1,3,2-Diazaborolyl-functionalized thiophenes and dithiophenes: synthesis, structure, electrochemistry and luminescence

Weber L, Werner V, Domke I, Stammler H-G, Neumann B (2006)
Journal of the Chemical Society. Dalton Transactions (31): 3777-3784.

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Reaction of 2-bromo-1,3-diethyl-1,3,2-benzodiazaborole (1) with equimolar amounts of thienyl lithium or 2,2'-dithienyl lithium led to the generation of benzodiazaboroles 2 and 3 which are functionalized at the boron atom by a 2-thienyl or a 5-(2,2'-dithienyl) unit. Similarly 2-bromo-1,3-diethyl-1,3,2-naphthodiazaborole (4) and thienyl lithium or 2,2'-dithienyl lithium afforded the naphthoborolyl-substituted thiophene 5 or dithiophene 6. Treatment of 2,5-bis(dibromoboryl)-thiophene 7 with 2 eq. of tBuN=CH-CH=NtBu in n-hexane followed by sodium amalgam reduction of the obtained bis(diazaborolium) salt 8 gave the 2,5- bis(diazaborolyl) thiophene 9. The 2,5-bis(diazaborolidinyl)-thiophene 10 resulted from the cyclocondensation of 7 with 2 eq. of N, N'-di-tert-butylethylenediamine in the presence of NEt3. Analogously, cyclocondensation of 7 with N, N'-diethylphenylenediamine gave the bis(benzodiazaborolyl) functionalized thiophene 11. The novel compounds were characterized by elemental analysis and spectroscopy (H-1-, B-11-, C-13-NMR, MS and UV-VIS). The molecular structure of 3 was elucidated by X-ray diffraction. Cyclovoltammograms show an irreversible oxidation wave at 298-598 vs. Fc/Fc(+). The borolylated thiophenes and dithienyls show intense blue luminescence with Stokes shifts of 30-107 nm.
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Weber L, Werner V, Domke I, Stammler H-G, Neumann B. 1,3,2-Diazaborolyl-functionalized thiophenes and dithiophenes: synthesis, structure, electrochemistry and luminescence. Journal of the Chemical Society. Dalton Transactions. 2006;(31):3777-3784.
Weber, L., Werner, V., Domke, I., Stammler, H. - G., & Neumann, B. (2006). 1,3,2-Diazaborolyl-functionalized thiophenes and dithiophenes: synthesis, structure, electrochemistry and luminescence. Journal of the Chemical Society. Dalton Transactions(31), 3777-3784.
Weber, L., Werner, V., Domke, I., Stammler, H. - G., and Neumann, B. (2006). 1,3,2-Diazaborolyl-functionalized thiophenes and dithiophenes: synthesis, structure, electrochemistry and luminescence. Journal of the Chemical Society. Dalton Transactions, 3777-3784.
Weber, L., et al., 2006. 1,3,2-Diazaborolyl-functionalized thiophenes and dithiophenes: synthesis, structure, electrochemistry and luminescence. Journal of the Chemical Society. Dalton Transactions, (31), p 3777-3784.
L. Weber, et al., “1,3,2-Diazaborolyl-functionalized thiophenes and dithiophenes: synthesis, structure, electrochemistry and luminescence”, Journal of the Chemical Society. Dalton Transactions, 2006, pp. 3777-3784.
Weber, L., Werner, V., Domke, I., Stammler, H.-G., Neumann, B.: 1,3,2-Diazaborolyl-functionalized thiophenes and dithiophenes: synthesis, structure, electrochemistry and luminescence. Journal of the Chemical Society. Dalton Transactions. 3777-3784 (2006).
Weber, Lothar, Werner, Vanessa, Domke, Imme, Stammler, Hans-Georg, and Neumann, Beate. “1,3,2-Diazaborolyl-functionalized thiophenes and dithiophenes: synthesis, structure, electrochemistry and luminescence”. Journal of the Chemical Society. Dalton Transactions 31 (2006): 3777-3784.
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Synthetic, structural, photophysical and computational studies of pi-conjugated bis- and tris-1,3,2-benzodiazaboroles and related bis(boryl) dithiophenes.
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