Citation: Xianchen Hu, Junli Yang, Fang Gao, Zhiyong Zhao, Simin Liu. Highly selective [4+4] cross-photodimerization of (4a-azonia)anthracenes driven by confinement of D-A hetero-guest pair in cucurbit[10]uril host[J]. Chinese Chemical Letters, ;2025, 36(3): 109967. doi: 10.1016/j.cclet.2024.109967 shu

Highly selective [4+4] cross-photodimerization of (4a-azonia)anthracenes driven by confinement of D-A hetero-guest pair in cucurbit[10]uril host

Xianchen Hu ^a ,
Junli Yang ^a ,
Fang Gao ^a ,
Zhiyong Zhao ^{a, b} ,
Simin Liu ^{a, b, *,}

a.
School of Chemistry and Chemical Engineering, Wuhan University of Science and Technology, Wuhan 430081, China
b.
The State Key Laboratory of Refractories and Metallurgy, Institute of Advanced Materials and Nanotechnology, Wuhan University of Science and Technology, Wuhan 430081, China

Received Date: 23 February 2024
Revised Date: 19 April 2024
Accepted Date: 5 May 2024
Available Online: 6 May 2024

Figures(4)

The cross-photodimerization often comes with the formation of undesired and competitive homo-photodimer as side products. Herein, we report a series of highly selective [4 + 4] cross-photodimerization between anthracene and 4a-azoniaanthracene derivatives within a cucurbit[10]uril (CB[10]) host in water. Heteroternary inclusion complexes were formed through encapsulation of donor (D1-D2, anthracene derivative) and acceptor (A1-A3, 4a-azoniaanthracene derivatives) pairs in CB[10]. In the presence of CB[10] (1.0 equiv.), the [4 + 4] cross-photodimerization between D1 and A1/A2/A3 efficiently gave a single racemic cross-photodimer. Furthermore, the cross-photodimerization between 9-substituted anthracene D2 and A1/A3 was catalyzed by CB[10] (0.1 equiv.) to quantitatively yield a cross-photodimer with high regioselectivity. Efficient formation of selective cross-photodimers could be attributed to the exclusive encapsulation of D-A hetero-guest pairs in CB[10] and the confinement effect of the CB[10] host cavity. Our study further proves host–guest complexation as a powerful strategy for cross-cycloaddition reactions with high efficiency.
- Supramolecular catalysis,
- Cross-photodimerization,
- Host-guest complexation,
- Charge-transfer interaction,
- Cucurbit[10]uril
1. [1]
  W. Liu, L. Guo, Y. Fan, et al., Chin. J. Org. Chem. 37 (2017) 543–554. doi: 10.6023/cjoc20161101
2. [2]
  X. Wang, W.G. Liu, L.T. Liu, et al., Org. Lett. 23 (2021) 5485–5490. doi: 10.1021/acs.orglett.1c01839
3. [3]
  W. Xu, X.D. Yang, X.B. Fan, et al., Angew. Chem. Int. Ed. 58 (2019) 3943– 3947. doi: 10.1002/anie.201814482
4. [4]
  W. Zhou, Y. Chen, Q. Yu, et al., Chem. Sci. 10 (2019) 3346–3352. doi: 10.1039/C9SC00026G
5. [5]
  H. Bouas-Laurent, A. Castellan, J.P. Desvergne, Pure Appl. Chem. 52 (1980) 2633–2648. doi: 10.1351/pac198052122633
6. [6]
  Y. Kawanami, H. Umehara, J.I. Mizoguchi, et al., J. Org. Chem. 78 (2013) 3073–3085. doi: 10.1021/jo302818w
7. [7]
  D. Bailey, N. Seifi, V.E. Williams, Dyes Pigments 89 (2011) 313–318. doi: 10.1016/j.dyepig.2010.05.016
8. [8]
  L. Wang, C. Su, Supramolecular Catalysts, World Scientific, Singapore, 2020.
9. [9]
  D.S. Dalal, D.R. Patil, Y.A. Tayade, Chem. Rec. 18 (2018) 1560–1582. doi: 10.1002/tcr.201800016
10. [10]
