Citation: Rongjian Chen, Jiahui Liu, Caixia Lin, Yuanming Li, Yanhou Geng, Yaofeng Yuan. Synthesis and properties of tetraphenylethene cationic cyclophanes based on o-carborane skeleton[J]. Chinese Chemical Letters, ;2024, 35(12): 110074. doi: 10.1016/j.cclet.2024.110074 shu

Synthesis and properties of tetraphenylethene cationic cyclophanes based on o-carborane skeleton

Rongjian Chen ^a ,
Jiahui Liu ^a ,
Caixia Lin ^{a, *,} ,
Yuanming Li ^a ,
Yanhou Geng ^{b, c, *,} ,
Yaofeng Yuan ^{a, *,}

a.
Key Laboratory of Molecule Synthesis and Function Discovery (Fujian Province University), Department of Chemistry, Fuzhou University, Fuzhou 350108, China
b.
School of Materials Science and Engineering and Tianjin Key Laboratory of Molecular Optoelectronic Science, Tianjin University, Tianjin 300072, China
c.
Joint School of National University of Singapore and Tianjin University, International Campus of Tianjin University, Fuzhou 350207, China

lincaixia_fzu@fzu.edu.cn

yanhou.geng@tju.edu.cn

yaofeng_yuan@fzu.edu.cn

Received Date: 18 February 2024
Revised Date: 22 May 2024
Accepted Date: 30 May 2024
Available Online: 31 May 2024

Figures(7)

