title: Novel A₃B-type tert-butyl-substituted tribenzodiazepinoporphyrazine: synthesis, spectral properties and DFT study.
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.
authors.affiliation: Institute of Physiologically Active Compounds, Russian Academy of Sciences, 1 Severny Proezd, 142432 Chernogolovka, Moscow Region, Russian Federation. Electronic address: paveltar369@gmail.com.
authors.forename: Pavel A
authors.initials: PA
authors.lastname: Tarakanov
authors.affiliation: Centre for Theoretical and Computational Chemistry (CTCC), Department of Chemistry, University of Oslo, P.O. Box 1033 Blindern, N-0315 Oslo, Norway.
authors.forename: Anton O
authors.initials: AO
authors.lastname: Simakov
authors.affiliation: Institute of Physiologically Active Compounds, Russian Academy of Sciences, 1 Severny Proezd, 142432 Chernogolovka, Moscow Region, Russian Federation.
authors.forename: Alexandr Yu
authors.initials: AY
authors.lastname: Tolbin
authors.affiliation: Institute of Physiologically Active Compounds, Russian Academy of Sciences, 1 Severny Proezd, 142432 Chernogolovka, Moscow Region, Russian Federation.
authors.forename: Irina O
authors.initials: IO
authors.lastname: Balashova
authors.affiliation: Institute of Physiologically Active Compounds, Russian Academy of Sciences, 1 Severny Proezd, 142432 Chernogolovka, Moscow Region, Russian Federation.
authors.forename: Vladimir I
authors.initials: VI
authors.lastname: Shestov
authors.affiliation: Institute of Physiologically Active Compounds, Russian Academy of Sciences, 1 Severny Proezd, 142432 Chernogolovka, Moscow Region, Russian Federation; Department of Chemistry, M.V. Lomonosov Moscow State University, 1 Leninskie Gory, 119991 Moscow, Russian Federation. Electronic address: tom@org.chem.msu.ru.
authors.forename: Larisa G
authors.initials: LG
authors.lastname: Tomilova
mesh_terms: D001569:Benzodiazepines / Q000138:chemical synthesis* / Q000737:chemistry*; D066241:Carbon-13 Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D011166:Porphyrins / Q000138:chemical synthesis* / Q000737:chemistry*; D066244:Proton Magnetic Resonance Spectroscopy; D011789:Quantum Theory; D013050:Spectrometry, Fluorescence; D013056:Spectrophotometry, Ultraviolet; D013816:Thermodynamics
chemical_list: D011166:Porphyrins; D001569:Benzodiazepines
keywords: Aggregation; Diazepine; Intermolecular interaction; Porphyrazine; Synthesis