Skip to main content
SpringerLink
Log in

Shape-persistent macrocycles: efficient extraction towards lanthanide and actinide elements

  • Original Article
  • Published:
Journal of Inclusion Phenomena and Macrocyclic Chemistry Aims and scope Submit manuscript

Abstract

The extraction of three shape-persistent aromatic oligoamide macrocycles (cycloaramides) bearing either apolar or polar side chains at the periphery of the rings has been investigated towards some representative lanthanide and actinide ions, and alkali metal ions. The results from the liquid–liquid extraction of lanthanide and thorium ions from aqueous solutions into dichloromethane revealed remarkably high extractability of up to 99% and selectivity over alkali metal cations. The stoichiometry of the complex formed between the macrocycle and Eu3+ or Th4+ was determined to be 1:1.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Scheme 2
Fig. 1
Fig. 2
Fig. 3

Similar content being viewed by others

References

  1. Gong, B.: Hollow crescents, helices and macrocycles from enforced folding and folding-assisted macrocyclization. Acc. Chem. Res. 41, 1376–1386 (2008)

    Article  CAS  Google Scholar 

  2. Helsel, A.J., Brown, A.L., Yamato, K., Feng, W., Yuan, L.H., Clements, A., Harding, S.V., Szabo, G., Shao, Z.F., Gong, B.: Highly conducting transmembrane pores formed by aromatic oligoamide macrocycles. J. Am. Chem. Soc. 130, 15784–15785 (2008)

    Article  CAS  Google Scholar 

  3. Berni, E., Dolain, C., Kauffmann, B., Léger, J.-M., Zhan, C.L., Huc, I.: Expanding the registry of aromatic amide foldamers: folding, photochemistry and assembly using diaza-anthracene units. J. Org. Chem. 73, 2687–2694 (2008)

    Article  CAS  Google Scholar 

  4. Zhu, Y.Y., Li, C., Li, G.Y., Jiang, X.K., Li, Z.T.: Hydrogen bonded aryl amide macrocycles: synthesis, single-crystal structures, and aromatic interactions with fullerenes. J. Org. Chem. 73, 1745–1751 (2007)

    Article  Google Scholar 

  5. Gatti, F.G., León, S., Wong, J.K.Y., Bottari, G., Altieri, A., Morales, M.A.F., Teat, S.J., Frochot, C., Leigh, D.A., Brouwer, A.M., Zerbetto, F.: Photoisomerization of a rotaxane hydrogen bonding template: light-induced acceleration of a large amplitude rotational motion. Proc. Natl. Acad. Sci. USA. 100, 10–14 (2003)

    Article  CAS  Google Scholar 

  6. Masu, H., Okamoto, T., Kato, T., Katagiri, K., Tominaga, M., Goda, H., Takayanagi, H., Azumaya, I.: Construction of macrocyclic structure using conformational properties of secondary and tertiary aromatic amides. Tetrahedron Lett. 47, 803–807 (2006)

    Article  CAS  Google Scholar 

  7. Jiang, H., Léger, J.-M., Guionneau, P., Huc, I.: Strained aromatic oligoamide macrocycles as new molecular clips. Org. Lett. 6, 2985–2988 (2004)

    Article  CAS  Google Scholar 

  8. Kim, Y.H., Calabrese, J., McEwen, C.: CaCl3 − or Ca2Cl4 complexing cyclic aromatic amide. Template effect on cyclization. J. Am. Chem. Soc. 118, 1545–1546 (1996)

    Article  CAS  Google Scholar 

  9. Qin, B., Ren, C.L., Ye, R.J., Sun, C., Chiad, K., Chen, X.J., Li, Z., Xue, F., Su, H.B., Chass, G.A., Zeng, H.Q.: Persistently folded circular aromatic amide pentamers containing modularly tunable cation-binding cavities with high ion selectivity. J. Am. Chem. Soc. 132, 9564–9566 (2010)

    Article  CAS  Google Scholar 

  10. Yuan, L.H., Zeng, H.Q., Yamato, K., Sanford, A.R., Feng, W., Atreya, H., Sukumaran, D.K., Szyperski, T., Gong, B.: Helical aromatic oligoamides: reliable, readily predictable folding from the combination of rigidified structural motifs. J. Am. Chem. Soc. 126, 16528–16537 (2004)

    Article  CAS  Google Scholar 

  11. Feng, W., Yamato, K., Yang, L.Q., Ferguson, J., Zhong, L.J., Zou, S.L., Yuan, L.H., Zeng, X.C., Gong, B.: Efficient kinetic macrocyclization. J. Am. Chem. Soc. 131, 2629–2637 (2009)

    Article  CAS  Google Scholar 

  12. Zang, L., Che, Y., Moore, J.S.: One-dimensional self-assembly of planar π-conjugated molecules: adaptable building blocks for organic nanodevices. Acc. Chem. Res. 12, 1596–1608 (2008)

    Article  Google Scholar 

  13. He, L., An, Y., Yuan, L.H., Feng, W., Li, M.F., Zhang, D.C., Yamato, K., Zheng, C., Zeng, X.C., Gong, B.: Shape-persistent macrocyclic aromatic tetrasulfonamides: molecules with nanosized cavities and their nanotubular assemblies in solid state. Proc. Natl. Acad. Sci. USA. 103, 10850–10855 (2006)

    Article  CAS  Google Scholar 

  14. Höger, S.: Shape-persistent macrocycles: from molecules to materials. Chem. Eur. J. 10, 1320–1329 (2004)

    Article  Google Scholar 

  15. Sanford, A.R., Yuan, L.H., Feng, W., Yamato, K., Flowers, R.A., Gong, B.: Cyclic aromatic oligoamides as highly selective receptors for the guanidinium ion. Chem. Commun. 37, 4720–4722 (2005)