Two o-carborane based tetraphenylethene (TPE) cationic cyclophanes O1·4PF₆ and O2·4PF₆ were synthesized through an S_N2 reaction. Their structures were confirmed both possessing Z-shaped cavities in single crystal analysis. The optical properties of these macrocycles were systematically investigated using UV–vis spectroscopy and fluorescence techniques. It is worth noting that the introduction of a methoxy group to the TPE unit enables the synthesis of a near-infrared-emitting macrocycle O2·4PF₆. The recognition behaviors of these two macrocycles towards nucleotides were investigated using various techniques including fluorescence titration, UV–vis titration, and transmission electron microscopy (TEM). Interestingly, these cyclophanes exhibited aggregation-induced emission (AIE) effects in water or under the induction of nucleotides.
- o-Carborane,
- Tetraphenylethene,
- Cationic cyclophanes,
- Nucleotides,
- AIE effect
1. [1]
  S.N. Lei, H. Xiao, Y. Zeng, et al., Angew. Chem. Int. Ed. 59 (2020) 10059–10065. doi: 10.1002/anie.201913340
2. [2]
  F. Yang, Y. Li, R. Li, et al., Org. Chem. Front. 9 (2022) 2902–2909. doi: 10.1039/D2QO00443G
3. [3]
  F. Yang, M. Zhen, S. Wang, et al., Chin. Chem. Lett. 33 (2022) 5088–5091. doi: 10.1016/j.cclet.2022.03.123
4. [4]
  X.-Y. Chen, H. Chen, J.Fraser Stoddart, Angew. Chem. Int. Ed. 62 (2023) e202211387. doi: 10.1002/anie.202211387
5. [5]
  B. Odell, M.V. Reddington, A.M.Z. Slawin, et al., Angew. Chem. Int. Ed. 27 (1988) 1547–1550. doi: 10.1002/anie.198815471
6. [6]
  W. Geuder, S. Hünig, A. Suchy, Angew. Chem. Int. Ed. 22 (1983) 489–490. doi: 10.1002/anie.198304891
7. [7]
  Y. Wang, J. Sun, Z. Liu, et al., Angew. Chem. Int. Ed. 55 (2016) 12387–12392. doi: 10.1002/anie.201605454
8. [8]
  Y. Lu, D. Liu, Y.J. Lin, et al., J. Am. Chem. Soc. 143 (2021) 12404–12411. doi: 10.1021/jacs.1c06689
9. [9]
  A. Garci, A.H.G. David, L.Le Bras, et al., J. Am. Chem. Soc. 144 (2022) 23551–23559. doi: 10.1021/jacs.2c10591
10. [10]
  J.C. Barnes, M. Jurícek, N.L. Strutt, et al., J. Am. Chem. Soc. 135 (2013) 183–192. ˇ doi: 10.1021/ja307360n
11. [11]
  I. Neira, A. Blanco-Gómez, J.M. Quintela, et al., Acc. Chem. Res. 53 (2020) 2336–2346. doi: 10.1021/acs.accounts.0c00445
12. [12]
  H. Chen, S. Hou, Q. Wu, et al., Matter 4 (2021) 3662–3676. doi: 10.1016/j.matt.2021.08.016
13. [13]
  Y. Li, Y. Dong, L. Cheng, et al., J. Am. Chem. Soc. 141 (2019) 8412–8415. doi: 10.1021/jacs.9b02617
14. [14]
  Y. Li, N. Li, G. Li, et al., J. Am. Chem. Soc. 145 (2023) 9118–9128. doi: 10.1021/jacs.3c00800
15. [15]
  X. Dong, X. Dai, G. Li, et al., Adv. Sci. 9 (2022) 2201962. doi: 10.1002/advs.202201962
16. [16]
  F. Yang, R. Li, W. Wei, et al., Angew. Chem. Int. Ed. 61 (2022) e202202491. doi: 10.1002/anie.202202491
17. [17]
  L. Bian, Y. Liang, Z. Liu, ACS Appl. Nano Mater. 5 (2022) 13940–13958. doi: 10.1021/acsanm.2c01250
18. [18]
  J. Zhang, W. Kang, X.D. Xu, Org. Chem. Front. 10 (2023) 6225–6239. doi: 10.1039/D3QO01426F
19. [19]
  H.T. Feng, Y.X. Yuan, J.B. Xiong, et al., Chem. Soc. Rev. 47 (2018) 7452–7476. doi: 10.1039/C8CS00444G
20. [20]
  L. Wang, Z. Guo, L. Cheng, et al., Dye. Pigm. 216 (2023) 111364. doi: 10.1016/j.dyepig.2023.111364
21. [21]
  L. Cheng, H. Zhang, Y. Dong, et al., Chem. Commun. 55 (2019) 2372–2375. doi: 10.1039/C9CC00599D
22. [22]
  C. Qin, Y. Li, Q. Li, et al., Chin. Chem. Lett. 32 (2021) 3531–3534. doi: 10.1016/j.cclet.2021.05.006
23. [23]
