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Novel A₃B-type tert-butyl-substituted tribenzodiazepinoporphyrazine: synthesis, spectral properties and DFT study
Pavel A Tarakanov1, Anton O Simakov2, Alexandr Yu Tolbin1
1Institute of Physiologically Active Compounds, Russian Academy of Sciences, 1 Severny Proezd, 142432 Chernogolovka, Moscow Region, Russian Federation.
Abstract:
Novel A3B-type 8(9),13(14),18(19)-tri-tert-butyl-2(5),4(7)-bis(4-tert-butylphenyl)tribenzo[g,l,q]-6H-1,4-diazepino[2,3-b]porphyrazine, which has high solubility in organic solvents, was obtained by template co-condensation of 2,3-dicyano-5,7-bis(4-tert-butylphenyl)-6H-1,4-diazepine and 4-tert-butylphthalonitrile. It was characterized by UV/Vis, (1)H, (13)C NMR spectroscopy, and MALDI-TOF/TOF mass spectrometry. We have demonstrated for the first time using fluorescence spectroscopy measurements and quantum-chemical calculations that the complicated UV/Vis spectrum of A3B-type tribenzodiazepinoporphyrazine is due to the formation of stable H-type aggregates.
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