    Article  Google Scholar 

  16. Zou, S.L., He, Y.Z., Yang, Y.A., Zhao, Y., Yuan, L.H., Feng, W., Yamato, K., Gong, B.: Improving the efficiency of forming ‘unfavorable’ products: eight-residue macrocycles from folded aromatic oligoamide precursors. Synlett 9, 1437–1440 (2009)

    Google Scholar 

  17. Yang, L.Q., Zhong, L.J., Yamato, K., Zhang, X.H., Feng, W., Deng, P.C., Yuan, L.H., Zeng, X.C., Gong, B.: Aromatic oligoamide macrocycles from biomolecular coupling of folded oligomeric precursors. New J. Chem. 33, 729–733 (2009)

    Article  CAS  Google Scholar 

  18. Tsukanov, A.V., Dubonosov, A.D., Bren, V.A., Minkin, V.I.: Organic chemosensors with crown-ether groups (review). Chem. Heterocycl. Compd. 44, 899–923 (2008)

    Article  CAS  Google Scholar 

  19. Gokel, G.W., Leevy, W.M., Weber, M.E.: Crown ethers: sensors for ions and molecular scaffolds for materials and biological models. Chem. Rev. 104, 2723–2750 (2004)

    Article  CAS  Google Scholar 

  20. Liu, Y., Han, B.H., Chen, Y.T.: The complexation thermodynamics of light lanthanides by crown ethers. Coord. Chem. Rev. 200, 53–73 (2000)

    Article  Google Scholar 

  21. Schneider, H.J., Yatsimirsky, A.K.: Selectivity in supramolecular host–guest complexes. Chem. Soc. Rev. 37, 263–277 (2008)

    Article  CAS  Google Scholar 

  22. Mutihac, R.-C., Buschmann, H.-J., Schollmeyer, E.: Influence of polar solvents upon the complex formation of 18-crown-6 with cations in chloroform. J. Incl. Phenom. Macrocycl. Chem. 68, 411–416 (2010)

    Article  CAS  Google Scholar 

  23. Merck, E., Méthodes d’analyses complexométriques par les Titriplex, 3ème ed, Darmstadt, Germany

  24. Maria, K., Françoise, A.N., Véronique, H.B., Igor, S., Vitaly, K.: Novel phosphorylated calixarenes for the recognition of f-elements. J. Incl. Phenom. Macrocycl. Chem. 66, 113–123 (2010)

    Article  Google Scholar 

  25. Yuan, L.H., Sanford, A.R., Feng, W., Zhang, A.M., Ferguson, J.S., Yamato, K., Zhu, J., Zeng, H.Q., Gong, B.: Synthesis of crescent aromatic oligoamides. J. Org. Chem. 70, 10660–10669 (2005)

    Article  CAS  Google Scholar 

  26. Hirose, K.: A practical guide for the determination of binding constants. J. Incl. Phenom. Macrocycl. Chem. 39, 193–209 (2001)

    Article  CAS  Google Scholar 

  27. Bartsch, R.A., Yang, I.W., Jeon, E.G., Walkowiak, W., Charewicz, W.A.: Selective transport of alkali metal cations in solvent extraction by proton-ionizable dibenzo-crown ethers. J. Coord. Chem. 27, 75–85 (1992)

    Article  CAS  Google Scholar 

  28. Park, C., Chun, S., Bartsch, R.A.: Effect of conformation on metal ion extraction by calix[4]arene dicarboxylic acids. J. Incl. Phenom. Macrocycl. Chem. 66, 95–105 (2010)

    Article  CAS  Google Scholar 

  29. Peters, M.W., Werner, E.J., Scott, M.J.: Enhanced selectivity for actinides over lanthanides with CMPO ligands secured to a C3-symmetric triphenoxymethane platform. Inorg. Chem. 41, 1707–1716 (2002)

    Article  CAS  Google Scholar 

  30. Arnaud-Neu, F., Browne, J.K., Byrne, D., Marrs, D.J., McKervey, M.A., Hagan, P.O., Schwing-Weill, M.J., Walker, A.: Extraction and complexation of alkali, alkaline earth, and f-element cations by calixaryl phosphine oxides. Chem. Eur. J. 5, 175–186 (1999)

    Article  CAS  Google Scholar 

  31. Pedersen, C.: New macrocyclic polyethers. J. Am. Chem. Soc. 92, 391–394 (1970)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work is supported by the National Natural Science Foundation (20774059, 20672078) and the Doctoral Program of the Ministry of Education of China (20090181110047). Analytical & Testing Center of Sichuan University is acknowledged for technical assistance of NMR experiments.

Author information

Authors and Affiliations

  1. College of Chemistry, Key Laboratory for Radiation Physics and Technology of Ministry of Education, Institute of Nuclear Science and Technology, Sichuan University, Chengdu, 610064, China

    Lijian Zhong, Long Chen, Wen Feng, Shuliang Zou, Yuanyou Yang, Ning Liu & Lihua Yuan

Authors
  1. Lijian Zhong
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Long Chen
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Wen Feng
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Shuliang Zou
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Yuanyou Yang
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Ning Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Lihua Yuan
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Lihua Yuan.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOC 919 kb)

Rights and permissions

Reprints and permissions

About this article

Cite this article

Zhong, L., Chen, L., Feng, W. et al. Shape-persistent macrocycles: efficient extraction towards lanthanide and actinide elements. J Incl Phenom Macrocycl Chem 72, 367–373 (2012). https://doi.org/10.1007/s10847-011-9991-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10847-011-9991-9

Keywords

Search

Navigation