Synthesis, characterization and photophysical properties of novel 5,7-disubstituted-1,4-diazepine-2,3-dicarbonitriles

Wieczorek, Ewelina; Gierszewski, Mateusz; Popenda, Łukasz; Tykarska, Ewa; Gdaniec, Мaria; Jurga, Stefan; Sikorski, Marek; Mielcarek, Jadwiga; Piskorz, Jaroslaw; Gośliński, Tomasz

doi:10.1016/j.molstruc.2016.01.032

Cited by 8 publications

(1 citation statement)

References 29 publications

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“…In recent years, diaminomaleonitrile (DAMN) and its derivatives have been applied in the synthesis of many heterocyclic compounds, including imidazoles, pyrazines, pyrimidines, purines, azepines, pyrroles, oxazoles, nucleosides as well as porphyrazine macrocycles [1][2][3][4][5][6][7][8][9][10]. At present, after many years of research, porphyrazines (Pzs) substituted with nitrogen atoms in the β positions or having rings bound to both β,β positions form a distinct class of novel macrocycles (aminoporphyrazines), along with other porphyrazines substituted with sulphur, oxygen, alkyl or aryl residues [11][12][13][14].…”

Section: Introductionmentioning

confidence: 99%

Magnesium porphyrazine with peripheral methyl (3,5-dibromophenylmethyl)amino groups – synthesis and optical properties

Wieczorek

Piskorz

Popenda

et al. 2019

Heterocyclic Communications

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Novel magnesium(II) porphyrazine with peripheral methyl(3,5-dibromophenylmethyl)amine groups was synthesized in a multi-step procedure starting from commercially available diaminomaleonitrile. All intermediates and the final macrocycle were characterized using UV–Vis, FT-IR, MS and various NMR techniques. The absorption and emission properties of the macrocycle were evaluated in N,N-dimethylformamide, dimethyl sulfoxide, and dichloromethane. The potential photosensitizing activity was evaluated by assessing the ability of the macrocycle to generate singlet oxygen in dimethyl sulfoxide and N,N-dimethylformamide.

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Section: Introductionmentioning

confidence: 99%

Magnesium porphyrazine with peripheral methyl (3,5-dibromophenylmethyl)amino groups – synthesis and optical properties

Wieczorek

Piskorz

Popenda

et al. 2019

Heterocyclic Communications

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NMR Spectroscopic and Theoretical Studies on Tautomerism and Isomerism of Perfluoroalkyl‐Substituted 1,5‐Benzodiazepines

et al. 2020

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The tautomerism and isomerism of several ethyl 2-(4-(perfluoroalkyl)dihydro-2H-benzo(naphtho)[b] [1,4]diazepin-2-ylidene) acetates were investigated by 1 H-, 13 C-, 15 N-and 19 F-NMR spectroscopy and DFT computations. Depending on the polarity and basicity of the solvent a different behaviour was observed. In CDCl 3 , (D 6 )acetone and CD 3 CN solution two chelate hydrogen bonded tautomers, the enaminoimine and the diaminodiene, were found to exist. In the polar and more basic solvents (D 6 )DMSO and (D 7 )DMF two further species, the chelate ring-opened isomers, were detected. The ratio of the isomers is influenced by the solvents and the substituents at the chelate ring. The chelate enaminoimine is favoured in the less polar chloroform, whereas the chelate diaminodiene predominates with increasing polarity of solvents. The length of the perfluoroalkyl chain and the substituents of the phenyl ring do not influence the isomeric equilibrium as much as the chlorine atom in 4-position.

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1,4-Diazepines

Boa

McPhillie

2022

Comprehensive Heterocyclic Chemistry IV

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Synthesis, characterization and photophysical properties of novel 5,7-disubstituted-1,4-diazepine-2,3-dicarbonitriles

Cited by 8 publications

References 29 publications

Magnesium porphyrazine with peripheral methyl (3,5-dibromophenylmethyl)amino groups – synthesis and optical properties

Magnesium porphyrazine with peripheral methyl (3,5-dibromophenylmethyl)amino groups – synthesis and optical properties

NMR Spectroscopic and Theoretical Studies on Tautomerism and Isomerism of Perfluoroalkyl‐Substituted 1,5‐Benzodiazepines

1,4-Diazepines

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