Push-Pull Structures Based on 2-Aryl/thienyl Substituted Quinazolin-4(3<i>H</i>)-ones and 4-Cyanoquinazolines
Design and synthesis of 2-(aryl/thiophen-2-yl)quinazolin-4(3<i>H</i>)-ones and 4-cyano-2-arylquinazolines with Et<sub>2</sub>N-, Ph<sub>2</sub>N- or carbazol-9-yl- electron donating fragment are described. The key photophysical properties of these compounds have b...
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| Format: | Article |
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MDPI AG
2022-10-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/21/7156 |
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| author | Tatyana N. Moshkina Emiliya V. Nosova Julia V. Permyakova Galina N. Lipunova Ekaterina F. Zhilina Grigory A. Kim Pavel A. Slepukhin Valery N. Charushin |
| author_facet | Tatyana N. Moshkina Emiliya V. Nosova Julia V. Permyakova Galina N. Lipunova Ekaterina F. Zhilina Grigory A. Kim Pavel A. Slepukhin Valery N. Charushin |
| author_sort | Tatyana N. Moshkina |
| collection | DOAJ |
| description | Design and synthesis of 2-(aryl/thiophen-2-yl)quinazolin-4(3<i>H</i>)-ones and 4-cyano-2-arylquinazolines with Et<sub>2</sub>N-, Ph<sub>2</sub>N- or carbazol-9-yl- electron donating fragment are described. The key photophysical properties of these compounds have been studied by UV/Vis absorption and fluorescence spectroscopy in solvents of different polarity (toluene and MeCN). 2-(Aryl/thiophen-2-yl)quinazolin-4(3<i>H</i>)-ones show fluorescence in blue-green region in toluene solution with quantum yields up to 89% in the case of 2-(4’-N,N-diphenylamino[1,1’-biphenyl]-4-yl)-quinazolin-4(3<i>H</i>)-one. Moreover, triphenylamino derivative based on quinazolin-4(3<i>H</i>)-one with <i>para</i>-phenylene linker displays the highest quantum yield of 40% in powder. The fluorescence QY of Et<sub>2</sub>N and Ph<sub>2</sub>N derivatives decrease when going from toluene to MeCN solution, whereas carbazol-9-yl counterparts demonstrate strengthening of intensity that emphasizes the strong influence of donor fragment nature on photophysical properties. 4-Cyanoquinazolines are less emissive in both solvents, as well as, in solid state. The introduction of cyano group into position 4 leads to orange/red colored powder and dual emission bands. Some molecules demonstrate the increase in emission intensity upon addition of water to MeCN solution. According to frontier molecular orbitals (HOMO, LUMO) calculations, the energy gap of 4-cyanoquinazoline decreases by more than 1 eV compared to quinazolin-4-one, that is consistent with experimental data. |
| first_indexed | 2024-03-09T18:49:09Z |
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| id | doaj.art-a098ecdd0221469b827be5fd6644967b |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T18:49:09Z |
| publishDate | 2022-10-01 |
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| series | Molecules |
| spelling | doaj.art-a098ecdd0221469b827be5fd6644967b2023-11-24T05:59:33ZengMDPI AGMolecules1420-30492022-10-012721715610.3390/molecules27217156Push-Pull Structures Based on 2-Aryl/thienyl Substituted Quinazolin-4(3<i>H</i>)-ones and 4-CyanoquinazolinesTatyana N. Moshkina0Emiliya V. Nosova1Julia V. Permyakova2Galina N. Lipunova3Ekaterina F. Zhilina4Grigory A. Kim5Pavel A. Slepukhin6Valery N. Charushin7Department of Organic and Biomolecular Chemistry, Chemical Engineering Institute, Ural Federal University, Mira St. 19, 620002 Ekaterinburg, RussiaDepartment of Organic and Biomolecular Chemistry, Chemical Engineering Institute, Ural Federal University, Mira St. 19, 620002 Ekaterinburg, RussiaDepartment of Organic and Biomolecular Chemistry, Chemical Engineering Institute, Ural Federal University, Mira St. 19, 620002 Ekaterinburg, RussiaI. