1,3,4-Thiadiazole-Containing Azo Dyes: Synthesis, Spectroscopic Properties and Molecular Structure
Three series of azo dyes derived from 2-amino-5-aryl-1,3,4-thiadiazoles and aniline, <i>N,N</i>-dimethylaniline and phenol were synthesized in high yields by a conventional diazotization-coupling sequence. The chemical structures of the prepared compounds were confirmed by <sup>1&l...
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| Format: | Article |
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MDPI AG
2020-06-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/25/12/2822 |
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| author | Agnieszka Kudelko Monika Olesiejuk Marcin Luczynski Marcin Swiatkowski Tomasz Sieranski Rafal Kruszynski |
| author_facet | Agnieszka Kudelko Monika Olesiejuk Marcin Luczynski Marcin Swiatkowski Tomasz Sieranski Rafal Kruszynski |
| author_sort | Agnieszka Kudelko |
| collection | DOAJ |
| description | Three series of azo dyes derived from 2-amino-5-aryl-1,3,4-thiadiazoles and aniline, <i>N,N</i>-dimethylaniline and phenol were synthesized in high yields by a conventional diazotization-coupling sequence. The chemical structures of the prepared compounds were confirmed by <sup>1</sup>H-NMR, <sup>13</sup>C-NMR, IR, UV-Vis spectroscopy, mass spectrometry and elemental analysis. In addition, the X-ray single crystal structure of a representative azo dye was presented. For explicit determination of the influence of a substituent on radiation absorption in UV-Vis range, time-dependent density functional theory calculations were performed. |
| first_indexed | 2024-03-10T19:03:05Z |
| format | Article |
| id | doaj.art-4861e41042de476d8f1d49642d1b8a2a |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T19:03:05Z |
| publishDate | 2020-06-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-4861e41042de476d8f1d49642d1b8a2a2023-11-20T04:16:10ZengMDPI AGMolecules1420-30492020-06-012512282210.3390/molecules251228221,3,4-Thiadiazole-Containing Azo Dyes: Synthesis, Spectroscopic Properties and Molecular StructureAgnieszka Kudelko0Monika Olesiejuk1Marcin Luczynski2Marcin Swiatkowski3Tomasz Sieranski4Rafal Kruszynski5Department of Chemical Organic Technology and Petrochemistry, The Silesian University of Technology, Krzywoustego 4, PL-44100 Gliwice, PolandDepartment of Chemical Organic Technology and Petrochemistry, The Silesian University of Technology, Krzywoustego 4, PL-44100 Gliwice, PolandDepartment of Chemical Organic Technology and Petrochemistry, The Silesian University of Technology, Krzywoustego 4, PL-44100 Gliwice, PolandDepartment of X-ray Crystallography and Crystal Chemistry, Institute of General and Ecological Chemistry, Lodz University of Technology, Żeromskiego 116, PL-90924 Łódź, PolandDepartment of X-ray Crystallography and Crystal Chemistry, Institute of General and Ecological Chemistry, Lodz University of Technology, Żeromskiego 116, PL-90924 Łódź, PolandDepartment of X-ray Crystallography and Crystal Chemistry, Institute of General and Ecological Chemistry, Lodz University of Technology, Żeromskiego 116, PL-90924 Łódź, PolandThree series of azo dyes derived from 2-amino-5-aryl-1,3,4-thiadiazoles and aniline, <i>N,N</i>-dimethylaniline and phenol were synthesized in high yields by a conventional diazotization-coupling sequence. The chemical structures of the prepared compounds were confirmed by <sup>1</sup>H-NMR, <sup>13</sup>C-NMR, IR, UV-Vis spectroscopy, mass spectrometry and elemental analysis. In addition, the X-ray single crystal structure of a representative azo dye was presented. For explicit determination of the influence of a substituent on radiation absorption in UV-Vis range, time-dependent density functional theory calculations were performed.https://www.mdpi.com/1420-3049/25/12/2822heterocycles2-arylazo-5-aryl-1,3,4-thiadiazolesazo-coupling reactionscrystal structure |
| spellingShingle | Agnieszka Kudelko Monika Olesiejuk Marcin Luczynski Marcin Swiatkowski Tomasz Sieranski Rafal Kruszynski 1,3,4-Thiadiazole-Containing Azo Dyes: Synthesis, Spectroscopic Properties and Molecular Structure Molecules heterocycles 2-arylazo-5-aryl-1,3,4-thiadiazoles azo-coupling reactions crystal structure |
| title | 1,3,4-Thiadiazole-Containing Azo Dyes: Synthesis, Spectroscopic Properties and Molecular Structure |
| title_full | 1,3,4-Thiadiazole-Containing Azo Dyes: Synthesis, Spectroscopic Properties and Molecular Structure |
| title_fullStr | 1,3,4-Thiadiazole-Containing Azo Dyes: Synthesis, Spectroscopic Properties and Molecular Structure |
| title_full_unstemmed | 1,3,4-Thiadiazole-Containing Azo Dyes: Synthesis, Spectroscopic Properties and Molecular Structure |
| title_short | 1,3,4-Thiadiazole-Containing Azo Dyes: Synthesis, Spectroscopic Properties and Molecular Structure |
| title_sort | 1 3 4 thiadiazole containing azo dyes synthesis spectroscopic properties and molecular structure |
| topic | heterocycles 2-arylazo-5-aryl-1,3,4-thiadiazoles azo-coupling reactions crystal structure |
| url | https://www.mdpi.com/1420-3049/25/12/2822 |
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