1,3,2-Benzodiazaboroles with 1,3-Pentafluorophenyl and Tetrafluoropyridyl Substituents as Building Blocks in Luminescent Compounds

Weber L, Halama J, Böhling L, Brockhinke A, Chrostowska A, Darrigan C, Dargelos A, Stammler H-G, Neumann B (2013)
European Journal of Inorganic Chemistry 2013(24): 4268-4279.

Journal Article | Published | English

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Abstract
The reaction of N-4-trimethylsilylphenyl-3,6-di-tert-butylcarbazole (3) or N-5-trimethylsilylthien-2-yl-3,6-di-tert-butylcarbazole (4) with boron tribromide and subsequently with triphenylphosphane afforded the dibromoborylphenylcarbazole-phosphane adduct 5 or its thiophene derivative 6 as colorless solids. These adducts were converted into the new benzodiazaborole derivatives 7 and 8 by treatment with N,N-bis(pentafluorophenyl)-o-phenylenediamine (1) and 2,2,6,6-tetramethylpiperidine in hot toluene (52 or 45% yield). The analogous compounds 9 and 10 were obtained by condensing precursors 5 and 6 with bis(N,N-2,3,5,6-tetrafluoropyrid-4-yl)-o-phenylenediamine (2) in the presence of the piperidine derivative in 35 and 16% yield. Compounds 7-10 were characterized by NMR spectroscopy (H-1, B-11, C-13, F-19) and mass spectrometry. The molecular structure of 8 was elucidated by X-ray diffraction analysis. The borylated systems show intense blue luminescence upon UV irradiation.
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Weber L, Halama J, Böhling L, et al. 1,3,2-Benzodiazaboroles with 1,3-Pentafluorophenyl and Tetrafluoropyridyl Substituents as Building Blocks in Luminescent Compounds. European Journal of Inorganic Chemistry. 2013;2013(24):4268-4279.
Weber, L., Halama, J., Böhling, L., Brockhinke, A., Chrostowska, A., Darrigan, C., Dargelos, A., et al. (2013). 1,3,2-Benzodiazaboroles with 1,3-Pentafluorophenyl and Tetrafluoropyridyl Substituents as Building Blocks in Luminescent Compounds. European Journal of Inorganic Chemistry, 2013(24), 4268-4279.
Weber, L., Halama, J., Böhling, L., Brockhinke, A., Chrostowska, A., Darrigan, C., Dargelos, A., Stammler, H. - G., and Neumann, B. (2013). 1,3,2-Benzodiazaboroles with 1,3-Pentafluorophenyl and Tetrafluoropyridyl Substituents as Building Blocks in Luminescent Compounds. European Journal of Inorganic Chemistry 2013, 4268-4279.
Weber, L., et al., 2013. 1,3,2-Benzodiazaboroles with 1,3-Pentafluorophenyl and Tetrafluoropyridyl Substituents as Building Blocks in Luminescent Compounds. European Journal of Inorganic Chemistry, 2013(24), p 4268-4279.
L. Weber, et al., “1,3,2-Benzodiazaboroles with 1,3-Pentafluorophenyl and Tetrafluoropyridyl Substituents as Building Blocks in Luminescent Compounds”, European Journal of Inorganic Chemistry, vol. 2013, 2013, pp. 4268-4279.
Weber, L., Halama, J., Böhling, L., Brockhinke, A., Chrostowska, A., Darrigan, C., Dargelos, A., Stammler, H.-G., Neumann, B.: 1,3,2-Benzodiazaboroles with 1,3-Pentafluorophenyl and Tetrafluoropyridyl Substituents as Building Blocks in Luminescent Compounds. European Journal of Inorganic Chemistry. 2013, 4268-4279 (2013).
Weber, Lothar, Halama, Johannes, Böhling, Lena, Brockhinke, Andreas, Chrostowska, Anna, Darrigan, Clovis, Dargelos, Alain, Stammler, Hans-Georg, and Neumann, Beate. “1,3,2-Benzodiazaboroles with 1,3-Pentafluorophenyl and Tetrafluoropyridyl Substituents as Building Blocks in Luminescent Compounds”. European Journal of Inorganic Chemistry 2013.24 (2013): 4268-4279.
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