  P. Neri, J.L. Sessler, M.X. Wang, In Calixarenes and Beyond, Springer, 2016.
11. [11]
  Y. Xue, X. Hang, J. Ding, et al., Coord. Chem. Rev. 430 (2021) 213656. doi: 10.1016/j.ccr.2020.213656
12. [12]
  C. Wang, L. Xu, Z. Jia, et al., Chin. Chem. Lett. 35 (2024) 109075. doi: 10.1016/j.cclet.2023.109075
13. [13]
  M. Yoshizawa, M. Tamura, M. Fujita, Science 312 (2006) 251–254. doi: 10.1126/science.1124985
14. [14]
  J.S. Wang, K. Wu, C. Yin, et al., Nat. Commun. 11 (2020) 4675. doi: 10.1038/s41467-020-18487-5
15. [15]
  Y. Jiao, X.Y. Chen, J.F. Stoddart, Chem 8 (2022) 414–438. doi: 10.1016/j.chempr.2021.12.012
16. [16]
  K. Wang, J.H. Jordan, X.Y. Hu, et al., Angew. Chem. Int. Ed. 59 (2020) 13712–13721. doi: 10.1002/anie.202000045
17. [17]
  S. Yamada, Chem. Rev. 118 (2018) 11353–11432. doi: 10.1021/acs.chemrev.8b00377
18. [18]
  M. Rao, W. Wu, C. Yang, Green Synth. Catal. 2 (2021) 131–144. doi: 10.1016/j.gresc.2021.03.005
19. [19]
  S.J. Barrow, S. Kasera, M.J. Rowland, et al., Chem. Rev. 115 (2015) 12320– 12406. doi: 10.1021/acs.chemrev.5b00341
20. [20]
  X.L. Ni, X. Xiao, H. Cong, et al., Acc. Chem. Res. 47 (2014) 1386–1395. doi: 10.1021/ar5000133
21. [21]
  K.I. Assaf, W.M. Nau, Chem. Soc. Rev. 44 (2015) 394–418. doi: 10.1039/C4CS00273C
22. [22]
  B. Tang, J. Zhao, J.F. Xu, et al., Chem. Eur. J. 26 (2020) 15446–15460. doi: 10.1002/chem.202003897
23. [23]
  H. Barbero, E. Masson, In: K. Kim (Ed.), Cucurbiturils as reaction vessels, Cucurbiturils and Related Macrocycles, Royal Society of Chemistry, 2019, pp. 86– 120.
24. [24]
  X. Yang, F. Liu, Z. Zhao, et al., Chin. Chem. Lett. 29 (2018) 1560–1566. doi: 10.1016/j.cclet.2018.01.032
25. [25]
  Y.L. Lu, X.D. Zhang, Y.H. Qin, et al., Chem 9 (2023) 2144–2160. doi: 10.1016/j.chempr.2023.03.019
26. [26]
  W. Gong, X. Yang, P.Y. Zavalij, et al., Chem. Eur. J. 22 (2016) 17612–17618. doi: 10.1002/chem.201604149
27. [27]
  J. Yang, X. Hu, M. Fan, et al., Org. Chem. Front. 10 (2023) 422–429. doi: 10.1039/D2QO01831D
28. [28]
  X. Hu, F. Liu, X. Zhang, et al., Chem. Sci. 11 (2020) 4779–4785. doi: 10.1039/D0SC00409J
29. [29]
  H. Li, X. Hu, F. Liu, et al., Chin. Chem. Lett. 33 (2022) 5124–5127. doi: 10.1016/j.cclet.2022.04.030
30. [30]
  S.A. Stratford, M. Arhangelskis, D.K. Bučar, et al., CrystEngComm 16 (2014) 10830–10836. doi: 10.1039/C4CE01622J
31. [31]
  H. Ihmels, J. Luo, J. Photochem. Photobiol. A: Chem. 200 (2008) 3–9. doi: 10.1016/j.jphotochem.2008.04.008
32. [32]
  T. Wolff, C. Lehnberger, D. Scheller, Heterocycles 45 (1997) 2033–2039. doi: 10.3987/COM-97-7891
33. [33]
  D. Sun, Y. Wu, X. Han, et al., Nat. Commun. 14 (2023) 4190. doi: 10.1038/s41467-023-39956-7
34. [34]
  X. Wei, W. Wu, R. Matsushita, et al., J. Am. Chem. Soc. 140 (2018) 3959– 3974. doi: 10.1021/jacs.7b12085
35. [35]
  S. Liu, P.Y. Zavalij, L. Isaacs, J. Am. Chem. Soc. 127 (2005) 16798–16799. doi: 10.1021/ja056287n
36. [36]
  N. Hickey, B. Medagli, A. Pedrini, et al., Cryst. Growth Des. 21 (2021) 3650–3655. doi: 10.1021/acs.cgd.1c00463
37. [37]
  J. Gemen, J.R. Church, T.P. Ruoko, et al., Science 381 (2023) 1357–1363. doi: 10.1126/science.adh9059
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2. [2]
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7. [7]
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