  H. Zhang, L. Cheng, H. Nian, et al., Chem. Commun. 57 (2021) 3135–3138. doi: 10.1039/D1CC00303H
24. [24]
  H. Duan, F. Cao, M. Zhang, et al., Chin. Chem. Lett. 33 (2022) 2459–2463. doi: 10.1016/j.cclet.2021.11.010
25. [25]
  J.B. Xiong, D.D. Ban, Y.J. Zhou, et al., RSC Adv. 12 (2022) 6876–6880. doi: 10.1039/D2RA00293K
26. [26]
  J.H. Wang, J.B. Xiong, X. Zhang, et al., RSC Adv. 5 (2015) 60096–60100. doi: 10.1039/C5RA09721E
27. [27]
  S.N. Lei, H. Cong, Chin. Chem. Lett. 33 (2022) 1493–1496. doi: 10.1016/j.cclet.2021.08.068
28. [28]
  H. Duan, T. Yang, Q. Li, et al., Chin. Chem. Lett. 35 (2024) 108878. doi: 10.1016/j.cclet.2023.108878
29. [29]
  R. Núñez, M. Tarrés, A. Ferrer-Ugalde, et al., Chem. Rev. 116 (2016) 14307–14378. doi: 10.1021/acs.chemrev.6b00198
30. [30]
  X. Yang, C.B. Knobler, M.F. Hawthorne, Angew. Chem. Int. Ed. 30 (1991) 1507–1508. doi: 10.1002/anie.199115071
31. [31]
  R.N. Grimes, Angew. Chem. Int. Ed. 32 (1993) 1289–1290. doi: 10.1002/anie.199312891
32. [32]
  I.T. Chizhevsky, S.E. Johnson, C.B. Knobler, et al., J. Am. Chem. Soc. 115 (1993) 6981–6982. doi: 10.1021/ja00068a069
33. [33]
  W. Jiang, I.T. Chizhevsky, M.D. Mortimer, et al., Inorg. Chem. 35 (1996) 5417–5426. doi: 10.1021/ic960354k
34. [34]
  C. Viñas, R. Núñez, F. Teixidor, Large molecules containing icosahedral boron clusters designed for potential applications, Boron Science, N.S. Hosmane, CRC Press, New York, 2012, pp. 701–731.
35. [35]
  P.F. Cui, X.R. Liu, G.X. Jin, J. Am. Chem. Soc. 145 (2023) 19440–19457. doi: 10.1021/jacs.3c05563
36. [36]
  S.T. Guo, P.F. Cui, X.R. Liu, et al., J. Am. Chem. Soc. 144 (2022) 22221–22228. doi: 10.1021/jacs.2c10201
37. [37]
  P.F. Cui, X.R. Liu, Y.J. Lin, et al., J. Am. Chem. Soc. 144 (2022) 6558–6565. doi: 10.1021/jacs.2c01668
38. [38]
  P.F. Cui, Y.J. Lin, Z.H. Li, et al., J. Am. Chem. Soc. 142 (2020) 8532–8538. doi: 10.1021/jacs.0c03176
39. [39]
  M. Zhu, Q. Zhou, H. Cheng, et al., Angew. Chem. Int. Ed. 62 (2023) e202213470. doi: 10.1002/anie.202213470
40. [40]
  Q. Qu, M. Fu, C. Lin, et al., Org. Chem. Front. 10 (2023) 3293–3299. doi: 10.1039/D3QO00487B
41. [41]
  A.H.G. David, A. Garci, S. Abid, et al., J. Am. Chem. Soc. 145 (2023) 9182–9190. doi: 10.1021/jacs.3c01244
42. [42]
  X. Chi, J. Tian, D. Luo, et al., Molecules 26 (2021) 2426. doi: 10.3390/molecules26092426
43. [43]
  A. Garci, Y. Beldjoudi, M.S. Kodaimati, et al., J. Am. Chem. Soc. 142 (2020) 7956–7967. doi: 10.1021/jacs.0c02128
44. [44]
  A. Garci, J.A. Weber, R.M. Young, et al., Nat. Catal. 5 (2022) 524–533. doi: 10.1038/s41929-022-00799-y
45. [45]
  W. Liu, Y. Tan, L.O. Jones, et al., J. Am. Chem. Soc. 143 (2021) 15688–15700. doi: 10.1021/jacs.1c06333
46. [46]
  Q.S. Fang, L. Chen, Q.Y. Liu, Chin. Chem. Lett. 28 (2017) 1013–1017. doi: 10.1016/j.cclet.2016.12.002
47. [47]
  Y. Sha, Z. Zhou, M. Zhu, et al., Angew. Chem. Int. Ed. 61 (2022) e202203169. doi: 10.1002/anie.202203169
48. [48]
  G. Yin, Y. Li, S. Li, et al., Dye. Pigments 198 (2022) 110013. doi: 10.1016/j.dyepig.2021.110013
49. [49]
  Y. Yue, F. Huo, F. Cheng, et al., Chem. Soc. Rev. 48 (2019) 4155–4177. doi: 10.1039/C8CS01006D
50. [50]
  Q.Y. Cao, L.X. Huang, S. Koo, et al., Sens. Actuator. B: Chem. 368 (2022) 132091. doi: 10.1016/j.snb.2022.132091
51. [51]
  B.S. Morozov, A.S. Oshchepkov, I. Klemt, et al., JACS Au 3 (2023) 964–977. doi: 10.1021/jacsau.2c00658
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