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, S. Kovalevskaya Str., 22, 620108 Ekaterinburg, RussiaI. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, S. Kovalevskaya Str., 22, 620108 Ekaterinburg, RussiaDepartment of Organic and Biomolecular Chemistry, Chemical Engineering Institute, Ural Federal University, Mira St. 19, 620002 Ekaterinburg, RussiaDepartment of Organic and Biomolecular Chemistry, Chemical Engineering Institute, Ural Federal University, Mira St. 19, 620002 Ekaterinburg, RussiaDepartment of Organic and Biomolecular Chemistry, Chemical Engineering Institute, Ural Federal University, Mira St. 19, 620002 Ekaterinburg, RussiaDesign and synthesis of 2-(aryl/thiophen-2-yl)quinazolin-4(3<i>H</i>)-ones and 4-cyano-2-arylquinazolines with Et<sub>2</sub>N-, Ph<sub>2</sub>N- or carbazol-9-yl- electron donating fragment are described. The key photophysical properties of these compounds have been studied by UV/Vis absorption and fluorescence spectroscopy in solvents of different polarity (toluene and MeCN). 2-(Aryl/thiophen-2-yl)quinazolin-4(3<i>H</i>)-ones show fluorescence in blue-green region in toluene solution with quantum yields up to 89% in the case of 2-(4’-N,N-diphenylamino[1,1’-biphenyl]-4-yl)-quinazolin-4(3<i>H</i>)-one. Moreover, triphenylamino derivative based on quinazolin-4(3<i>H</i>)-one with <i>para</i>-phenylene linker displays the highest quantum yield of 40% in powder. The fluorescence QY of Et<sub>2</sub>N and Ph<sub>2</sub>N derivatives decrease when going from toluene to MeCN solution, whereas carbazol-9-yl counterparts demonstrate strengthening of intensity that emphasizes the strong influence of donor fragment nature on photophysical properties. 4-Cyanoquinazolines are less emissive in both solvents, as well as, in solid state. The introduction of cyano group into position 4 leads to orange/red colored powder and dual emission bands. Some molecules demonstrate the increase in emission intensity upon addition of water to MeCN solution. According to frontier molecular orbitals (HOMO, LUMO) calculations, the energy gap of 4-cyanoquinazoline decreases by more than 1 eV compared to quinazolin-4-one, that is consistent with experimental data.https://www.mdpi.com/1420-3049/27/21/7156quinazolin-4(3<i>H</i>)-one4-cyanoquinazoline2-(biphenyl)quinazoline2-thienylquinazolineπ-linkerfluorescence |
| spellingShingle | Tatyana N. Moshkina Emiliya V. Nosova Julia V. Permyakova Galina N. Lipunova Ekaterina F. Zhilina Grigory A. Kim Pavel A. Slepukhin Valery N. Charushin Push-Pull Structures Based on 2-Aryl/thienyl Substituted Quinazolin-4(3<i>H</i>)-ones and 4-Cyanoquinazolines Molecules quinazolin-4(3<i>H</i>)-one 4-cyanoquinazoline 2-(biphenyl)quinazoline 2-thienylquinazoline π-linker fluorescence |
| title | Push-Pull Structures Based on 2-Aryl/thienyl Substituted Quinazolin-4(3<i>H</i>)-ones and 4-Cyanoquinazolines |
| title_full | Push-Pull Structures Based on 2-Aryl/thienyl Substituted Quinazolin-4(3<i>H</i>)-ones and 4-Cyanoquinazolines |
| title_fullStr | Push-Pull Structures Based on 2-Aryl/thienyl Substituted Quinazolin-4(3<i>H</i>)-ones and 4-Cyanoquinazolines |
| title_full_unstemmed | Push-Pull Structures Based on 2-Aryl/thienyl Substituted Quinazolin-4(3<i>H</i>)-ones and 4-Cyanoquinazolines |
| title_short | Push-Pull Structures Based on 2-Aryl/thienyl Substituted Quinazolin-4(3<i>H</i>)-ones and 4-Cyanoquinazolines |
| title_sort | push pull structures based on 2 aryl thienyl substituted quinazolin 4 3 i h i ones and 4 cyanoquinazolines |
| topic | quinazolin-4(3<i>H</i>)-one 4-cyanoquinazoline 2-(biphenyl)quinazoline 2-thienylquinazoline π-linker fluorescence |
| url | https://www.mdpi.com/1420-3049/27/21/7156 |
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