Journal of Integrative Natural Science (통합자연과학논문집)

The Basic Science Institute Chosun University (조선대학교 기초과학연구원)
권호 표지
DOI QR코드

DOI QR Code

Radical Polymerization of Vinyl Monomers to Poly(vinyl)s having nBu3Sn end Groups with Biological Activity

  • Park, Jaeyoung (Department of Biotechnology, Chosun University) ;
  • Lee, Beomgi (Department of Biotechnology, Chosun University) ;
  • Kim, Seongsim (Department of Biotechnology, Chosun University) ;
  • Cheong, Hyeonsook (Department of Biotechnology, Chosun University) ;
  • Gwak, Gyeongja (Department of Complementally and Alternative Medicine, Chosun University) ;
  • Lee, Ki Bok (Department of Chemistry and Nanotechnology Research Center, Chonnam National University) ;
  • Woo, Hee-Gweon (Department of Chemistry and Nanotechnology Research Center, Chonnam National University)
  • Received : 2013.03.05
  • Accepted : 2013.06.24
  • Published : 2013.06.30
Download PDF
⟨ Previous Next ⟩

Abstract

$Bu_3Sn$-endded poly(vinyl)s with biological activity were obtained by the radical polymerization of vinyl monomers using thianthrene cation radical/$^nBu_3H$. Thianthrene cation and stannyl radicals promoted the homopolymerization and copolymerization of styrene and ethyl vinyl ether having number average molecular weights of 2000-3100. Tributyltin hydride functions as a chain transfer agent. Such polymereization by cationic thianthrene and stannyl radicals could provide some clues for the biological reaction in living animals. Plausible polymerization mechanisms were suggested.

