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Synthesis and Photoelectronic Properties of Thermally Stable Poly[oxy(2,7-fluoren-9-onenylene)oxy(diorganosilylene)]s

  • Received : 2012.02.28
  • Accepted : 2012.04.17
  • Published : 2012.06.20

Abstract

Melt copolymerization reactions of several bis(diethylamino)silane derivatives, bis(diethylamino)methylphenylsilane, bis(diethylamino)methyloctylsilane, 1,2-bis(diethylamino)tetramethyldisilane, and 1,3-bis(diethylamino) tetramethyldisiloxane, with 2,7-dihydroxyfluoren-9-one were carried out to yield poly[oxy(2,7-fluoren- 9-onenylene)oxy(diorganosilylene)]s bearing the fluoren-9-one fluorescent aromatic group in the polymer main chain: poly[oxy(2,7-fluoren-9-onenylene)oxy(methylphenylsilylene)], poly[oxy(2,7-fluoren-9-onenylene) oxy(methyloctylsilylene)], poly[oxy(2,7-fluoren-9-onenylene)oxy(tetramethyldisilylene)], and poly[oxy- (2,7-fluoren-9-onenylene)oxy(tetramethyldisiloxanylene)]. These polymeric materials are soluble in common organic solvents such as $CHCl_3$ and THF. FTIR spectra of all the materials reveal characteristic Si-O-C stretching frequencies at 1012-1018 $cm^{-1}$. In the THF solution, the prepared materials show strong maximum absorption peaks at 258-270 nm, strong maximum excitation peaks at 260-280 nm, and strong maximum fluorescence emission bands at 310-420 nm. TGA thermograms suggest that most of the polymers are essentially stable to $200^{\circ}C$ without any weight loss and up to $300^{\circ}C$ with only a weight loss of less than 5% in nitrogen.

Keywords

References

  1. Yamamoto, T. Bull. Chem. Soc. Jpn. 2010, 83, 431. https://doi.org/10.1246/bcsj.20090338
  2. Chen, J.; Cao, Y. Macromol. Rapid Commun. 2007, 28, 1714. https://doi.org/10.1002/marc.200700326
  3. Jenekhe, S. A. Chem. Mater. 2004, 16, 4381. https://doi.org/10.1021/cm041000r
  4. Clarson, S. J.; Semlyen, J. A. In Siloxane Polymers; PTR Prentice Hall, Inc.: Englewood Cliffs, New Jersey, 1993.
  5. Bao, Z. Adv. Mater. 2000, 12, 227. https://doi.org/10.1002/(SICI)1521-4095(200002)12:3<227::AID-ADMA227>3.0.CO;2-U
  6. Barashkov, N. N.; Gunder, O. A. In Fluorescent Polymers; Ellis Horwood: London, UK, 1994.
  7. 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
  8. Toulokhonova, I.; Bjerke-Kroll, B.; West, R. J. Organomet. Chem. 2003, 686, 101. https://doi.org/10.1016/S0022-328X(03)00672-7
  9. Keller, T. D.; Homrighausen, C. L. J. Polym. Sci., Part A: Polym. Chem. 2002, 40, 88. https://doi.org/10.1002/pola.10091
  10. Xu, C.; Wakamiya, A.; Yamaguchi, S. J. Am. Chem. Soc. 2005, 127, 1638. https://doi.org/10.1021/ja042964m
  11. Chandrasekhar, V. In Inorganic and Organometallic Polymers; Springer-Verlag: Berlin, 2005.
  12. Rubinsztajn, S.; Cella, J. A. Macromolecules 2005, 38, 1061. https://doi.org/10.1021/ma047984n
  13. Cai, G.; Weber, W. P. Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 2001, 42(1), 171.
  14. Nguyen, K.-A. T.; Shamshurin, A.; Clarke, S.; Matisons, J. Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 2004, 45(1), 706.
  15. 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
  16. Lee, J. H.; Park, Y. T. Bull. Korean Chem. Soc. 2004, 25, 889. https://doi.org/10.5012/bkcs.2004.25.6.889
  17. Kim, M. H.; Park, Y. T. Bull. Korean Chem. Soc. 2005, 26, 488. https://doi.org/10.5012/bkcs.2005.26.3.488
  18. 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
  19. Kim, J. H.; Park, Y. T. Bull. Korean Chem. Soc. 2006, 27, 869. https://doi.org/10.5012/bkcs.2006.27.6.869
  20. 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
  21. 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
  22. Grisorio, R.; Allegretta, G.; Mastrorilli, P.; Suranna, G. P. Macromolecules 2011, 44, 7977. https://doi.org/10.1021/ma2015003
  23. Thomas, J.; Christenson, C. W.; Blanche, P.-A.; Yamamoto, M.; Norwood, R. A.; Peyghambarian, N. Chem. Mater. 2011, 23, 416. https://doi.org/10.1021/cm102144h
  24. Jin, J.-K.; Choi, J.-K.; Kim, B.-J.; Kang, H.-B.; Yoon, S.-C.; You, H.; Jung, H.-T. Macromolecules 2011, 44, 502. https://doi.org/10.1021/ma102173a
  25. Demadrille, R.; Rannou, P.; Bleuse, J.; Oddou, J.-L.; Pron, A. Macromolecules 2003, 36, 7045. https://doi.org/10.1021/ma030171z
  26. Mukherjee, I.; Drake, K.; Berke-Schlessel, D.; Lelkes, P. I.; Yeh, J.-M.; Wei, Y. Macromolecules 2010, 43, 3277. https://doi.org/10.1021/ma902798b
  27. Yun, S. B.; Park, Y. T. Bull. Korean Chem. Soc. 2008, 29, 2373.
  28. Jung, I. K.; Park, Y. T. Bull. Korean Chem. Soc. 2011, 32, 1303. https://doi.org/10.5012/bkcs.2011.32.4.1303
  29. Krieble, R. H.; Burkhard, C. A. J. Am. Chem. Soc. 1947, 69, 2689. https://doi.org/10.1021/ja01203a040
  30. Padmanaban, M.; Kakimoto, M.; Imai, Y. J. Polym. Sci. Part A: Polym. Chem. 1990, 28, 2997. https://doi.org/10.1002/pola.1990.080281109
  31. Pretsch, E.; Buhlmann, P.; Affolter, C. In Structure Determination of Organic Compounds, Tables of Spectral Data, 3rd ed.; Springer- Verlag: Berlin, 2000.
  32. Williams, E. A. NMR Spectroscopy of Organosilicon Compounds, In The Chemistry of Organic Silicon Compunds; Patai, S.; Rappoport, Z., Eds.; Wiley: Chichester, UK, 1989; Vol. 1, Chapter 8.
  33. Curry, J. K.; Byrd, J. D. J. Appl. Polym. Sci. 1965, 9, 295. https://doi.org/10.1002/app.1965.070090126
  34. Bellamy, L. J. In The Infra-red of Complex Molecules, 3rd ed.; John Wiley and Sons: New York, 1975.
  35. Armarego, W. L. F.; Perrin, D. D. In Purification of Laboratory Chemicals, 4th ed.; Butterworth-Heinemann: Oxford, 1996.

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