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Syntheses and crystal structures of two self-assembled dizinc(II) helicates with novel hydrazone linked polypyridyl ligands

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Abstract

The rationally designed polydentate ligands, L 1 and L 2, based on the pyridinyl moiety and the hydrazone fragment have been synthesized to coordinate zinc(II) ions. We utilize pyridine as a rigid core connecting two bipyridines as ligand building blocks with a hydrozone linker for the L 1. The L 2 has a reversed design in which a bipyridine was used as a hinging-available building block of the ligand core, connecting two pyridazine arms with a hydrazone linker. Two novel helical dizinc(II) complexes were obtained by the reaction of L 1 and L 2 with zinc(II) perchlorate in acetonitrile. The structures of both helicates were confirmed by X-ray diffractometry. Single-stranded helicate Zn 2 L 1 contains two zinc ions bridged by an oxygen atom. Except for the L 2 ligand, no other bridging species were found between the two zinc ions in the double-stranded helicate Zn 2 L 2 2 . The self-assembling process of helicate Zn 2 L 1 in solution state was studied by UV–Vis spectrometric titration experiments. The stepwise formation constants imply a slightly positive cooperative behavior for the formation of helicates.

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References

  1. U. Koert, M.M. Harding, J.-M. Lehn, Nature 346, 339–342 (1990)

    Article  CAS  Google Scholar 

  2. J.S. Lindsey, New J. Chem. 15, 153–180 (1991)

    CAS  Google Scholar 

  3. J.-M. Lehn, Supramolecular Chemistry-Concepts and Perspectives (VCH, Weinheim, 1995)

    Book  Google Scholar 

  4. C. Piguet, C. Edder, S. Rigault, G. Bernardinelli, J.-C. G. Bünzli, G. Hopfgartner, J. Chem. Soc., Dalton Trans. 22, 3999-4006 (2000)

    Article  Google Scholar 

  5. R. Ziessel, Coord. Chem. Rev. 195, 201–217 (2001)

    Google Scholar 

  6. Y.-M. Legrand, A. Van Der Lee, M. Barboiu, Inorg. Chem. 46, 9540–9547 (2007)

    Article  CAS  Google Scholar 

  7. J.-M. Lehn, Chem. Soc. Rev. 36, 151–160 (2007)

    Article  CAS  Google Scholar 

  8. J.P. Sauvage, Transition Metals in Supramolecular Chemistry (Wiley, New Yoek, 2008)

    Google Scholar 

  9. E. Yashima, K. Maeda, Y. Furusho, Acc. Chem. Res. 41, 1166–1180 (2008)

    Article  CAS  Google Scholar 

  10. E. Yashima, K. Maeda, H. Iida, Y. Furusho, K. Nagai, Chem. Rev. 109, 6102–6211 (2009)

    Article  CAS  Google Scholar 

  11. D. Haldar, C. Schmuck, Chem. Soc. Rev. 38, 363–371 (2009)

    Article  CAS  Google Scholar 

  12. J.-M. Lehn, Angew. Chem. 100, 91–116 (1988)

    Article  CAS  Google Scholar 

  13. K. Zegelaar-Jaarsveld, G.A. Van DerMarel, J.H. Van Boom, Tetrahedron 48, 10013–10148 (1992)

    Article  Google Scholar 

  14. P.T. Corbett, J. Leclaire, L. Vial, K.R. West, J.-L. Wietor, J.K.M. Sanders, S. Otto, Chem. Rev. 106, 3652–3711 (2006)

