DOI QR코드

DOI QR Code

Oxidative Coupling Polymerization of Diethynylsilane Derivatives and 1,2-Diethynyl-1,1,2,2-tetramethyldisilane

  • Published : 2006.06.20

Abstract

We have carried out the Glaser oxidative coupling polymerizations of diethynyldiphenylsilane, diethynylmethylphenylsilane,diethynylmethyloctylsilane, and 1,2-diethynyl-1,1,2,2-tetramethyldisilane to afford polycarbosilanes containing diethynyl and organosilane groups in the main chain, such as poly(diethynyldiphenylsilane), poly(diethynylmethylphenylsilane), poly(diethynylmethyloctylsilane), and poly(1,2-diethynyl-1,1,2,2-tetramethyldisilane), respectively. These obtained materials are almost insoluble in common organic solvents such as $CHCl_3$ and THF probably due to the presence of a rigid rod diacetylene group along the polymer main chain. Therefore, the polymers were characterized using several spectroscopic methods in solid state. FTIR spectra of all the polymeric materials show that the characteristic $C \equiv C$ stretching frequencies appear at 2147-2154 $cm ^{-1}$, in particular. The polymers in the solid state exhibit that the strong maximum excitation peaks appear at 260-283 nm and the strong maximum fluorescence emission bands at 367-412 nm, especially. Thermogravimetric analysis of the materials shows that about 55-68% of the initial polymer weights remain at 400 ${^{\circ}C}$ in nitrogen.

