Synthesis and electronic spectroscopy of bromocarbazoles. Direct bromination of N- and C-substituted carbazoles by N-bromosuccinimide or a N-bromosuccinimide/silica gel system
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-substi...
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todo:paper_0018019X_v89_n6_p1123_Ponce2023-10-03T14:15:09Z Synthesis and electronic spectroscopy of bromocarbazoles. Direct bromination of N- and C-substituted carbazoles by N-bromosuccinimide or a N-bromosuccinimide/silica gel system Ponce, M.B. Cabrerizo, F.M. Bonesi, S.M. Erra-Balsells, R. 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 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. Fil:Bonesi, S.M. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Erra-Balsells, R. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_0018019X_v89_n6_p1123_Ponce |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
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 |
| spellingShingle |
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 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 |
| topic_facet |
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 |
| description |
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. |
| format |
JOUR |
| author |
Ponce, M.B. Cabrerizo, F.M. Bonesi, S.M. Erra-Balsells, R. |
| author_facet |
Ponce, M.B. Cabrerizo, F.M. Bonesi, S.M. Erra-Balsells, R. |
| author_sort |
Ponce, M.B. |
| title |
Synthesis and electronic spectroscopy of bromocarbazoles. Direct bromination of N- and C-substituted carbazoles by N-bromosuccinimide or a N-bromosuccinimide/silica gel system |
| title_short |
Synthesis and electronic spectroscopy of bromocarbazoles. Direct bromination of N- and C-substituted carbazoles by N-bromosuccinimide or a N-bromosuccinimide/silica gel system |
| title_full |
Synthesis and electronic spectroscopy of bromocarbazoles. Direct bromination of N- and C-substituted carbazoles by N-bromosuccinimide or a N-bromosuccinimide/silica gel system |
| title_fullStr |
Synthesis and electronic spectroscopy of bromocarbazoles. Direct bromination of N- and C-substituted carbazoles by N-bromosuccinimide or a N-bromosuccinimide/silica gel system |
| title_full_unstemmed |
Synthesis and electronic spectroscopy of bromocarbazoles. Direct bromination of N- and C-substituted carbazoles by N-bromosuccinimide or a N-bromosuccinimide/silica gel system |
| title_sort |
synthesis and electronic spectroscopy of bromocarbazoles. direct bromination of n- and c-substituted carbazoles by n-bromosuccinimide or a n-bromosuccinimide/silica gel system |
| url |
http://hdl.handle.net/20.500.12110/paper_0018019X_v89_n6_p1123_Ponce |
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