Syntheses, structures, luminescence and electrochemistry of benzene- and biphenyl-centered bis- and tris-1,3,2-diazaboroles and-1,3,2-diazaborolidines

Weber L, Domke I, Schmidt C, Braun T, Stammler H-G, Neumann B (2006)
Journal of the Chemical Society. Dalton Transactions (17): 2127-2132.

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Abstract
Reaction of 1,4-bis(dibromoboryl) benzene (1a) with 2 equiv. of the diazabutadiene (BuN)-Bu-t = CH - CH= (NBu)-Bu-t and subsequent reduction of the obtained bis(1,3,2-diazaborolium) salt 2a with sodium amalgam afforded the 1,4-bis(1,3,2-diazaborolyl) benzene 3a. Similary, 1,3-bis(dibromoboryl) benzene (1b), 1,3,5-tris(dibromoboryl) benzene (1c) and 4,4'-bis(dibromoboryl) biphenyl (1d) were converted into compounds 3b, 3c and 3d which contain two or three diazaborolyl substituents at the arene core. Treatment of precursors 1a, b, d with two equiv. or 1c with three equiv. of N,N'-di-tert-butylethane-1,2-diamine in the presence of an excess of NEt3 gave rise to the diazaborolidine derivatives 4a-4d. Reaction of 1,3-bis(diiodoboryl) benzene 1e with two equivalents of N,N'-dimethylethane-1,2-diamine in the presence of NEt3 furnished the corresponding 1,3-bis(diazaborolidinyl) benzene 4e. The novel compounds were characterized by elemental analyses and spectroscopy (H-1, C-13, B-11 NMR, MS). The molecular structures of 3c, 4a and 4e were eludicated by X-ray-diffraction analyses. In addition to this, the oxidative cyclovoltammograms and blue emission spectra of these novel compounds were discussed. Here, the electronic communication between boron heterocycles on the different spacer-units and the luminescence of the oligo-diazaborolylarenes were of interest.
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Weber L, Domke I, Schmidt C, Braun T, Stammler H-G, Neumann B. Syntheses, structures, luminescence and electrochemistry of benzene- and biphenyl-centered bis- and tris-1,3,2-diazaboroles and-1,3,2-diazaborolidines. Journal of the Chemical Society. Dalton Transactions. 2006;(17):2127-2132.
Weber, L., Domke, I., Schmidt, C., Braun, T., Stammler, H. - G., & Neumann, B. (2006). Syntheses, structures, luminescence and electrochemistry of benzene- and biphenyl-centered bis- and tris-1,3,2-diazaboroles and-1,3,2-diazaborolidines. Journal of the Chemical Society. Dalton Transactions(17), 2127-2132.
Weber, L., Domke, I., Schmidt, C., Braun, T., Stammler, H. - G., and Neumann, B. (2006). Syntheses, structures, luminescence and electrochemistry of benzene- and biphenyl-centered bis- and tris-1,3,2-diazaboroles and-1,3,2-diazaborolidines. Journal of the Chemical Society. Dalton Transactions, 2127-2132.
Weber, L., et al., 2006. Syntheses, structures, luminescence and electrochemistry of benzene- and biphenyl-centered bis- and tris-1,3,2-diazaboroles and-1,3,2-diazaborolidines. Journal of the Chemical Society. Dalton Transactions, (17), p 2127-2132.
L. Weber, et al., “Syntheses, structures, luminescence and electrochemistry of benzene- and biphenyl-centered bis- and tris-1,3,2-diazaboroles and-1,3,2-diazaborolidines”, Journal of the Chemical Society. Dalton Transactions, 2006, pp. 2127-2132.
Weber, L., Domke, I., Schmidt, C., Braun, T., Stammler, H.-G., Neumann, B.: Syntheses, structures, luminescence and electrochemistry of benzene- and biphenyl-centered bis- and tris-1,3,2-diazaboroles and-1,3,2-diazaborolidines. Journal of the Chemical Society. Dalton Transactions. 2127-2132 (2006).
Weber, Lothar, Domke, Imme, Schmidt, C., Braun, Thomas, Stammler, Hans-Georg, and Neumann, Beate. “Syntheses, structures, luminescence and electrochemistry of benzene- and biphenyl-centered bis- and tris-1,3,2-diazaboroles and-1,3,2-diazaborolidines”. Journal of the Chemical Society. Dalton Transactions 17 (2006): 2127-2132.
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Weber L, Werner V, Fox MA, Marder TB, Schwedler S, Brockhinke A, Stammler HG, Neumann B., Dalton Trans (15), 2009
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Weber L, Werner V, Domke I, Stammler HG, Neumann B., Dalton Trans (31), 2006
PMID: 16883404

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