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.

Download
Es wurde kein Volltext hochgeladen. Nur Publikationsnachweis!
Zeitschriftenaufsatz | Veröffentlicht | Englisch
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.
Erscheinungsjahr
Zeitschriftentitel
European Journal of Inorganic Chemistry
Band
2011
Zeitschriftennummer
20
Seite
3091-3101
ISSN
PUB-ID

Zitieren

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.