Synthesis and Properties of New 3-Heterylamino-Substituted 9-Nitrobenzanthrone Derivatives
In the present study, new fluorophores based on disubstituted benzanthrone derivatives were designed starting from 9-nitro-3-bromobenzanthrone with nucleophilic substitution of the bromine atom with some secondary cyclic amines. It has been found that this reaction is positively affected by the pres...
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MDPI AG
2023-07-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/28/13/5171 |
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| author | Armands Maļeckis Marija Cvetinska Aleksandrs Puckins Sergejs Osipovs Jelizaveta Sirokova Sergey Belyakov Elena Kirilova |
| author_facet | Armands Maļeckis Marija Cvetinska Aleksandrs Puckins Sergejs Osipovs Jelizaveta Sirokova Sergey Belyakov Elena Kirilova |
| author_sort | Armands Maļeckis |
| collection | DOAJ |
| description | In the present study, new fluorophores based on disubstituted benzanthrone derivatives were designed starting from 9-nitro-3-bromobenzanthrone with nucleophilic substitution of the bromine atom with some secondary cyclic amines. It has been found that this reaction is positively affected by the presence of a nitro group in comparison with 3-bromobenzanthrone. The new compounds exhibit intense absorption and pronounced luminescent properties in various organic solvents. In this regard, their photophysical properties were evaluated with an experimental study of the solvatochromic behavior of the obtained compounds in various solvents. It has recently been found that the addition of an electron-withdrawing nitro group to the benzanthrone core increases its first- and second-order hyperpolarizability. Such dyes can be used in the fabrication of optical limiter devices. Therefore, the developed fluorescent molecules have a potential prospect for extensive application in optoelectronics. |
| first_indexed | 2024-03-11T01:33:42Z |
| format | Article |
| id | doaj.art-df63fba7516c4a2db81c4de2a5701f31 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-11T01:33:42Z |
| publishDate | 2023-07-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-df63fba7516c4a2db81c4de2a5701f312023-11-18T17:09:14ZengMDPI AGMolecules1420-30492023-07-012813517110.3390/molecules28135171Synthesis and Properties of New 3-Heterylamino-Substituted 9-Nitrobenzanthrone DerivativesArmands Maļeckis0Marija Cvetinska1Aleksandrs Puckins2Sergejs Osipovs3Jelizaveta Sirokova4Sergey Belyakov5Elena Kirilova6Institute of Technology of Organic Chemistry, Faculty of Materials Science and Applied Chemistry, Riga Technical University, P. Valdena Str. 3, LV-1048 Riga, LatviaInstitute of Technology of Organic Chemistry, Faculty of Materials Science and Applied Chemistry, Riga Technical University, P. Valdena Str. 3, LV-1048 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, LatviaDepartment of Applied Chemistry, Institute of Life Sciences and Technology, Daugavpils University, LV-5401 Daugavpils, LatviaLatvian Institute of Organic Synthesis, Aizkraukles Str. 21, LV-1006 Riga, LatviaDepartment of Applied Chemistry, Institute of Life Sciences and Technology, Daugavpils University, LV-5401 Daugavpils, LatviaIn the present study, new fluorophores based on disubstituted benzanthrone derivatives were designed starting from 9-nitro-3-bromobenzanthrone with nucleophilic substitution of the bromine atom with some secondary cyclic amines. It has been found that this reaction is positively affected by the presence of a nitro group in comparison with 3-bromobenzanthrone. The new compounds exhibit intense absorption and pronounced luminescent properties in various organic solvents. In this regard, their photophysical properties were evaluated with an experimental study of the solvatochromic behavior of the obtained compounds in various solvents. It has recently been found that the addition of an electron-withdrawing nitro group to the benzanthrone core increases its first- and second-order hyperpolarizability. Such dyes can be used in the fabrication of optical limiter devices. Therefore, the developed fluorescent molecules have a potential prospect for extensive application in optoelectronics.https://www.mdpi.com/1420-3049/28/13/5171benzanthroneheterocyclesubstituted aminesnitro derivativefluorescencesolvatochromism |
| spellingShingle | Armands Maļeckis Marija Cvetinska Aleksandrs Puckins Sergejs Osipovs Jelizaveta Sirokova Sergey Belyakov Elena Kirilova Synthesis and Properties of New 3-Heterylamino-Substituted 9-Nitrobenzanthrone Derivatives Molecules benzanthrone heterocycle substituted amines nitro derivative fluorescence solvatochromism |
| title | Synthesis and Properties of New 3-Heterylamino-Substituted 9-Nitrobenzanthrone Derivatives |
| title_full | Synthesis and Properties of New 3-Heterylamino-Substituted 9-Nitrobenzanthrone Derivatives |
| title_fullStr | Synthesis and Properties of New 3-Heterylamino-Substituted 9-Nitrobenzanthrone Derivatives |
| title_full_unstemmed | Synthesis and Properties of New 3-Heterylamino-Substituted 9-Nitrobenzanthrone Derivatives |
| title_short | Synthesis and Properties of New 3-Heterylamino-Substituted 9-Nitrobenzanthrone Derivatives |
| title_sort | synthesis and properties of new 3 heterylamino substituted 9 nitrobenzanthrone derivatives |
| topic | benzanthrone heterocycle substituted amines nitro derivative fluorescence solvatochromism |
| url | https://www.mdpi.com/1420-3049/28/13/5171 |
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