Keywords

References

  1. A. J. Bard, A. Ledwith, and H. J. Shine, "Formation, properties and reactions of cation radicals in solution", Adv. Phys. Org. Chem., Vol. 13, pp. 155-278, 1976 https://doi.org/10.1016/S0065-3160(08)60214-2
  2. L. Eberson, "Structure and mechanism in organic electrochemistry", Adv. Phys. Org. Chem., Vol. 12, pp. 1-129, 1976. https://doi.org/10.1016/S0065-3160(08)60330-5
  3. L. Magdzinski and Y. L. Chow, "Reactivities of amino and aminium radicals: oxidative photoaddition of tetramethyl-2-tetrazene to olefins", J. Am. Chem. Soc., Vol. 100, pp. 2444-2448, 1978. https://doi.org/10.1021/ja00476a030
  4. H. J. Shine, B. K. Bandlish, S. R. Mani, and A. G. Padilla, "Ion radicals. 43. Addition of thianthrene and phenoxathiin cation radicals to alkenes and alkynes", J. Org. Chem., Vol. 44, pp. 915-917, 1979. https://doi.org/10.1021/jo01320a004
  5. D. J. Siegwart, A. Srinivasan, S. A. Bencherif, A. Karunanidhi, J. K. Oh, S. Vaidya, R. Jin, J. O. Hollinger, and K. Matyjaszewski, "Cellular uptake of functional nanogels prepared by inverse miniemulsion ATRP with encapsulated proteins, carbohydrates, and gold nanoparticles", Biomacromolecules, Vol. 10, pp. 2300-2309, 2009. https://doi.org/10.1021/bm9004904
  6. H. Gao and K. Matyjaszewski, "Synthesis of functional polymers with controlled architecture by CRP of monomers in the presence of cross-linkers: From stars to gels", Prog. Polym. Sci., Vol. 34, pp. 317-350, 2009. https://doi.org/10.1016/j.progpolymsci.2009.01.001
  7. N. Bortolamei, A. A. Isse, V. B. Di Marco, A. Gennaro, and K. Matyjaszewski, "Thermodynamic properties of copper complexes used as catalysts in atom transfer radical polymerization", Macromolecules, Vol. 43, pp. 9257-9267, 2010. https://doi.org/10.1021/ma101979p
  8. Odian, G. "Principles of polymerization", 3rd ed., Wiley, New York, Chapter 5, 1991.
  9. H. R. Allcock and F. W. Lampe, "Contemporary polymer chemistry", 2nd ed., Prentice-Hall, Singapore, Chapter 3, 1992.
  10. G. Mengoli and G. Vidotto, "Electrochemically generated 9.10-diphenylanthracene radical cations as initiators of polymerization processes", Makromol. Chem., Vol. 150, pp. 277-282, 1971. https://doi.org/10.1002/macp.1971.021500125
  11. B. L. Funt, W. Severs, and A. Glasel, "Rotating ring-disk electrode studies of the reaction of stable radical cations with styrene and isobutyl vinyl ether", J. Polym. Sci. Polym. Chem. Ed., Vol. 14, pp. 2763- 2771, 1976. https://doi.org/10.1002/pol.1976.170141115
  12. A. Glasel, K. Murray, and B. L. Funt, "Comparative reactivities of electrogenerated radical cations in cationic polymerization", Makromol. Chem., Vol. 177, pp. 3345-3358, 1976. https://doi.org/10.1002/macp.1976.021771119
  13. E. Oberrauch, T. Salvatori, and S. Cesca, "Perylene cation radical as initiator of cationic polymerization", J. Polym. Sci. Polym. Lett. Ed., Vol. 16, pp. 345-350, 1978. https://doi.org/10.1002/pol.1978.130160706
  14. H. J. Shine and J. J. Silber, "Ion radicals. XXIV. Reaction of thianthrene perchlorate with ammonia", J. Am. Chem. Soc., Vol. 94, pp. 1026-1027, 1972. https://doi.org/10.1021/ja00758a069
  15. B. K. Bandlish, A. G. Padilla, and H. J. Shine, "Ion radicals. XXXIII. Reactions of 10-methyl- and 10-phenylphenothiazine cation radicals with ammonia and amines. Preparation and reactions of 5-(N-alkyl)sulfilimines and 5-(N,N-dialkylamino) sulfonium salts", J. Org. Chem., Vol. 40, pp. 2590- 2595, 1975. https://doi.org/10.1021/jo00906a004
  16. K. Kim, V. J. Hull, and H. J. Shine, "Ion radicals. XXIX. Reaction of thianthrene cation radical perchlorate with some benzene derivatives", J. Org. Chem., Vol. 39, pp. 2534-2537, 1974. https://doi.org/10.1021/jo00931a016
  17. S. Lochynski, H. J. Shine, M. Soroka, and T. K. Venkatachalam, "Evidence for electron transfer in reactions of thianthrene cation radical with dialkylmercurials", J. Org. Chem., Vol. 55, pp. 2702-2713, 1990. https://doi.org/10.1021/jo00296a029
  18. K. Kim and H. J. Shine, "Ion radicals. XXXI. Reaction of thianthrene cation radical perchlorate with ketones. Formation of $\beta$- ketoalkylsulfonium perchlorates and ylides", Tetrahedron Lett., Vol. 15, pp. 4413-4416, 1974. https://doi.org/10.1016/S0040-4039(01)92177-X
  19. H. J. Shine, B. K. Bandlish, S. R. Mani, and A. G. Padilla, "Ion radicals. 43. Addition of thianthrene and phenoxathiin cation radicals to alkenes and alkynes", J. Org. Chem., Vol. 44, pp. 915-917, 1979. https://doi.org/10.1021/jo01320a004
  20. A. K. M. M. Hoque, W. K. Lee, H. J. Shine, and D.-C. Zhao, "Reactions of thianthrene cation radical with oximes of cinnamaldehydes and unsaturated aromatic ketones in acetonitrile", J. Org. Chem., Vol. 56, pp. 1332-1334, 1991. https://doi.org/10.1021/jo00003a084
  21. R. P. Schreiner, S. E. Stevens, and M. Tien, "Oxidation of thianthrene by the ligninase of phanerochaete chrysosporium", Appl. Environ. Microbiol., Vol. 54, pp. 1858-1860, 1988.
  22. S. C. Mitchell and R. H. Waring, "Fate of thianthrene in rat", Xenobiotica, Vol. 28, pp. 93-101, 1998. https://doi.org/10.1080/004982598239786
  23. H. J. Shine and L. Pitte, "Ion-radicals. the reaction of thioaromatic compounds with acids. II. Diphenyl disulfide, thianthrene and thianthrene oxides", J. Am. Chem. Soc., Vol. 84, pp. 4798-4806, 1963.
  24. B. Li, S. Kim, J. Park, H. Cheong, J. E. Noh, and H.-G. Woo, "Polymerization of vinyl monomers initiated by thianthrene cation radical with potential biological activity", J. Chosun Natural Sci., Vol. 5, pp. 127-130, 2012. https://doi.org/10.13160/ricns.2012.5.2.127
  25. J. V. Crivello, J. L. Lee, and D. A. Conlon, "Developments in the design and applications of novel thermal and photochemical initiators for cationic polymerization", Macromol. Chem. Macromol. Symp., Vol. 13/14, pp. 145-160, 1988.
  26. A. Ledwith, "Advances in macromolecular chemistry", Ann. N. Y. Acad. Sci., Vol. 155, pp. 385-396. 1969.
  27. J. E. Huheey, E. A. Keiter, and R. L. Keiter, "Inorganic Chemistry", 4th ed., Harper Collins, New York, Appendix E, 1993.
  28. P. T. S. Wong, Y. K. Chau, O. Kramar, and G. A. Bengert, "Structure-toxicity relationship of tin compounds on algae", Canadian J. Fisheries and Aquatic Sci., Vol. 39, pp. 483-488, 1982. https://doi.org/10.1139/f82-066
  29. C.Boraiko, and J.Batt, "Evaluation of employee exposure to organic tin compounds used as stabilizers at PVC processing facilities", Tin Stabilizers Association Occup. Environ. Hyg., Vol. 2, pp. 73-76, 2005. https://doi.org/10.1080/15459620590906810
  30. T. Nakanishi, J.-I. Nishikawa, Y. Hiromori, H. Yokoyama, M. Koyanagi, S. Takasuga, J.-I. Ishizaki, M. Watanabe, S.-I. Isa, N. Utoguchi, N. Itoh, Y. Kohno, T. Nishihara, and K. Tanaka, "Trialkyltin compounds bind retinoid X receptor to alter human placental endocrine functions", Molecular Endocrinology, Vol. 19, pp. 2502-2516, 2005. https://doi.org/10.1210/me.2004-0397
  31. B. Li, S. Kim, J. Park, H. Cheong, J. E. Noh, and H.-G. Woo, manuscript in preparation.