Skip to main content
SpringerLink
Log in

Synthesis of chiral bisacylphosphine oxides and their application as initiators in helix-sense-selective photopolymerization

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

Abstract

Three new chiral bisacylphosphine oxides, (−)-bis(menthylformyl)phenylphosphine oxide (1a), (+)-bis(2,4,6-trimethylbenzoyl)menthylphosphine oxide (2a), and (−)-bis(menthylformyl)menthylphosphine oxide (3a), were synthesized using menthol as a chiral source. The synthesized new chiral bisacylphosphine oxides were used as photoinitiators for the polymerization of 1-phenyldibenzosuberyl methacrylate (PDBSMA). The polymerization initiated by chiral bisacylphosphine oxides under UV light irradiation is helix-sense-selective. Among the three prepared chiral bisacylphosphine oxides, the helix-sense-selectivity of bis(menthylformyl)menthylphosphine oxide is highest. The highest specific rotation of poly(1-phenyldibenzosuberyl methacrylate) at 365 nm is +416. The feed molar ratio of monomer to chiral bisacylphosphine oxide and the polymerization temperature have an influence on the helix-sense-selectivity. The lower the feed molar ratio of monomer to chiral bisacylphosphine oxide, the better the helix-sense-selectivity is. The increase of polymerization temperature is propitious to increase the helix-senseselectivity of the photopolymerization.

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

We’re sorry, something doesn't seem to be working properly.

Please try refreshing the page. If that doesn't work, please contact support so we can address the problem.

References

  1. Y. Yagci, S. Jockusch, and N. J. Turro, Macromolecules, 43, 6245 (2010).

    Article  CAS  Google Scholar 

  2. J. P. Fisher, D. Dean, P. S. Engel, and A. G. Mikos, Annu. Rev. Mater. Res., 31, 171 (2001).

    Article  CAS  Google Scholar 

  3. T. Sumiyoshi and W. Schnabel, Makromol. Chem., 186, 1811 (1985).

    Article  CAS  Google Scholar 

  4. U. Kolczak, G. Rist, K. Dietliker, and J. Wirz, J. Am. Chem. Soc., 118, 6477 (1996).

    Article  CAS  Google Scholar 

  5. T. Sumiyoshi, W. Schnabel, and A. Henne, J. Photochem., 32, 191 (1986).

    Article  CAS  Google Scholar 

  6. T. Sumiyoshi, W. Schnabel, and A. Henne, J. Photochem., 32, 119 (1986).

    Article  CAS  Google Scholar 

  7. H. F. Sobhi, J. M. Masnovi, and A. T. Riga, J. Therm. Anal. Calorim., 101, 1065 (2010).

    Article  CAS  Google Scholar 

  8. C. Decker, K. Zahouily, D. Decker, T. Nguyen, and Thi Viet, Polymer, 42, 7551 (2001).

    Article  CAS  Google Scholar 

  9. I. Gatlik, P. Rzadek, G. Gescheidt, G. Rist, B. Hellrung, J. Wirz, K. Dietliker, G. Hug, M. Kunz, and J. P. Wolf, J. Am. Chem. Soc., 121, 8332 (1999).

    Article  CAS  Google Scholar 

  10. G. W. Sluggett, P. F. McGarry, I. V. Koptyug, and N. J. Turro, J. Am. Chem. Soc., 118, 7367 (1996).

    Article  CAS  Google Scholar 

  11. E. Yashima, K. Maeda, H. Lida, Y. Furusho, and K. Nagai, Chem. Rev., 109, 6102 (2009).

    Article  CAS  Google Scholar 

  12. T. Nakano and Y. Okamato, Chem. Rev., 101, 4013 (2001).

    Article  CAS  Google Scholar 

  13. T. Nakano and Y. Okamoto, Macromol. Rapid Commun., 21, 603 (2000).

    Article  CAS  Google Scholar 

  14. T. Nakano, Y. Shikisai, and Y. Okamoto, Polym. J., 28, 51 (1996).

    Article  CAS  Google Scholar 

  15. N. Hoshikawa, Y. Hotta, and Y. Okamoto, J. Am. Chem. Soc., 125, 12380 (2003).

    Article  Google Scholar 

  16. N. Hoshikawa, C. Yamamoto, Y. Hotta, and Y. Okamoto, Polym. J., 38, 1258 (2006).

    Article  CAS  Google Scholar 

  17. Y. Okamoto, T. Nakano, Y. Shikisai, and M. Mori, Macromol. Symp., 89, 479 (1995).

    Article  CAS  Google Scholar 

  18. J. G. Smith and G. F. Wright, J. Org. Chem., 17, 1116 (1952).

    Article  CAS  Google Scholar 

  19. D. Cunningham, E. T. Gallagher, D. H. Grayson, P. J. McArdle, C. B. Storey, and D. J. Wilcock, J. Chem. Soc. Perkin Trans. 1, 23, 2692 (2002).

    Article  Google Scholar 

  20. S. Wu, N. F. Yang, L. W. Yang, J. Cao, and J. Liu, J. Polym. Sci. Part A: Polym. Chem., 48, 1441 (2010).

    Article  CAS  Google Scholar 

  21. M. Hidai, H. Mizuta, H. Yagi, Y. Nagai, K. Hata, and Y. Uchida, J. Organomet. Chem., 232, 89 (1982).

    Article  CAS  Google Scholar 

  22. D. Leppard, E. Eichenberger, R. Kaeser, G. Hug, and U. Schwendimann, Ciba Speciality Chemicals Holding Inc., WO Patent 00/32612 (2000).

  23. S. Jockusch and N. J. Turro, J. Am. Chem. Soc., 120, 11773 (1998).

    Article  CAS  Google Scholar 

  24. D. Leppard and M. Köhler, Ciba-Geigy AG. Basel, DE Patent 195 32 358 (1994).

  25. W. Rutsch, K. Dietliker, and R. G. Hall, Ciba Geigy AG, US Patent 5218009 (1993).

  26. T. Nakano, A. Matsuda, and Y. Okamoto, Polym. J., 28, 556 (1996).

    Article  CAS  Google Scholar 

  27. T. Nakano, M. Mori, and Y. Okamoto, Macromolecules, 26, 867 (1993).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Key Laboratory of Environmentally Friendly Chemistry and Applications of Ministry of Education, College of Chemistry, Xiangtan University, 411105, Hunan, P. R. China

    Jia-An Zhang, Nian-Fa Yang, Li-Wen Yang, Ye-Hui Chen & Jin Zhang

  2. School of Pharmacy, Hubei University of Science and Technology, 437100, Hubei, P. R. China

    Jia-An Zhang & Shi Wu

Authors
  1. Jia-An Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Nian-Fa Yang
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Li-Wen Yang
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Shi Wu
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Ye-Hui Chen
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Jin Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Nian-Fa Yang.

Electronic supplementary material

Rights and permissions

Reprints and permissions

About this article

Cite this article

Zhang, JA., Yang, NF., Yang, LW. et al. Synthesis of chiral bisacylphosphine oxides and their application as initiators in helix-sense-selective photopolymerization. Macromol. Res. 21, 641–648 (2013). https://doi.org/10.1007/s13233-013-1077-7

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13233-013-1077-7

Keywords

Search

Navigation