: 10.1021/acsami.1c05012
3. [3]
  G. Genduso, H. Farrokhzad, Y. Latré, et al., J. Membr. Sci. 482 (2015) 128–136.
4. [4]
  M. Yan, Y. Wang, J. Chen, et al., Chem. Soc. Rev. 52 (2023) 6075–6119. doi: 10.1039/d2cs00856d
5. [5]
  G. Zhang, W. Lin, F. Huang, et al., J. Am. Chem. Soc. 145 (2023) 19143–19163. doi: 10.1021/jacs.3c06175
6. [6]
  F.S. Oliveira, A.B. Pereiro, L.P.N. Rebelo, et al., Green. Chem. 15 (2013) 1326–1330. doi: 10.1039/c3gc37030e
7. [7]
  W.L. Chang, I.L. Chien, Ind. Eng. Chem. Res. 55 (2016) 3064–3074. doi: 10.1021/acs.iecr.6b00391
8. [8]
  M.Y. Zhou, X.W. Zhang, H. Yi, et al., J. Am. Chem. Soc. 146 (2024) 12969–12975. doi: 10.1021/jacs.3c13480
9. [9]
  I.J. Jupiter, J.D. Loya, N. Lutz, et al., Cryst. Growth Des. 24 (2024) 5883–5888. doi: 10.1021/acs.cgd.4c00125
10. [10]
  K. Banjerdteerakul, H. Peng, K. Li, J. Membr. Sci. 678 (2023) 121679.
11. [11]
  H. Sun, F. Wang, X. Li, et al., Angew. Chem. Int. Ed. 62 (2023) e202300262.
12. [12]
  M.B. Patil, T.M. Aminabhavi, Sep. Purif. Technol. 62 (2008) 128–136.
13. [13]
  M. Yan, Y. Wang, J. Zhou, Cell Rep. Phys. Sci. 4 (2023) 101637.
14. [14]
  C.J. Pedersen, J. Am. Chem. Soc. 89 (1967) 2495–2496. doi: 10.1021/ja00986a052
15. [15]
  Y. Chen, Y. Liu, Chem. Soc. Rev. 39 (2010) 495–505.
16. [16]
  A. Harada, Acc. Chem. Res. 34 (2001) 456–464.
17. [17]
  X.N. Han, Y. Han, C.F. Chen, Chem. Soc. Rev. 52 (2023) 3265–3298. doi: 10.1039/d3cs00002h
18. [18]
  W. Qian, M. Zuo, P. Niu, et al., Chin. Chem. Lett. 33 (2022) 1975–1978.
19. [19]
  Y. Chai, P. Qin, X. Li, et al., Chin. J. Chem. 40 (2022) 2421–2427. doi: 10.1002/cjoc.202200361
20. [20]
  C. Yang, Y. Inoue, Chem. Soc. Rev. 43 (2014) 4123–4143.
21. [21]
  Y. Mei, Q.W. Zhang, Q. Gu, et al., J. Am. Chem. Soc. 144 (2022) 2351–2359. doi: 10.1021/jacs.1c12959
22. [22]
  X. Tan, Z. Zhang, T. Cao, et al., ACS Sustain. Chem. Eng. 7 (2019) 20051–20059. doi: 10.1021/acssuschemeng.9b05804
23. [23]
  T. Ogoshi, S. Kanai, S. Fujinami, et al., J. Am. Chem. Soc. 130 (2008) 5022–5023. doi: 10.1021/ja711260m
24. [24]
  D.S. Guo, Y. Liu, Acc. Chem. Res. 47 (2014) 1925–1934. doi: 10.1021/ar500009g
25. [25]
  W.L. Huang, X.D. Wang, Y.F. Ao, et al., Chem. Commun. 59 (2023) 14689–14692. doi: 10.1039/d3cc04573k
26. [26]
  B. Li, L. Liu, Y. Wang, et al., Nat. Commun. 15 (2024) 2535.
27. [27]
  L. Tong, D. Zhu, B. Chen, et al., Org. Lett. 23 (2021) 9343–9347. doi: 10.1021/acs.orglett.1c03154
28. [28]
  X.N. Han, Y. Han, C.F. Chen, J. Am. Chem. Soc. 142 (2020) 8262–8269. doi: 10.1021/jacs.0c00624
29. [29]
  L. Cao, L. Isaacs, Org. Lett. 14 (2012) 3072–3075. doi: 10.1021/ol3011425
30. [30]
  Y. Ding, J. Jiao, B. Sun, et al., Chin. Chem. Lett. 32 (2021) 3539–3543.
31. [31]
  T. Ogoshi, S. Kanai, S. Fujinami, et al., J. Am. Chem. Soc. 130 (2008) 5022–5023. doi: 10.1021/ja711260m
32. [32]
  W.L. Guan, J.F. Chen, J. Liu, et al., Coord. Chem. Rev. 507 (2024) 215717.
33. [33]
  W.H. Mi, T.Y. Huang, Y.F. Ao, et al., Chin. Chem. Lett. 35 (2024) 109077.
34. [34]
  J. Ji, X. Wei, W. Wu, et al., Acc. Chem. Res. 56 (2023) 1896–1907. doi: 10.1021/acs.accounts.3c00234
35. [35]
  W. Li, P. Qin, X.X. Zhao, et al., Org. Biomol. Chem. 20 (2022) 9122–9126. doi: 10.1039/d2ob01579j
36. [36]
  B. Shi, W. Li, P. Qin, et al., ChemNanoMat. 9 (2023) e202300156.
37. [37]
  B. Moosa, L.O. Alimi, W. Lin, et al., Angew. Chem. Int. Ed. 62 (2023) e202311555.
38. [38]
  B. Shi, J. Jiang, H. An, et al., J. Am. Chem. Soc. 146 (2024) 2901–2906. doi: 10.1021/jacs.3c13714
39. [39]
  B. Zhao, J. Wang, L. Shao, et al., Chem. Commun. 59 (2023) 10432–10435. doi: 10.1039/d3cc03676f
40. [40]
  Y. Zhou, K. Jie, R. Zhao, et al., Adv. Mater. 32 (2020) 1904824.
41. [41]
  B. Lu, X. Yan, J. Wang, et al., Chem. Commun. 58 (2022) 2480–2483. doi: 10.1039/d1cc07124f
42. [42]
  J. Cao, Y. Wu, Q. Li, et al., Chem. Sci. 13 (2022) 7536–7540. doi: 10.1039/d2sc02494b
43. [43]
  B. Hua, Y. Ding, L.O. Alimi, et al., Chem. Sci. 12 (2021) 12286–12291. doi: 10.1039/d1sc03509f
44. [44]
  G. Zhang, K. Zhang, X.-Y. Lou, et al., ACS Mater. Lett. 6 (2024) 446–451. doi: 10.1021/acsmaterialslett.3c01250
45. [45]
  B. Li, Y. Wang, Y. Wang, et al., Chem. Commun. 60 (2024) 6889–6892. doi: 10.1039/d4cc01246a
46. [46]
  F. Zeng, L.L. Tang, H. Yu, et al., Chin. Chem. Lett. 34 (2023) 108304.
47. [47]
  T. Lu, F. Chen, J. Comput. Chem. 33 (2012) 580–592. doi: 10.1002/jcc.22885
48. [48]
  T. Lu, Q. Chen, J. Comput. Chem. 43 (2022) 539–555. doi: 10.1002/jcc.26812
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2. [2]
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