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

Pavel A Tarakanov; Anton O Simakov; Alexandr Yu Tolbin; Irina O Balashova; Vladimir I Shestov; Larisa G Tomilova

doi:10.1016/j.saa.2014.12.054

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

Spectrochim Acta A Mol Biomol Spectrosc. 2015 Mar 15:139:464-70. doi: 10.1016/j.saa.2014.12.054. Epub 2014 Dec 25.

Authors

Pavel A Tarakanov¹, Anton O Simakov², Alexandr Yu Tolbin³, Irina O Balashova³, Vladimir I Shestov³, Larisa G Tomilova⁴

Affiliations

¹ Institute of Physiologically Active Compounds, Russian Academy of Sciences, 1 Severny Proezd, 142432 Chernogolovka, Moscow Region, Russian Federation. Electronic address: paveltar369@gmail.com.
² Centre for Theoretical and Computational Chemistry (CTCC), Department of Chemistry, University of Oslo, P.O. Box 1033 Blindern, N-0315 Oslo, Norway.
³ Institute of Physiologically Active Compounds, Russian Academy of Sciences, 1 Severny Proezd, 142432 Chernogolovka, Moscow Region, Russian Federation.
⁴ 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.

PMID: 25576944
DOI: 10.1016/j.saa.2014.12.054

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.

Keywords: Aggregation; Diazepine; Intermolecular interaction; Porphyrazine; Synthesis.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Benzodiazepines / chemical synthesis*
Benzodiazepines / chemistry*
Carbon-13 Magnetic Resonance Spectroscopy
Models, Molecular*
Porphyrins / chemical synthesis*
Porphyrins / chemistry*
Proton Magnetic Resonance Spectroscopy
Quantum Theory*
Spectrometry, Fluorescence
Spectrophotometry, Ultraviolet
Thermodynamics

Substances

Porphyrins
Benzodiazepines