Skip to main content
SpringerLink
Log in

Synthesis and characterization of two [2]catenanes based on phenylene-diacetylene crown ethers

  • Published:
Chemical Research in Chinese Universities Aims and scope

Abstract

Two charged donor-acceptor [2]catenanes were synthesized by the cyclization of the π-acceptor 1,1′-[1, 4-phenylenebis-(methylene)]bis(4,4′-bipyridinium)bis(hexafluorophosphate)(2) and bis(bromomethyl)benzene with the templates of the π-donor phenylene-diacetylene crown ethers 1a and 1b in the yields of 31%, 35%, respectively. The mass spectra, 1H and 13C NMR spectra confirm that the phenylene-diacetylene crown ethers, with a nonaromatic π-system, successfully template the cyclization of CBPQT4+. The X-ray crystallography analysis shows that the CBPQT4+ ring encircles around the phenylene motif of the crown ethers, leaving the 1,3-butadiyne fragment out of the cavity of CBPQT4+ ring. The mechanically interlocked structure of [2]catenanes was stabilized by the cooperative effects of π-stacking and hydrogen bonding interactions.

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

Similar content being viewed by others

References

  1. Balzani V., Credi A., Raymo F. M., Stoddart J. F., Angew. Chem. Int. Ed., 2000, 39, 3348

    Article  CAS  Google Scholar 

  2. Bruns C. J., Stoddart J. F., Nat. Nanotech., 2013, 8, 9

    Article  CAS  Google Scholar 

  3. Fahrenbach A. C., Warren S. C., Incorvati J. T., Avestro A. J., Barnes J. C., Stoddart J. F., Grzybowski B. A., Adv. Mater., 2013, 3, 331

    Article  Google Scholar 

  4. Natali M., Giordani S., Chem. Soc. Rev., 2012, 41, 4010

    Article  CAS  Google Scholar 

  5. Carlone A., Hänni K. D., Leigh D. A., Lewandowski B., Angew. Chem. Int. Ed., 2012, 51, 5166

    Article  Google Scholar 

  6. Sun Y. L., Yang Y. W., Wu W., Zhang X. A., Chem. J. Chinese Universities, 2012, 33(8), 1635

    CAS  Google Scholar 

  7. Yang B., Ma Y. G., Shen J. C., Chem. J. Chinese Universities, 2008, 29(12), 2643

    CAS  Google Scholar 

  8. Vögtle F., Meier S., Hoss R., Angew. Chem. Int. Ed., 1992, 31, 1619

    Article  Google Scholar 

  9. Chambron J. C., Ccollin J. P., Heitz V., Sauvage J. P., Eur. J. Org. Chem., 2004, 1627

    Google Scholar 

  10. Miljanic O. S., Dichtel W. R., Mortezaei S., Stoddart J. F., Org. Lett., 2005, 8, 4835

    Article  Google Scholar 

  11. Miljanic O. S., Dichtel W. R., Khan S. I., Stoddart J. F., J. Am. Chem. Soc., 2007, 129, 8236

    Article  CAS  Google Scholar 

  12. Leigh D. A., Lusby P. J., McBurney R. T., Morelli A., Slawin A. M. Z., Thomson A. R., Walker D. B., J. Am. Chem. Soc., 2009, 131, 3762

    Article  CAS  Google Scholar 

  13. Cougnon F. B., Jenkins N. A., Pantoş G. D., Sanders J. K., Angew. Chem. Int. Ed., 2012, 51, 1443

    Article  CAS  Google Scholar 

  14. Chung M. K., Lee S. J., Waters M. L., Gagné M. R., J. Am. Chem. Soc., 2012, 134, 11430

    Article  CAS  Google Scholar 

  15. Yan X. Z., Wei P. F., Li Z. T., Zheng B., Dong S. Y., Huang F. H., Zhou Q. Z., Chem. Commun., 2013, 49, 2512

    Article  CAS  Google Scholar 

  16. Ballardini R., Balzani V., Credi A., Gandolfi M. T., Venturi M., Acc. Chem. Res., 2001, 34, 445

    Article  CAS  Google Scholar 

  17. Barin G., Coskun A., Fouda M. M. G., Stoddart J. F., ChemPlusChem., 2012, 77, 159

    Article  CAS  Google Scholar 

  18. Fujita M., Acc. Chem. Res., 1999, 32, 53

    Article  CAS  Google Scholar 

  19. Anelli P. L., Ashton P. R., Ballardini R., J. Am. Chem. Soc., 1992, 114, 193

    Article  CAS  Google Scholar 

  20. Liu Y., Bruneau A., He J., Abliz Z., Org. Lett., 2008, 10, 765

    Article  CAS  Google Scholar 

  21. Miljanic O. S., Dichtel W. R., Mortezaei S., Stoddart J. F., Org. Lett., 2006, 8, 4835

    Article  CAS  Google Scholar 

  22. Feng Y. H., Li J. N., Jiang L. S., Gao Z. H., Huang W. C., Jiang F., Luo N. H., Han S. J., Zeng R. H., Yang D. Q., Eur. J. Org. Chem., 2011, 562

    Google Scholar 

  23. Pedersen C. J., J. Am. Chem. Soc., 1967, 89, 7017

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. School of Chemistry and Environment, South China Normal University, Guangzhou, 510006, P. R. China

    Mu-juan Chen, Song-gen Zhou, Mei Li, Chun-yan Lei, Rui Xiao & La-sheng Jiang

Authors
  1. Mu-juan Chen
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Song-gen Zhou
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Mei Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Chun-yan Lei
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Rui Xiao
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. La-sheng Jiang
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to La-sheng Jiang.

Additional information

Supported by the National Natural Science Foundation of China(No.21072066) and the Natural Science Foundation of Guangdong Province of China(No.8151063101000015).

Rights and permissions

Reprints and permissions

About this article

Cite this article

Chen, Mj., Zhou, Sg., Li, M. et al. Synthesis and characterization of two [2]catenanes based on phenylene-diacetylene crown ethers. Chem. Res. Chin. Univ. 29, 1094–1097 (2013). https://doi.org/10.1007/s40242-013-3218-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s40242-013-3218-0

Keywords

Search

Navigation