Journal of Integrative Natural Science (통합자연과학논문집)

The Basic Science Institute Chosun University (조선대학교 기초과학연구원)
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Synthesis and Photoluminescence of Silole Derivatives

  • Received : 2013.08.22
  • Accepted : 2013.09.23
  • Published : 2013.09.30
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Abstract

The syntheses of 9,9'-spiro-9-silabifluorene as well as 1,1-dichloro-1-silafluorene and 1,1-dimethyl-1-silafluorene through the formation of 2,2'-dibromobiphenyl have been emphasized with good yields. Their fluorescence spectra are obtained using photoluminescence spectrometer and assumed to be the precursors of the development of polymers.

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References

  1. K. L. Chan, M. J. McKiernan, C. R. Town, and A. B. Holmes," Poly (2,7-dibenzosilole): a blue light emitting polymer", J. Am. Chem. Soc., Vol. 127, pp. 7662-7663, 2005. https://doi.org/10.1021/ja0508065
  2. H. Sohn, R. R. Huddleston, D. R. Powell, and R. West, "An electroluminescent polysilole and some dichlorooligosiloles", J. Am. Chem. Soc., Vol. 121, pp. 2935-2936, 1999. https://doi.org/10.1021/ja983350i
  3. Y. Xu, T. Fujino, H. Naito, T. Dohmaru, K. Oka, H. Sohn, and R. West, "Electroluminescent properties of a novel ${\sigma}^*-{\pi}^*$ conjugated polymer, poly[1,1-(2,3,4,5-tetraphenylsilole)]", Jpn. J. Appl. Phys., Vol. 38, pp. 6915-6918, 1999. https://doi.org/10.1143/JJAP.38.6915
  4. K. Tamao, M. Uchida, T. Izumizawa, K. Furukawa, and S. Yamaguchi, "Silole derivatives as efficient electron transporting materials", J. Am. Chem. Soc., Vol. 118, pp. 11974-11975, 1996. https://doi.org/10.1021/ja962829c
  5. Y. Yamaguchi, "Design of novel ${\sigma}^*-{\pi}^*$< conjugated polysilanes", Synthetic Met., Vol. 82, pp. 149153, 1996. https://doi.org/10.1016/S0379-6779(96)03782-4
  6. S. Yamaguchi and K. Tamao, "Theoretical study of the electronic structure of 2,2'-bisilole in comparison with 1,1'-bi-1,3-cyclopentadiene: ${\sigma}^*-{\pi}^*$ conjugation and a low-lying LUMO as the origin of the unusual optical properties of 3,3',4,4'-tetraphenyl-2,2'-bisilole", Bull. Chem. Soc. Jpn., Vol. 69, pp. 2327-2334, 1996. https://doi.org/10.1246/bcsj.69.2327
  7. S. Yamaguchi, T. Endo, M. Uchida, T. Izumizawa, K. Furukawa, and K. Tamao, "Toward new materials for organic electroluminescent devices: synthesis, structures, and properties of a series of 2, 5-diaryl-3, 4-diphenylsiloles", Chem. Eur. J., Vol. 6, pp. 1683-1692, 2000. https://doi.org/10.1002/(SICI)1521-3765(20000502)6:9<1683::AID-CHEM1683>3.3.CO;2-D
  8. T. Sanji, T. Sakai, C. Kabuto, and H. Sakurai, "Silole-containing ${\sigma}$-and ${\pi}$-conjugated compounds", J. Am. Chem. Soc., Vol. 120, pp. 4552-4553, 1998. https://doi.org/10.1021/ja973252h
  9. X. H. Zhou, J. C. Yan, and J. Pei, "Synthesis and relationships between the structures and properties of monodisperse star-shaped oligofluorenes", Org. Lett., Vol. 5, pp. 3543-3546, 2003. https://doi.org/10.1021/ol035461e
  10. H. Gilman and B.J. Gaj, "Preparation and stability of some organolithium compounds in tetrahydrofuran", J. Am. Chem. Soc., Vol. 22, pp. 1165-1168, 1957.
  11. H. Gilman and R. D. Gorsich, "Cyclic organosilicon compounds. I. Synthesis of compounds containing the dibenzosilole nucleus", J. Am. Chem. Soc., Vol. 80, pp. 1883-1886, 1958. https://doi.org/10.1021/ja01541a025
  12. Y. Liu, T.C. Stringfellow, D. Ballweg, I.A. Guzei, and R. West, "Structure and chemistry of 1-silafluorenyl dianion, its derivatives, and an organosilicon diradical dianion", J. Am. Chem. Soc., Vol. 124, pp. 49-57, 2002. https://doi.org/10.1021/ja011821m