Synthetic, structural, photophysical and computational studies on 2-arylethynyl-1,3,2-diazaboroles

Weber L, Werner V, Fox MA, Marder TB, Schwedler S, Brockhinke A, Stammler H-G, Neumann B (2009)
Journal of the Chemical Society. Dalton Transactions (15): 2823-2831.

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Abstract
New 2-arylalkynyl benzo-1,3,2-diazaboroles,2-(4'-XC6H4C C)-1,3-Et-2-1,3,2-N2BC6H4(X= Me 2; MeO 3; MeS 4; Me2N 5), were prepared from B-bromodiazaborole, 2-Br-1,3-Et-2-1,3,2-N2BC6H4, with the appropriate lithiated arylacetylene, ArC CLi. Molecular structures of 2, 3 and 5 were determined by X-ray diffraction studies. UV-vis and luminescence spectroscopic studies on these diazaboroles reveal intense blue/violet fluorescence with very large quantum yields of 0.89-0.99 for 2-5. The experimental findings were complemented by DFT and TD-DFT calculations. The Stokes shift of only 2600 cm(-1) for 5, compared to Stokes shifts in the range of 5900-7300 cm(-1) for 1-4, is partly explained by the different electronic structures found in 5 compared to 1-4 (X = H). The HOMO is mainly located on the aryl group in 5 and on the diazaborolyl group in 1-4 whereas the LUMOs are largely aryl in character for all compounds. Thus, in contrast to other conjugated systems containing three-coordinate boron centers such as B(Mes)(2), (Mes=2,4,6-Me3C6H2), in which the boron serves as a pi-acceptor, the 10-pi electron benzodiazaborole moiety appears to function as a pi-donor moiety.
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Weber L, Werner V, Fox MA, et al. Synthetic, structural, photophysical and computational studies on 2-arylethynyl-1,3,2-diazaboroles. Journal of the Chemical Society. Dalton Transactions. 2009;(15):2823-2831.
Weber, L., Werner, V., Fox, M. A., Marder, T. B., Schwedler, S., Brockhinke, A., Stammler, H. - G., et al. (2009). Synthetic, structural, photophysical and computational studies on 2-arylethynyl-1,3,2-diazaboroles. Journal of the Chemical Society. Dalton Transactions(15), 2823-2831.
Weber, L., Werner, V., Fox, M. A., Marder, T. B., Schwedler, S., Brockhinke, A., Stammler, H. - G., and Neumann, B. (2009). Synthetic, structural, photophysical and computational studies on 2-arylethynyl-1,3,2-diazaboroles. Journal of the Chemical Society. Dalton Transactions, 2823-2831.
Weber, L., et al., 2009. Synthetic, structural, photophysical and computational studies on 2-arylethynyl-1,3,2-diazaboroles. Journal of the Chemical Society. Dalton Transactions, (15), p 2823-2831.
L. Weber, et al., “Synthetic, structural, photophysical and computational studies on 2-arylethynyl-1,3,2-diazaboroles”, Journal of the Chemical Society. Dalton Transactions, 2009, pp. 2823-2831.
Weber, L., Werner, V., Fox, M.A., Marder, T.B., Schwedler, S., Brockhinke, A., Stammler, H.-G., Neumann, B.: Synthetic, structural, photophysical and computational studies on 2-arylethynyl-1,3,2-diazaboroles. Journal of the Chemical Society. Dalton Transactions. 2823-2831 (2009).
Weber, Lothar, Werner, Vanessa, Fox, Mark A., Marder, Todd B., Schwedler, Stefanie, Brockhinke, Andreas, Stammler, Hans-Georg, and Neumann, Beate. “Synthetic, structural, photophysical and computational studies on 2-arylethynyl-1,3,2-diazaboroles”. Journal of the Chemical Society. Dalton Transactions 15 (2009): 2823-2831.
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