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Melt Copolymerization Reactions between 1,3-Bis(diethylamino)tetramethyldisiloxane and Aryldiol Derivatives

  • Received : 2011.01.17
  • Accepted : 2011.03.02
  • Published : 2011.04.20

Abstract

Melt copolymerization reactions of bis(diethylamino)tetramethyldisiloxane with several aryldiols were carried out to afford poly(carbotetramethyldisiloxane)s containing fluorescent aromatic chromophore groups in the polymer main chain: poly{oxy(4,4'-biphenylene)oxytetramethyldisiloxane}, poly{oxy(1,4-phenylene)oxytetramethyldisiloxane}, poly[oxy{(4,4'-isopropylidene)diphenylene}oxytetramethyldisiloxane], poly[oxy{(4,4'-hexafluoroisopropylidene)diphenylene}oxytetramethyldisiloxane], poly{oxy(2,6-naphthalene)oxytetramethyldisiloxane}, poly[oxy{4,4'-(9-fluorenylidene)diphenylene}oxytetramethyldisiloxane], poly{oxy(fluorene-9,9-dimethylene)oxytetramethyldisiloxane}, and poly[oxy{4,4'-(9-fluorenylidene)bis(2-phenoxyethylene)}oxytetramethyldisiloxane]. These materials are soluble in common organic solvents such as $CHCl_3$ and THF. The FTIR spectra of all the polymers exhibit the characteristic Si-O-C stretching frequencies at 1021-1082 $cm^{-1}$. In the THF solution, the polymeric materials show strong maximum absorption peaks at 215-311 nm, with strong maximum excitation peaks at 250-310 nm, and strong maximum fluorescence emission bands at 310-360 nm. TGA thermograms indicate that most of the polymers are stable up to $200^{\circ}C$ with a weight loss of less than 10% in nitrogen.

Keywords

References

  1. Chen, J.; Cao, Y. Macromol. Rapid Commun. 2007, 28, 1714. https://doi.org/10.1002/marc.200700326
  2. Jenekhe, S. A. Chem. Mater. 2004, 16, 4381. https://doi.org/10.1021/cm041000r
  3. Clarson, S. J.; Semlyen, J. A. In Siloxane Polymers; PTR Prentice Hall, Inc.: Englewood Cliffs, New Jersey, 1993.
  4. Barashkov, N. N.; Gunder, O. A. In Fluorescent Polymers; Ellis Horwood: London, UK, 1994.
  5. Bisberg, J.; Cumming, W. J.; Gaudiana, R. A.; Hutchinson, K. D.; Ingwall, R. T.; Kolb, E. S.; Mehta, P. G.; Minns, R. A.; Petersen, C. P. Macromolecules 1995, 28, 386. https://doi.org/10.1021/ma00105a056
  6. Toulokhonova, I.; Bjerke-Kroll, B.; West, R. J. Organomet. Chem. 2003, 686, 101. https://doi.org/10.1016/S0022-328X(03)00672-7
  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. Dias, F. B.; Lima, J. C.; Macanita, A.; Clarson. S. J.; Horta, A.; Pierola, I. Macromolecules 2000, 33, 4772. https://doi.org/10.1021/ma992010u
  9. Xu, C.; Wakamiya, A.; Yamaguchi, S. J. Am. Chem. Soc. 2005, 127, 1638. https://doi.org/10.1021/ja042964m
  10. 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
  11. Backer, M. W.; Pernisz, U. C. Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 2001, 42(1), 122.
  12. Chandrasekhar, V. In Inorganic and Organometallic Polymers; Springer-Verlag: Berlin, 2005.
  13. Rubinsztajn, S.; Cella, J. A. Macromolecules 2005, 38, 1061. https://doi.org/10.1021/ma047984n
  14. Cai, G.; Weber, W. P. Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 2001, 42(1), 171.
  15. Nguyen, K.-A. T.; Shamshurin, A.; Clarke, S.; Matisons, J. Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 2004, 45(1), 706.
  16. Carraher, C. E., Jr.; Klimiuk, G. H. J. Polym. Sci., Part A-1: Polym. Chem. 1970, 8(4), 973. https://doi.org/10.1002/pol.1970.150080413
  17. Lee, J. H.; Park, Y. T. Bull. Korean Chem. Soc. 2004, 25, 889. https://doi.org/10.5012/bkcs.2004.25.6.889
  18. Kim, M. H.; Park, Y. T. Bull. Korean Chem. Soc. 2005, 26, 488. https://doi.org/10.5012/bkcs.2005.26.3.488
  19. 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
  20. Kim, J. H.; Park, Y. T. Bull. Korean Chem. Soc. 2006, 27, 869. https://doi.org/10.5012/bkcs.2006.27.6.869
  21. 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
  22. 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
  23. Yun, S. B.; Park, Y. T. Bull. Korean Chem. Soc. 2008, 29, 2373. https://doi.org/10.5012/bkcs.2008.29.12.2373
  24. Krieble, R. H.; Burkhard, C. A. J. Am. Chem. Soc. 1947, 69, 2689. https://doi.org/10.1021/ja01203a040
  25. Padmanaban, M.; Kakimoto, M.; Imai, Y. J. Polym. Sci. Part A: Polym. Chem. 1990, 28, 2997. https://doi.org/10.1002/pola.1990.080281109
  26. Pretsch, E.; Bühlmann, P.; Affolter, C. In Structure Determination of Organic Compounds, Tables of Spectral Data, 3rd ed.; Springer-Verlag: Berlin, 2000.
  27. Williams, E. A. NMR Spectroscopy of Organosilicon Compounds, In The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds., Wiley: Chichester, UK, 1989; Vol. 1, Chapter 8.
  28. Curry, J. K.; Byrd, J. D. J. Appl. Polym. Sci. 1965, 9, 295. https://doi.org/10.1002/app.1965.070090126
  29. Bellamy, L. J. In The Infra-red of Complex Molecules, 3rd ed.; John Wiley and Sons: New York, 1975.
  30. Armarego, W. L. F.; Perrin, D. D. In Purification of Laboratory Chemicals, 4th ed.; Butterworth-Heinemann: Oxford, 1996.

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