Citation: Dong Fang, Xiaofan Yang, Fengxin Gao, Chengliang Xiao. Straightforward and versatile construction of phenanthroline-derived diamide ligands for f-block element extraction[J]. Chinese Chemical Letters, ;2026, 37(1): 111252. doi: 10.1016/j.cclet.2025.111252 shu

Straightforward and versatile construction of phenanthroline-derived diamide ligands for f-block element extraction

Dong Fang ^{a, b} ,
Xiaofan Yang ^a ,
Fengxin Gao ^a ,
Chengliang Xiao ^{a, b, *,}

a.
College of Chemical and Biological Engineering, Zhejiang University, Hangzhou 310058, China
b.
Institute of Zhejiang University-Quzhou, Quzhou 324000, China

xiaoc@zju.edu.cn

Received Date: 23 August 2024
Revised Date: 24 March 2025
Accepted Date: 22 April 2025
Available Online: 24 April 2025

Figures(4)

As an important class of phenanthroline derivatives containing soft N and hard O donor atoms, the laborious syntheses of unsymmetrical 1, 10-phenanthroline-derived diamide ligands (DAPhen) have hindered its extensive study. In this work, we first report a convenient synthetic method for the construction of DAPhen using Friedländer reaction by two facile steps (vs. previous 12 steps). A variety of DAPhen ligands are readily available, especially unsymmetrical ones, which give us a platform to systematically study the substituent effect on f-block elements extraction performance. The performance of unsymmetrical extractants is experimentally confirmed to falls between that of their corresponding symmetrical extractants by extracting UO₂²⁺ as the representative f-block element. This work provides a direct and versatile method to synthesize symmetrical and unsymmetrical DAPhen, which paves way for the investigations on their coordination properties with metal ions and other applications.
- Phenanthroline diamide ligand,
- Friedländer reaction,
- Unsymmetrical,
- Symmetrical,
- Solvent extraction
1. [1]
  P. Chen, H. Zheng, H. Jiang, et al., Chin. Chem. Lett. 33 (2022) 907–911. doi: 10.23919/eusipco55093.2022.9909729
2. [2]
  D. Wu, H. Pang, G. Yin, Chin. Chem. Lett. 34 (2023) 108087. doi: 10.1016/j.cclet.2022.108087
3. [3]
  G.M. Cockrell, G. Zhang, D.G. VanDerveer, et al., J. Am. Chem. Soc. 130 (2008) 1420–1430. doi: 10.1021/ja077141m
4. [4]
  A. Bencini, V. Lippolis, Coord. Chem. Rev. 254 (2010) 2096–2180. doi: 10.1016/j.ccr.2010.04.008
5. [5]
  M. Qian, D. Zhang, H. Qi, et al., Chin. Chem. Lett. 34 (2023) 107336. doi: 10.1016/j.cclet.2022.03.059
6. [6]
  A. Leoncini, J. Huskens, W. Verboom, Chem. Soc. Rev. 46 (2017) 7229–7273. doi: 10.1039/C7CS00574A
7. [7]
  S.V. Gutorova, P.I. Matveev, P.S. Lemport, et al., Inorg. Chem. 61 (2021) 384–398.
8. [8]
  X. Yu, Y. Hu, C. Guo, et al., Supramol. Mater. 1 (2022) 100017.
9. [9]
  C.L. Xiao, C.Z. Wang, L.Y. Yuan, et al., Inorg. Chem. 53 (2014) 1712–1720. doi: 10.1021/ic402784c
10. [10]
  L. Xu, X. Yang, A. Zhang, C. Xu, C. Xiao, Coord. Chem. Rev. 496 (2023) 215404. doi: 10.1016/j.ccr.2023.215404
11. [11]
  S. Jansone-Popova, A.S. Ivanov, V.S. Bryantsev, et al., Inorg. Chem. 56 (2017) 5911–5917. doi: 10.1021/acs.inorgchem.7b00555
12. [12]
  M. Galletta, S. Scaravaggi, E. Macerata, et al., Dalton. Trans. 42 (2013) 16930–16938. doi: 10.1039/c3dt52104d
13. [13]
  T. Xiu, S. Zhang, P. Ren, et al., Chin. Chem. Lett. 34 (2023) 108440. doi: 10.1016/j.cclet.2023.108440
14. [14]
  A.C. Edwards, A. Geist, U. Müllich, et al., Chem. Commun. 53 (2017) 8160–8163. doi: 10.1039/C7CC03903D
15. [15]
  L. Duan, J. Fan, D. Tian, et al., Colloids Surf. A 647 (2022) 129089. doi: 10.1016/j.colsurfa.2022.129089
16. [16]
  D.T. Mooney, B.D.T. Donkin, N. Demirel, P.R. Moore, A.L. Lee, J. Org. Chem. 86 (2021) 17282–17293. doi: 10.1021/acs.joc.1c02425
17. [17]
  S. Wang, X. Yang, L. Xu, et al., Ind. Eng. Chem. Res. 62 (2023) 15613–15624. doi: 10.1021/acs.iecr.3c02101
18. [18]
  S. Wang, X. Yang, Y. Liu, et al., Inorg. Chem. 63 (2024) 3063–3074. doi: 10.1021/acs.inorgchem.3c03997
19. [19]
  R. Meng, L. Xu, X. Yang, et al., Inorg. Chem. 60 (2021) 8754–8764. doi: 10.1021/acs.inorgchem.1c00715
20. [20]
  Y.A. Ustynyuk, N.E. Borisova, V.A. Babain, et al., Chem. Commun. 51 (2015) 7466–7469. doi: 10.1039/C5CC01620G
21. [21]
  H. Wang, P. Gao, T. Cui, et al., Dalton. Trans. 53 (2024) 601–611. doi: 10.1039/d3dt03194b
22. [22]
  X. Zhang, L. Yuan, Z. Chai, W. Shi, Sci. Chin. Chem. 61 (2018) 1285–1292. doi: 10.1007/s11426-018-9227-1
23. [23]
  C.L. Xiao, Q.Y. Wu, C.Z. Wang, et al., Inorg. Chem. 53 (2014) 10846–10853. doi: 10.1021/ic500816z
24. [24]
  J. Marco-Contelles, E. Pérez-Mayoral, A. Samadi, M.D.C. Carreiras, E. Soriano, Chem. Rev. 109 (2009) 2652–2671. doi: 10.1021/cr800482c
25. [25]
  Y. Lu, Y. Jahng, Chin. J. Chem. 37 (2018) 221–225.
26. [26]
  D. Fang, X. Yang, J. Li, et al., Inorg. Chem. 63 (2024) 8171–8179. doi: 10.1021/acs.inorgchem.4c00395
27. [27]
  C.Y. Hung, T.L. Wang, Y. Jang, W.Y. Kim, R.H. Schmehl, R.P. Thummel, Inorg. Chem. 35 (1996) 5953–5956. doi: 10.1021/ic960409i
28. [28]
  E.C. Riesgo, X. Jin, R.P. Thummel, J. Org. Chem. 61 (1996) 3017–3022. doi: 10.1021/jo952164h
29. [29]
  B. Ma, T. Miao, Y. Sun, et al., Chem. Eur. J. 20 (2014) 9969–9978. doi: 10.1002/chem.201402709
30. [30]
  X. Yang, D. Fang, L. Chen, et al., JACS Au 4 (2024) 4744–4756. doi: 10.1021/jacsau.4c00684
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2. [2]
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