Skip to main content
Log in

Synthesis of a linearly linked triscalixarene consisting of calix[4]arene units with combined axial chirality and inherent chirality

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

Abstract

A linearly linked triscalix[4]arene, in which each calix[4]arene unit possesses both axial chirality and inherent chirality, was synthesized by repeated use of two stereoselective Williamson etherification on calix[4]arene. In the crystal lattice of the biscalix[4]arene intermediate, there are interesting alternate layers of biscalixarene molecules and solvent molecules in the ab plane.

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

Access this article

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

Instant access to the full article PDF.

Scheme 1
Scheme 2
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5

Similar content being viewed by others

References

  1. Sameni, S., Jeunesse, C., Matt, D., Harrowfield, J.: Chem. Soc. Rev. 38, 2117–2146 (2009)

    Article  CAS  Google Scholar 

  2. Kim, J.S., Lee, S.Y., Yoon, J., Vicens, J.: Chem. Commun. 32 4791–4802 (2009)

    Article  Google Scholar 

  3. Szemes, F., M.G.B. Drew, Beer, P.D.: Chem. Commun. 11, 1228–1229 (2002)

    Article  Google Scholar 

  4. Lambert, J.B., Kang, S.-H., Ma, K., Liu, C., Condie, A.G.: J. Org. Chem. 74, 2527–2532 (2009)

    Article  CAS  Google Scholar 

  5. Galán, H., Murillo, M.T., Quesada, R., Escudero-Adán, E.C., Benet-Bucholz, J., Prados, P., de Mendoza, J.: Chem. Commun. 46, 1044–1046 (2010)

    Article  Google Scholar 

  6. Ben Othman, A., Lee, J.W., Wu, J.-S., Kim, J.S., Abidi, R., Thuéry, P., Strub, J.-M., Dorssaeler, A.V., Vicens, J.: J. Org. Chem. 72, 7634–7640 (2007)

    Article  CAS  Google Scholar 

  7. Lalor, R., DiGesso, J.L., Mueller, A., Matthews, S. E.: Chem. Commun. 46, 4907–4909, (2007)

    Article  Google Scholar 

  8. Lalor, R., Gunning, A.P., Morris, V.J., Matthews, S. E.: Chem. Commun. 46, 8665–8667 (2010)

    Article  CAS  Google Scholar 

  9. Liu, J.-M., Zheng, Y.-S., Zheng, Q.-Y., Xie, J., Wang, M.-X., Huang, Z.-T.: Tetrahedron 58, 3729–3736 (2002)

    Article  CAS  Google Scholar 

  10. Lhoták, P., Kawaguchi, M., Ikeda, A., S. Shinkai.: Tetrahedron 52, 12399–12408 (1996)

    Article  Google Scholar 

  11. Chen, C.-F., Lu, L.-G., Hu, Z.-Q., Peng, X.-X., Huang, Z.-T.: Tetrahedron 61, 3853–3858 (2005)

    Article  CAS  Google Scholar 

  12. Organo, V.G., Sgarlata, V., Firouzbakht, F., Rudkevich, D.M.: Chem. Eur. J. 13, 4014–4023 (2007)

    Article  CAS  Google Scholar 

  13. Xu, H., Kinsel, G.R., Zhang, J., Li, M., Rudkevich, D.M.: Tetrahedron 59, 5837–5848 (2003)

    Article  CAS  Google Scholar 

  14. Xu, H., Rudkevich, D.M.: Chem. -Eur. J. 10, 5432–5442 (2004)

    Article  CAS  Google Scholar 

  15. Xu, H., Rudkevich, D. M.: J. Org. Chem. 69, 8609–8617 (2004)

    Article  CAS  Google Scholar 

  16. Luo, J., Shen, L.-C., Chung W.-S.: J. Org. Chem. 75, 464–467 (2010)

    Article  CAS  Google Scholar 

  17. Li, S.-Z., Shi, J., Yang, K., Luo, J.: Tetrahedron. 68, 8557–8563 (2012)

    Article  CAS  Google Scholar 

  18. Li, S.-Z., Yang, K., Liu, H.-B., Xia, Y.-X., Zhu, R.-X., Luo, J., Wan, Q.: Tetrahedron Lett. 54, 5901–5906 (2013)

    Article  CAS  Google Scholar 

  19. Wan, Y., Mitkin, O., Barnhurst, L., Kurchan, A., Kutateladze, A.: Org. Lett. 2, 3817–3819 (2000)

    Article  CAS  Google Scholar 

  20. Yang Y., Swager T.M.: Macromolecules 39, 2013–2015 (2006)

    Article  CAS  Google Scholar 

  21. Yang Y., Swager T.M.: Macromolecules 40, 7437–7440 (2007)

    Article  CAS  Google Scholar 

  22. Lu Y., Xiao C., Yu Z., Zeng X., Ren Y., Li C.: J. Mater. Chem. 19, 8796–8802, (2009)

    Article  CAS  Google Scholar 

  23. Ogoshi T., Nishida Y., Yamagishi T.-A., Nakamoto Y.: Polym. Chem. 1, 203–206 (2010)

    Article  CAS  Google Scholar 

  24. Rambo B.M., Kim S.K., Kim J.S., Bielawski C.W., Sessler J.L.: Chem. Sci. 1, 716–722 (2010)

    Article  CAS  Google Scholar 

  25. Wiktorowicz S., Aseyev V., Tenhu H.: Polym. Chem. 3, 1126–1129 (2012)

    Article  CAS  Google Scholar 

  26. Wiktorowicz S., Tenhu H., Aseyev V.: Macromolecules 46, 6209–6216 (2013)

    Article  CAS  Google Scholar 

  27. Szumna, A.: Chem. Soc. Rev. 39, 4274–4285 (2010)

    Article  CAS  Google Scholar 

  28. Zhang, W.-Z., Ma, H., Xiang, G.-Y., Luo, J., Chung W.-S.: ChemistrySelect 1, 2486–2491 (2016)

    Article  CAS  Google Scholar 

  29. Gudeangadi, P.G., Sakamoto, T., Shichibu, Y., Konishi, K., Nakano, T.: ACS Macro Lett. 4, 901–906 (2015)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The authors are grateful to the National Natural Science Foundation of China (NSFC) (Grant No. 20902029) and the Fundamental Research Funds for the Central Universities (HUST: No. 2014QN130) for financial support. The Analytical and Testing Center of Huazhong University of Science and Technology is thanked for measurement service.

Author information

Authors and Affiliations

Authors

Corresponding authors

Correspondence to Jun Luo or Jun-Min Liu.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (PDF 2722 KB)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Ma, H., Zhang, WZ., Luo, J. et al. Synthesis of a linearly linked triscalixarene consisting of calix[4]arene units with combined axial chirality and inherent chirality. J Incl Phenom Macrocycl Chem 89, 91–104 (2017). https://doi.org/10.1007/s10847-017-0722-8

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10847-017-0722-8

Keywords

Navigation