Novel A3B-type tert-butyl-substituted tribenzodiazepinoporphyrazine: Synthesis, spectral properties and DFT study

• Novel А3В-type tribenzodiazepinoporphyrazine was synthesized and characterized.
• Aggregation was detected and studied by spectral methods.
• DFT quantum chemical calculations were carried out.
• Detailed analysis of the complicated UV/Vis spectrum of free-base tribenzodiazepinoporphyrazine was performed.

Novel A3B-type 8(9),13(14),18(19)-tri-tert-butyl-25,47-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, 1H, 13C 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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