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Abstract:

The preparation, isolation and characterization by elemental analysis and 1H-NMR, 13C-NMR, and MS data of the bromo derivatives of N-substituted carbazoles, i.e., of 9-methyl-9H-carbazole (1), 9-phenyl-9H-carbazole (2), 9-benzyl-9H-carbazole (3), 2-methoxy-9-methyl-9H- carbazole (4), and of C-substituted carbazoles, i.e., of 2-(acetyloxy)-9H- carbazole (5) and 3-nitro-9H-carbazole (6), are reported, in part for the first time. As brominating reagents, N-bromosuccinimide (NBS) or NBS/silica gel in CH2Cl2, NBS in AcOH, KBrO3/KBr in EtOH doped with a catalytic amount of H2SO4, or KBrO3/KBr in AcOH were employed, and their uses were compared. Semi-empirical PM3 calculations were performed to predict the reactivity of the N-substituted and C-substituted carbazoles and of their bromo derivatives and found to verify the experimental results. The UV-absorption and fluorescence and phosphorescence emission spectra of the bromocarbazole derivatives in MeCN solution at 298 K and in a solid matrix at 77 K were compared with those of the corresponding carbazoles 1-6. The dynamic properties of the lowest excited singlet and triplet states (τf, τp, φf, and φp) were measured under the same experimental conditions. The intramolecular spin-orbital-coupling effect of the Br-atom and NO2 group on the spectroscopic data, photophysical parameters, and on the photo reactivity were also briefly analyzed. © 2006 Verlag Helvetica Chimica Acta AG.

Registro:

Documento: Artículo
Título:Synthesis and electronic spectroscopy of bromocarbazoles. Direct bromination of N- and C-substituted carbazoles by N-bromosuccinimide or a N-bromosuccinimide/silica gel system
Autor:Ponce, M.B.; Cabrerizo, F.M.; Bonesi, S.M.; Erra-Balsells, R.
Filiación:Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, 1428 - Buenos Aires, Argentina
Palabras clave:Derivatives; Fluorescence; Gels; Mass spectrometry; Nuclear magnetic resonance; Phosphorescence; Silica; Spectroscopic analysis; Bromination; Emission spectra; N-bromosuccinimide (NBS); Spin-orbital-coupling; Bromine compounds; 2 (acetyloxy) 9h carbazole; 2 methoxy 9 methyl 9h carbazole; 3 nitro 9h carbazole; 9 benzyl 9h carbazole; 9 methyl 9h carbazole; 9 phenyl 9h carbazole; bromocarbazole derivative; carbazole derivative; n bromosuccinimide; silica gel; unclassified drug; article; bromination; light absorption; nuclear magnetic resonance spectroscopy; phosphorescence; priority journal; spectroscopy
Año:2006
Volumen:89
Número:6
Página de inicio:1123
Página de fin:1139
DOI: http://dx.doi.org/10.1002/hlca.200690110
Título revista:Helvetica Chimica Acta
Título revista abreviado:Helv. Chim. Acta
ISSN:0018019X
CODEN:HCACA
CAS:n bromosuccinimide, 128-08-5, 39660-53-2; silica gel, 63231-67-4
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0018019X_v89_n6_p1123_Ponce

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Citas:

---------- APA ----------
Ponce, M.B., Cabrerizo, F.M., Bonesi, S.M. & Erra-Balsells, R. (2006) . Synthesis and electronic spectroscopy of bromocarbazoles. Direct bromination of N- and C-substituted carbazoles by N-bromosuccinimide or a N-bromosuccinimide/silica gel system. Helvetica Chimica Acta, 89(6), 1123-1139.
http://dx.doi.org/10.1002/hlca.200690110
---------- CHICAGO ----------
Ponce, M.B., Cabrerizo, F.M., Bonesi, S.M., Erra-Balsells, R. "Synthesis and electronic spectroscopy of bromocarbazoles. Direct bromination of N- and C-substituted carbazoles by N-bromosuccinimide or a N-bromosuccinimide/silica gel system" . Helvetica Chimica Acta 89, no. 6 (2006) : 1123-1139.
http://dx.doi.org/10.1002/hlca.200690110
---------- MLA ----------
Ponce, M.B., Cabrerizo, F.M., Bonesi, S.M., Erra-Balsells, R. "Synthesis and electronic spectroscopy of bromocarbazoles. Direct bromination of N- and C-substituted carbazoles by N-bromosuccinimide or a N-bromosuccinimide/silica gel system" . Helvetica Chimica Acta, vol. 89, no. 6, 2006, pp. 1123-1139.
http://dx.doi.org/10.1002/hlca.200690110
---------- VANCOUVER ----------
Ponce, M.B., Cabrerizo, F.M., Bonesi, S.M., Erra-Balsells, R. Synthesis and electronic spectroscopy of bromocarbazoles. Direct bromination of N- and C-substituted carbazoles by N-bromosuccinimide or a N-bromosuccinimide/silica gel system. Helv. Chim. Acta. 2006;89(6):1123-1139.
http://dx.doi.org/10.1002/hlca.200690110