N-Aryl- and N-Thienylcarbazoles with Dimesitylboryl and 1,3,2-Benzodiazaborolyl Functions

Weber L, Halama J, Böhling L, Chrostowska A, Dargelos A, Stammler H-G, Neumann B (2011)
European Journal of Inorganic Chemistry 2011(20): 3091-3101.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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Abstract / Bemerkung
The reaction of the N-lithiated 3,6-di-tert-butylcarbazole with fluorodimesitylborane afforded the N-carbazolyl-functionalized dimesitylborane 1 as a colorless solid in 70% yield. [4-(3,6-Di-tert-butylcarbazol-9-yl) phenyl]dimesitylborane (2) was synthesized in 59% yield by the lithiation of N-(4-bromophenyl)-3,6-di-tert-butylcarbazole and the subsequent treatment of the organolithium compound with fluorodimesitylborane. Synthesis of yellow crystalline [5-(carbazol-9-yl)-2-thienyl]dimesitylborane 3 was effected in 66% yield by the lithiation of 3,6-di-tert-butyl-N-(2-thienyl)carbazole and the subsequent reaction with fluorodimesitylborane. Coupling of N-(4-bromophenyl)-3,6-di-tert-butylcarbazole and 2-bromo-1,3-diethyl-1,3,2-benzodiazaborole with magnesium metal in boiling THF in the presence of lithium chloride led to the formation of the functionalized benzodiazaborole 5 as a colorless solid in 68% yield. Compounds 1-3 and 5 were characterized by elemental analyses, IR and NMR spectroscopy ((1)H, (11)B, (13)C) and mass spectrometry. The molecular structures of 1 and 3 were elucidated by X-ray diffraction analyses. The 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. Thus, it was discovered that the LUMOs of 1-3 are located on the vacant 2p(z) orbital of the boron atom with contributions of the pi* orbital of the phenyl (in 2) or thiophene (in 3) unit, whereas the HOMOs are mainly represented by the carbazolyl unit.
Stichworte
Boron; Photophysics; Carbazoles; Density functional calculations
Erscheinungsjahr
2011
Zeitschriftentitel
European Journal of Inorganic Chemistry
Band
2011
Ausgabe
20
Seite(n)
3091-3101
ISSN
1434-1948
Page URI
https://pub.uni-bielefeld.de/record/2326736

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Weber L, Halama J, Böhling L, et al. N-Aryl- and N-Thienylcarbazoles with Dimesitylboryl and 1,3,2-Benzodiazaborolyl Functions. European Journal of Inorganic Chemistry. 2011;2011(20):3091-3101.
Weber, L., Halama, J., Böhling, L., Chrostowska, A., Dargelos, A., Stammler, H. - G., & Neumann, B. (2011). N-Aryl- and N-Thienylcarbazoles with Dimesitylboryl and 1,3,2-Benzodiazaborolyl Functions. European Journal of Inorganic Chemistry, 2011(20), 3091-3101. doi:10.1002/ejic.201100123
Weber, L., Halama, J., Böhling, L., Chrostowska, A., Dargelos, A., Stammler, H. - G., and Neumann, B. (2011). N-Aryl- and N-Thienylcarbazoles with Dimesitylboryl and 1,3,2-Benzodiazaborolyl Functions. European Journal of Inorganic Chemistry 2011, 3091-3101.
Weber, L., et al., 2011. N-Aryl- and N-Thienylcarbazoles with Dimesitylboryl and 1,3,2-Benzodiazaborolyl Functions. European Journal of Inorganic Chemistry, 2011(20), p 3091-3101.
L. Weber, et al., “N-Aryl- and N-Thienylcarbazoles with Dimesitylboryl and 1,3,2-Benzodiazaborolyl Functions”, European Journal of Inorganic Chemistry, vol. 2011, 2011, pp. 3091-3101.
Weber, L., Halama, J., Böhling, L., Chrostowska, A., Dargelos, A., Stammler, H.-G., Neumann, B.: N-Aryl- and N-Thienylcarbazoles with Dimesitylboryl and 1,3,2-Benzodiazaborolyl Functions. European Journal of Inorganic Chemistry. 2011, 3091-3101 (2011).
Weber, Lothar, Halama, Johannes, Böhling, Lena, Chrostowska, Anna, Dargelos, Alain, Stammler, Hans-Georg, and Neumann, Beate. “N-Aryl- and N-Thienylcarbazoles with Dimesitylboryl and 1,3,2-Benzodiazaborolyl Functions”. European Journal of Inorganic Chemistry 2011.20 (2011): 3091-3101.