Heterocyclic Schiff Bases of 3-Aminobenzanthrone and Their Reduced Analogues: Synthesis, Properties and Spectroscopy
| Autor: | Sergey Belyakov, Irena Nikolajeva, Natalja Orlova, Elena Kirilova, Aleksandrs Pučkins |
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| Rok vydání: | 2021 |
| Předmět: |
heterocycles
Chemistry Organic Chemistry Pharmaceutical Science reduction fluorescence spectroscopy Condensation reaction Article Fluorescence spectroscopy Benzanthrone Analytical Chemistry Sodium borohydride chemistry.chemical_compound QD241-441 Chemistry (miscellaneous) Drug Discovery Polymer chemistry benzanthrone Molecular Medicine Schiff bases Physical and Theoretical Chemistry Solvent effects Spectroscopy Luminescence Single crystal |
| Zdroj: | Molecules Volume 26 Issue 9 Molecules, Vol 26, Iss 2570, p 2570 (2021) |
| ISSN: | 1420-3049 |
| Popis: | New substituted azomethines of benzanthrone with heterocyclic substituents were synthesized by condensation reaction of 3-aminobenzo[de]anthracen-7-one with appropriate aromatic aldehydes. The resulting imines were reduced with sodium borohydride to the corresponding amines, the luminescence of which is more pronounced in comparison with the initial azomethines. The novel benzanthrone derivatives were characterized by NMR, IR, MS, UV/Vis, and fluorescence spectroscopy. The structure of three dyes was studied by the X-ray single crystal structure analysis. The solvent effect on photophysical behaviors of synthesized imines and amines was investigated. The obtained compounds absorb at 420–525 nm, have relatively large Stokes shifts (up to 150 nm in ethanol), and emit at 500–660 nm. The results testify that emission of the studied compounds is sensitive to the solvent polarity, exhibiting negative fluorosolvatochromism for the synthesized azomethines and positive fluorosolvatochromism for the obtained amines. The results obtained indicate that the synthesized compounds are promising as luminescent dyes. |
| Databáze: | OpenAIRE |
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