Keywords

References

  1. Ohshita, J.; Kunai, A. Acta Polym. 1998, 49, 379 https://doi.org/10.1002/(SICI)1521-4044(199808)49:8<379::AID-APOL379>3.0.CO;2-Z
  2. Corriu, R. J. P.; Guerin, C.; Henner, B. J. L.; Kuhlmann, Th. Chem. Mater. 1990, 2, 351 https://doi.org/10.1021/cm00010a008
  3. Brefort, J. L.; Corriu, R. J. P.; Gerbier, Ph.; Guérin, C.; Henner, B. J. L.; Jean, A.; Kuhlmann, Th. Garnier, F.; Yassar, A. Organometallics 1992, 11, 2500 https://doi.org/10.1021/om00043a037
  4. Ishikawa, M.; Hasegawa, Y.; Kunai, A.; Yamanaka, T. R. J. Organomet. Chem. 1990, 381, C57 https://doi.org/10.1016/0022-328X(90)80071-7
  5. Ijadi-Maghsoodi, S.; Barton, T. J. Macromolecules 1990, 23, 4485 https://doi.org/10.1021/ma00222a027
  6. Corriu, R. J. P.; Gerbier, Ph.; Guerin, C.; Henner, B.; Fourcade, R. J. Organomet. Chem. 1993, 449, 111 https://doi.org/10.1016/0022-328X(93)80113-P
  7. Keller, T. D.; Homrighausen, C. L. J. Polym. Sci., Part A: Polym. Chem. 2002, 40, 88 https://doi.org/10.1002/pola.10091
  8. Tanaka, K.; Nakajima, K.; Okada, M.; Yamabe, T.; Ishikawa, M. Organometallics 1991, 10, 2679 https://doi.org/10.1021/om00054a032
  9. Maxka, J.; Teramae, H. Macromolecules 1999, 32, 7045 https://doi.org/10.1021/ma990001f
  10. Xu, C.; Wakamiya, A.; Yamaguchi, S. J. Am. Chem. Soc. 2005, 127, 1638 https://doi.org/10.1021/ja042964m
  11. Son, H.-J.; Han, W.-S.; Kim, H.; Kim, C.; Ko, J.; Lee, C.; Kang, S. O. Organometallics 2006, 25, 766 https://doi.org/10.1021/om050991v
  12. Lee, J. H.; Park, Y. T. Bull. Korean Chem. Soc. 2004, 25, 889 https://doi.org/10.5012/bkcs.2004.25.6.889
  13. Kim, M. H.; Park, Y. T. Bull. Korean Chem. Soc. 2005, 26, 488 https://doi.org/10.5012/bkcs.2005.26.3.488
  14. Kim, E. J.; Park, J. W.; Kim, Y.-R.; Park, Y. T. Bull. Korean Chem. Soc. 2003, 24, 484 https://doi.org/10.5012/bkcs.2003.24.4.484
  15. Hwang, I.-W.; Song, N. W.; Kim, D.; Park, Y. T.; Kim, Y.-R. J. Polym. Sci., Part B: Polym. Phys. 1999, 37, 2901 https://doi.org/10.1002/(SICI)1099-0488(19991015)37:20<2901::AID-POLB10>3.0.CO;2-4
  16. Choi, S. H.; Hwang, I.-W.; Kim, S. H.; Park, Y. T.; Kim, Y.-R. J. Polym. Sci., Part B: Polym. Phys. 2002, 40, 1298 https://doi.org/10.1002/polb.10190
  17. Brook, M. A. In Silicon in Organic, Organometallic, and Polymer Chemistry; John Wiley & Sons, Inc.: New York, 2000
  18. Bellamy, L. J. In The Infra-red of Complex Molecules, 3rd ed.; John Wiley and Sons: New York, 1975
  19. Pretsch, E.; Buhlmann, P.; Affolter, C. In Structure Determination of Organic Compounds, Tables of Spectral Data, 3rd ed.; Springer-Verlag: Berlin, 2000
  20. Parnell, D. R.; Macaione, D. P. J. Polym. Sci., Part A: Polym. Chem. 1973, 11, 1107 https://doi.org/10.1002/pol.1973.170110516
  21. March, J. In Advanced Organic Chemistry; Reactions, Mechanism, and Structure, 3rd ed.; John Wiley and Sons: New York, 1985
  22. Hartbaum, C.; Mauz, E.; Roth, G.; Weissenbach, K.; Fischer, H. Organometallics 1999, 18, 2619 https://doi.org/10.1021/om990145i
  23. Dawson, D. J.; Fleming, W. W.; Lyerla, J. R.; Economy, J. In ACS Symposium Series No. 282 Reactive Oligomers; Harris, F. W., Spinelli, H. J., Eds.; American Chemical Society: Washington, DC, 1985
  24. Barashkov, N. N.; Gunder, O. A. In Fluorescent Polymers; Ellis Horwood: New York, 1994
  25. Armarego, W. L. F.; Perrin, D. D. In Purification of Laboratory Chemicals, 4th ed.; Butterworth-Heinemann: Oxford, 1996
  26. Luneva, L. K.; Sladkov, A. M.; Korshak, V. V. Izv. Akad. Nauk SSSR, Otd. Khim. Nauk 1968, 160
  27. Korshak, V. V.; Sladkov, A. M.; Luneva, L. K. Izv. Akad. Nauk SSSR, Otd. Khim. Nauk 1962, 2251

Cited by

  1. Synthesis and Properties of Polymers with an Organosilicon–Acetylene Backbone vol.28, pp.5, 2018, https://doi.org/10.1007/s10904-018-0854-3
  2. A Synthetic Approach to Oligomeric Phenylethynylsilylenes vol.20, pp.4, 2010, https://doi.org/10.1007/s10904-010-9378-1
  3. Synthesis and Properties of Poly(carbomethyloctylsiloxane)s by Melt Copolymerization of Bis(diethylamino)methyloctylsilane and Aryldiol Derivatives vol.29, pp.12, 2006, https://doi.org/10.5012/bkcs.2008.29.12.2373
  4. Synthesis and Characterization of Poly(arylene-ethynylene)s with Ferrocene Unit by Reaction of 1,1'-Bis(ethynyldimethylsilyl)ferrocene and Aromatic Dihalides vol.30, pp.2, 2009, https://doi.org/10.5012/bkcs.2009.30.2.309
  5. Melt Copolymerization Reactions between 1,3-Bis(diethylamino)tetramethyldisiloxane and Aryldiol Derivatives vol.32, pp.4, 2011, https://doi.org/10.5012/bkcs.2011.32.4.1303
  6. Synthesis and Photoelectronic Properties of Thermally Stable Poly[oxy(2,7-fluoren-9-onenylene)oxy(diorganosilylene)]s vol.33, pp.6, 2012, https://doi.org/10.5012/bkcs.2012.33.6.2031