Skip to main content
Log in

Synthesis of Chromophore Core Fréchet-Type Dendrimer by Oxidative Homo-Coupling of Terminal Alkyne

  • Article
  • Published:
Macromolecular Research Aims and scope Submit manuscript

Abstract

The alkyne-functionalized Fréchet-type dendrons 2-Dm containing benzamine were synthesized by N-alkylation of the corresponding dendritic benzyl chlorides with 4-ethynylaniline. The oxidative homo-coupling reaction of the alkyne-functionalized Fréchet-type dendrons 2-Dm was allowed to provide the first through fourth generation dendrimers 3-Gm with 1,4-diphenylbuta-1,3-diynes at chromophore core in high yields. Their structure of dendrimers was confirmed by 1H and 13C NMR spectroscopy, IR spectroscopy, mass spectrometry, and GPC analysis. The photophysical properties of the synthesized dendrimers was investigated.

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.

Similar content being viewed by others

References

  1. S.-C. Lo and P. L. Burn, Chem. Rev., 107, 1097 (2007).

    Article  CAS  Google Scholar 

  2. Jiang, D.-L. Jiang and T. Aida, Nature, 388, 454 (1997).

    Article  CAS  Google Scholar 

  3. D.-L. Jiang and T. Aida, J. Am. Chem. Soc., 120, 10895 (1998).

    Article  CAS  Google Scholar 

  4. T. Sato, D.-L. Jiang, and T. Aida, J. Am. Chem. Soc., 121, 10658 (1999).

    Article  CAS  Google Scholar 

  5. A. W. Freeman, S. C. Koene, P. R. L. Malenfant, M. E. Thompson, and J. M. J. Fréchet, J. Am. Chem. Soc., 122, 12385 (2000).

    Article  CAS  Google Scholar 

  6. A. Nantalaksakul, D. R. Reddy, C. J. Bardeen, and S. Thayumanavan, Photosynth. Res., 87, 133 (2006).

    Article  CAS  Google Scholar 

  7. K. Minoru, M. Shinjiro, T. Satoshi, H. Kazuyuki, Y. Hiroyuki, and M. Hiroshi, Chem. Lett., 31, 394 (2002).

    Article  Google Scholar 

  8. D. Astruc, E. Boisselier, and C. Ornelas, Chem. Rev., 110, 1857 (2010).

    Article  CAS  Google Scholar 

  9. V. Paolucci, S. L. Mejlsøe, M. Ficker, T. Vosch, and J. B. Christensen, J. Phys. Chem. B, 120, 9576 (2016).

    Article  CAS  Google Scholar 

  10. A.-M. Caminade, A. Hameau, and J.-P. Majoral, Chem. Eur. J., 15, 9270 (2009).

    Article  CAS  Google Scholar 

  11. E. N. Augustus, E. T. Allen, A. Nimibofa, W. Donbebe, Am. J. Polym. Sci., 7, 8 (2017).

    CAS  Google Scholar 

  12. A. Adronov and J. M. J. Fréchet, Chem. Commun., 1701 (2000).

  13. S. H. Hwang, C. N. Moorefield, and G. R. Newkome, Chem. Soc. Rev., 37, 2543 (2008).

    Article  CAS  Google Scholar 

  14. S. C. Lo and P. L. Burn, Chem. Rev., 107, 1097 (2007).

    Article  CAS  Google Scholar 

  15. P. L. Burn, S. C. Lo, and I. D. W. Samuel, Adv. Mater., 19, 1675 (2007).

    Article  CAS  Google Scholar 

  16. G. R. Newkome, C. N. Moorefield, and F. Vögtle, Dendrimers and Dendrons: Concepts, Synthesis, Applications, Wiley-VCH, Weinheim, 2001.

    Book  Google Scholar 

  17. J. M. J. Fréchet and D. A. Tomalia, Dendrimers and Other Dendritic Polymers, John Wiely & Sons Ltd., Chichester, 2002.

    Google Scholar 

  18. F. Diederich, P. J. Stang, Eds. In Metal-Catalyzed Crosscoupling Reactions, Wiley-VCH, Weinheim, 1998.

    Google Scholar 

  19. J. M. Tour, Chem. Rev., 96, 537 (1996).

    Article  CAS  Google Scholar 

  20. R. E. Martin and F. Diederich, Angew. Chem. Int. Ed., 38, 1350 (1999).

    Article  Google Scholar 

  21. M. Yamaguchi, H.-J. Park, M. Hirame, K. Torisu, S. Nakamura, T. Minami, H. Nishihara, and T. Hiraoka, Bull. Chem. Soc. Jpn., 67, 1717 (1994).

    Article  CAS  Google Scholar 

  22. J.-M. Lehn, Supramolecular Chemistry: Concepts and Perspectives, VCH, Weinheim, 1995.

    Book  Google Scholar 

  23. J. W. Lee, S. C. Han, U. Y. Lee, B.-K. Kim, and J. H. Kim, Bull. Korean Chem. Soc., 30, 1925 (2009).

    Article  CAS  Google Scholar 

  24. S. C. Han, S. C. Kim, and J. W. Lee, Bull. Korean Chem. Soc., 32, 3899 (2011).

    Article  CAS  Google Scholar 

  25. J. W. Lee, S. C. Han, H. J. Kim, J. H. Kim, U. Y. Lee, B.-K. Kim, S. R. Sung, H.-S. Kang, J. H. Kim, and D.-S. Hur, Polym. Korea, 31, 417 (2007).

    CAS  Google Scholar 

Download references

Acknowledgment

This research was supported by the Dong-A University Research Fund.

Author information

Authors and Affiliations

Authors

Corresponding authors

Correspondence to Sung-Ho Jin or Jae Wook Lee.

Additional information

Publisher’s Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Han, S.C., Song, T.G., Jin, SH. et al. Synthesis of Chromophore Core Fréchet-Type Dendrimer by Oxidative Homo-Coupling of Terminal Alkyne. Macromol. Res. 29, 430–434 (2021). https://doi.org/10.1007/s13233-021-9051-2

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13233-021-9051-2

Keywords

Navigation