Heterocyclic Schiff Bases of 3-Aminobenzanthrone and Their Reduced Analogues: Synthesis, Properties and Spectroscopy
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 whic...
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MDPI AG
2021-04-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/26/9/2570 |
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| author | Natalja Orlova Irena Nikolajeva Aleksandrs Pučkins Sergey Belyakov Elena Kirilova |
| author_facet | Natalja Orlova Irena Nikolajeva Aleksandrs Pučkins Sergey Belyakov Elena Kirilova |
| author_sort | Natalja Orlova |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-03-10T11:53:16Z |
| format | Article |
| id | doaj.art-a330609e19a44a1f9138528593c1cc15 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T11:53:16Z |
| publishDate | 2021-04-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-a330609e19a44a1f9138528593c1cc152023-11-21T17:34:34ZengMDPI AGMolecules1420-30492021-04-01269257010.3390/molecules26092570Heterocyclic Schiff Bases of 3-Aminobenzanthrone and Their Reduced Analogues: Synthesis, Properties and SpectroscopyNatalja Orlova0Irena Nikolajeva1Aleksandrs Pučkins2Sergey Belyakov3Elena Kirilova4Laboratory of Physical Organic Chemistry, Latvian Institute of Organic Synthesis, LV-1006 Riga, LatviaDepartment of Applied Chemistry, Institute of Life Sciences and Technology, Daugavpils University, LV-5401 Daugavpils, LatviaDepartment of Applied Chemistry, Institute of Life Sciences and Technology, Daugavpils University, LV-5401 Daugavpils, LatviaLaboratory of Physical Organic Chemistry, Latvian Institute of Organic Synthesis, LV-1006 Riga, LatviaDepartment of Applied Chemistry, Institute of Life Sciences and Technology, Daugavpils University, LV-5401 Daugavpils, LatviaNew 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.https://www.mdpi.com/1420-3049/26/9/2570Schiff basesbenzanthroneheterocyclesreductionfluorescence spectroscopy |
| spellingShingle | Natalja Orlova Irena Nikolajeva Aleksandrs Pučkins Sergey Belyakov Elena Kirilova Heterocyclic Schiff Bases of 3-Aminobenzanthrone and Their Reduced Analogues: Synthesis, Properties and Spectroscopy Molecules Schiff bases benzanthrone heterocycles reduction fluorescence spectroscopy |
| title | Heterocyclic Schiff Bases of 3-Aminobenzanthrone and Their Reduced Analogues: Synthesis, Properties and Spectroscopy |
| title_full | Heterocyclic Schiff Bases of 3-Aminobenzanthrone and Their Reduced Analogues: Synthesis, Properties and Spectroscopy |
| title_fullStr | Heterocyclic Schiff Bases of 3-Aminobenzanthrone and Their Reduced Analogues: Synthesis, Properties and Spectroscopy |
| title_full_unstemmed | Heterocyclic Schiff Bases of 3-Aminobenzanthrone and Their Reduced Analogues: Synthesis, Properties and Spectroscopy |
| title_short | Heterocyclic Schiff Bases of 3-Aminobenzanthrone and Their Reduced Analogues: Synthesis, Properties and Spectroscopy |
| title_sort | heterocyclic schiff bases of 3 aminobenzanthrone and their reduced analogues synthesis properties and spectroscopy |
| topic | Schiff bases benzanthrone heterocycles reduction fluorescence spectroscopy |
| url | https://www.mdpi.com/1420-3049/26/9/2570 |
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