    Article  CAS  Google Scholar 

  15. M. Nishijima, J.-W. Chang, C. Yang, G. Fukuhara, T. Mori, Y. Inoue, Res. Chem. Intermed. 39, 371–383 (2013)

    Article  CAS  Google Scholar 

  16. V. Amendola, L. Fabbrizzi, C. Mangano, P. Pallavicini, E. Roboli, M. Zema, Inorg. Chem. 39, 5803–5806 (2000)

    Article  CAS  Google Scholar 

  17. V. Amendola, L. Fabbrizzi, P. Pallavicini, E. Sartirana, A. Taglietti, Inorg. Chem. 42, 1632–1636 (2003)

    Article  CAS  Google Scholar 

  18. T. Ghosh, S. Pal, Inorg. Chim. Acta 363, 3632–3636 (2010)

    Article  CAS  Google Scholar 

  19. R.-F. Song, Y.-Y. Sun, J. Yang, X.-Y. Yang, J. Inorg. Organomet. Polym. 21, 237–243 (2011)

    Article  CAS  Google Scholar 

  20. M.T. Youinou, R. Ziessel, J.-M. Lehn, Inorg. Chem. 30, 2144–2148 (1991)

    Article  CAS  Google Scholar 

  21. A.-M. Stadler, N. Kyritsakas, G. Vaughan, J.-M. Lehn, Chem. Eur. J. 13, 59–68 (2007)

    Article  CAS  Google Scholar 

  22. F.A. Cotton, G. Wilkinson, Advanced Inorganic Chemistry (Wiley, New York, 1988)

    Google Scholar 

  23. D.S. Auld, Biometals 14, 271–313 (2001)

    Article  CAS  Google Scholar 

  24. J.M. Berg, Y. Shi, Science 271, 1081–1085 (1996)

    Article  CAS  Google Scholar 

  25. L.A. Finney, T.V. O’Halloran, Science 300, 931–936 (2003)

    Article  CAS  Google Scholar 

  26. N.C. Lim, H.C. Freake, C. Brückner, Chem. Eur. J. 11, 38–49 (2005)

    Article  Google Scholar 

  27. Y. Wu, J.-C. Liu, J. Cao, R.-Z. Li, N.-Z. Jin, Res. Chem. Intermed. (2014). doi:10.1007/s11164-014-1781-8

    Google Scholar 

  28. H.-C. Kao, Y.-C. Wang, W.-J. Wang, J. Chin. Chem. Soc. 57, 876–882 (2010)

    Article  Google Scholar 

  29. H.-C. Kao, Y.-C. Wang, W.-J. Wang, J. Chin. Chem. Soc. 59, 934–939 (2012)

    Article  CAS  Google Scholar 

  30. G.M. Sheldrick, SHELX-97, Programs for Crystal Structure Solution and Refinement (University of Göttingen, Göttingen, 1997)

    Google Scholar 

  31. SADABS. Version 2007/2. G. M. Sheldrick, (Bruker AXS Inc. Madison, Wisconsin, USA, 1997)

  32. R. Binstead, A. D. Zuberbuhler, SPECFIT Global Analysis System, 2.10 edn. (Spectrum Software Associates: Chapel Hill, NC 27515, 1998)

  33. E.R. Malinowski, D.G. Howery, Factor Analysis in Chemistry (Wiley, New York, 1980)

    Google Scholar 

  34. H. Gampp, M. Maeder, C.J. Meyer, A.D. Zuberbuhler, Talanta 23, 1133–1139 (1985)

    Article  Google Scholar 

  35. H. Gampp, M. Maeder, C.J. Meyer, A.D. Zuberbuhler, Talanta 33, 943–951 (1986)

    Article  CAS  Google Scholar 

  36. S. Anderson, E. C. Constable, K. R. Seddon, J. E. Turp, J. E. Baggott, M. J. Pilling, J. Chem. Soc., Dalton Trans. 11, 2247-2261 (1985)

    Article  Google Scholar 

  37. C. Piguet, B. Bocquet, A. Quattropani, J. Am. Chem. Soc. 114, 7440–7451 (1992)

    Article  CAS  Google Scholar 

  38. C. Piguet, B. Bocquet, A. Quattropani, J. Am. Chem. Soc. 116, 9092–9102 (1994)

    Article  CAS  Google Scholar 

  39. J. Hamacek, S. Blanc, M. Elhabiri, E. Leize, A.V. Dorsselaer, C. Piguet, A.M. Albrecht-Gary, J. Am. Chem. Soc. 125, 1541–1550 (2003)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work was financially supported by Tamkang University and the Ministry of Science and Technology (NSC 97-2113-M-032-006). The authors thank Mr. Pierre LaPorte for reading the article.

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Authors and Affiliations

  1. Department of Chemistry, Tamkang University, Tamsui, New Taipei City, 25137, Taiwan

    Hsien-Chang Kao, Yi-Chun Wang & Wen-Jwu Wang

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  1. Hsien-Chang Kao
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  2. Yi-Chun Wang
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  3. Wen-Jwu Wang
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Correspondence to Wen-Jwu Wang.

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Kao, HC., Wang, YC. & Wang, WJ. Syntheses and crystal structures of two self-assembled dizinc(II) helicates with novel hydrazone linked polypyridyl ligands. Res Chem Intermed 43, 3539–3552 (2017). https://doi.org/10.1007/s11164-016-2426-x

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  • DOI: https://doi.org/10.1007/s11164-016-2426-x

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