Synthetic, Structural, Photophysical and Computational Studies on π-Conjugated 1,3,2-Benzodiazaboroles with Carbazole Building Blocks

Weber L, Halama J, Werner V, Hanke K, Böhling L, Chrostowska A, Dargelos A, Maciejczyk M, Raza A-L, Stammler H-G, Neumann B (2010)
European Journal of Inorganic Chemistry 2010(34): 5416-5425.

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Abstract
The reaction of the N-lithiated 3,6-di-tert-butyl-carbazole (2) with 2-bromo-1,3-diethyl-1,3,2-benzodiazaborole (1a) and 2-bromo-1,3-diphenyl-1,3,2-benzodiazaborole (1b) afforded the 2-N-carbazolyl-functionalized benzodiazaboroles 3a and 3b as colourless solids in 77 and 73% yield, respectively. Synthesis of 2[5'-N-carbazolyl-2'-thienyl]-1,3-diethyl-1,3,2-benzodiazaborole (5a) was effected by lithiation of N-(2-thienyl)carbazole (4) and subsequent reaction with equimolar amounts of 1a, and 5a was obtained in 68% yield. Similarly, 2[5'-N-carbazolyl-2'-thienyl]-1,3-diphenyl-1,3,2-benzodiazaborole (5b) was prepared from lithiated 4 and 1b in 62% yield. Compounds 3a,b and 5a,b are characterized by elemental analyses, IR and NMR spectroscopy (H-1, B-11, C-13) and mass spectrometry. The molecular structures of 3a and 5a were elucidated by X-ray diffraction analysis. These borylated systems show intense blue luminescence. The spectroscopic results were reproduced by TD-DFT calculations at the [B3LYP/6-311G (d,p)] level of theory.
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Weber L, Halama J, Werner V, et al. Synthetic, Structural, Photophysical and Computational Studies on π-Conjugated 1,3,2-Benzodiazaboroles with Carbazole Building Blocks. European Journal of Inorganic Chemistry. 2010;2010(34):5416-5425.
Weber, L., Halama, J., Werner, V., Hanke, K., Böhling, L., Chrostowska, A., Dargelos, A., et al. (2010). Synthetic, Structural, Photophysical and Computational Studies on π-Conjugated 1,3,2-Benzodiazaboroles with Carbazole Building Blocks. European Journal of Inorganic Chemistry, 2010(34), 5416-5425.
Weber, L., Halama, J., Werner, V., Hanke, K., Böhling, L., Chrostowska, A., Dargelos, A., Maciejczyk, M., Raza, A. - L., Stammler, H. - G., et al. (2010). Synthetic, Structural, Photophysical and Computational Studies on π-Conjugated 1,3,2-Benzodiazaboroles with Carbazole Building Blocks. European Journal of Inorganic Chemistry 2010, 5416-5425.
Weber, L., et al., 2010. Synthetic, Structural, Photophysical and Computational Studies on π-Conjugated 1,3,2-Benzodiazaboroles with Carbazole Building Blocks. European Journal of Inorganic Chemistry, 2010(34), p 5416-5425.
L. Weber, et al., “Synthetic, Structural, Photophysical and Computational Studies on π-Conjugated 1,3,2-Benzodiazaboroles with Carbazole Building Blocks”, European Journal of Inorganic Chemistry, vol. 2010, 2010, pp. 5416-5425.
Weber, L., Halama, J., Werner, V., Hanke, K., Böhling, L., Chrostowska, A., Dargelos, A., Maciejczyk, M., Raza, A.-L., Stammler, H.-G., Neumann, B.: Synthetic, Structural, Photophysical and Computational Studies on π-Conjugated 1,3,2-Benzodiazaboroles with Carbazole Building Blocks. European Journal of Inorganic Chemistry. 2010, 5416-5425 (2010).
Weber, Lothar, Halama, Johannes, Werner, Vanessa, Hanke, Kenny, Böhling, Lena, Chrostowska, Anna, Dargelos, Alain, Maciejczyk, Malgorzata, Raza, Anna-Lena, Stammler, Hans-Georg, and Neumann, Beate. “Synthetic, Structural, Photophysical and Computational Studies on π-Conjugated 1,3,2-Benzodiazaboroles with Carbazole Building Blocks”. European Journal of Inorganic Chemistry 2010.34 (2010): 5416-5425.
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