Synthesis and Luminescent Properties of <i>s</i>-Tetrazine Derivatives Conjugated with the 4<i>H</i>-1,2,4-Triazole Ring
New derivatives obtained by the combination of unique 1,2,4,5-tetrazine and 4<i>H</i>-1,2,4-triazole rings have great application potential in many fields. Therefore, two synthetic few-step methodologies, which make use of commercially available 4-cyanobenzoic acid (method A) and ethyl d...
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| Format: | Article |
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MDPI AG
2022-06-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/11/3642 |
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| author | Anna Maj Agnieszka Kudelko Marcin Świątkowski |
| author_facet | Anna Maj Agnieszka Kudelko Marcin Świątkowski |
| author_sort | Anna Maj |
| collection | DOAJ |
| description | New derivatives obtained by the combination of unique 1,2,4,5-tetrazine and 4<i>H</i>-1,2,4-triazole rings have great application potential in many fields. Therefore, two synthetic few-step methodologies, which make use of commercially available 4-cyanobenzoic acid (method A) and ethyl diazoacetate (method B), were applied to produce two groups of the aforementioned heterocyclic conjugates. In both cases, the target compounds were obtained in various combinations, by introducing electron-donating or electron-withdrawing substituents into the terminal rings, together with aromatic or aliphatic substituents on the triazole nitrogen atom. Synthesis of such designed systems made it possible to analyze the influence of individual elements of the structure on the reaction course, as well as the absorption and emission properties. The structure of all products was confirmed by conventional spectroscopic methods, and their luminescent properties were also determined. |
| first_indexed | 2024-03-10T01:02:50Z |
| format | Article |
| id | doaj.art-bdfca589d45440af8f38df058260a256 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T01:02:50Z |
| publishDate | 2022-06-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-bdfca589d45440af8f38df058260a2562023-11-23T14:32:04ZengMDPI AGMolecules1420-30492022-06-012711364210.3390/molecules27113642Synthesis and Luminescent Properties of <i>s</i>-Tetrazine Derivatives Conjugated with the 4<i>H</i>-1,2,4-Triazole RingAnna Maj0Agnieszka Kudelko1Marcin Świątkowski2Department 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, PolandInstitute of General and Ecological Chemistry, Lodz University of Technology, Zeromskiego 116, PL-90924 Lodz, PolandNew derivatives obtained by the combination of unique 1,2,4,5-tetrazine and 4<i>H</i>-1,2,4-triazole rings have great application potential in many fields. Therefore, two synthetic few-step methodologies, which make use of commercially available 4-cyanobenzoic acid (method A) and ethyl diazoacetate (method B), were applied to produce two groups of the aforementioned heterocyclic conjugates. In both cases, the target compounds were obtained in various combinations, by introducing electron-donating or electron-withdrawing substituents into the terminal rings, together with aromatic or aliphatic substituents on the triazole nitrogen atom. Synthesis of such designed systems made it possible to analyze the influence of individual elements of the structure on the reaction course, as well as the absorption and emission properties. The structure of all products was confirmed by conventional spectroscopic methods, and their luminescent properties were also determined.https://www.mdpi.com/1420-3049/27/11/3642<i>s</i>-tetrazine4<i>H</i>-1,2,4-triazolepinner reaction |
| spellingShingle | Anna Maj Agnieszka Kudelko Marcin Świątkowski Synthesis and Luminescent Properties of <i>s</i>-Tetrazine Derivatives Conjugated with the 4<i>H</i>-1,2,4-Triazole Ring Molecules <i>s</i>-tetrazine 4<i>H</i>-1,2,4-triazole pinner reaction |
| title | Synthesis and Luminescent Properties of <i>s</i>-Tetrazine Derivatives Conjugated with the 4<i>H</i>-1,2,4-Triazole Ring |
| title_full | Synthesis and Luminescent Properties of <i>s</i>-Tetrazine Derivatives Conjugated with the 4<i>H</i>-1,2,4-Triazole Ring |
| title_fullStr | Synthesis and Luminescent Properties of <i>s</i>-Tetrazine Derivatives Conjugated with the 4<i>H</i>-1,2,4-Triazole Ring |
| title_full_unstemmed | Synthesis and Luminescent Properties of <i>s</i>-Tetrazine Derivatives Conjugated with the 4<i>H</i>-1,2,4-Triazole Ring |
| title_short | Synthesis and Luminescent Properties of <i>s</i>-Tetrazine Derivatives Conjugated with the 4<i>H</i>-1,2,4-Triazole Ring |
| title_sort | synthesis and luminescent properties of i s i tetrazine derivatives conjugated with the 4 i h i 1 2 4 triazole ring |
| topic | <i>s</i>-tetrazine 4<i>H</i>-1,2,4-triazole pinner reaction |
| url | https://www.mdpi.com/1420-3049/27/11/3642 |
| work_keys_str_mv | AT annamaj synthesisandluminescentpropertiesofisitetrazinederivativesconjugatedwiththe4ihi124triazolering AT agnieszkakudelko synthesisandluminescentpropertiesofisitetrazinederivativesconjugatedwiththe4ihi124triazolering AT marcinswiatkowski synthesisandluminescentpropertiesofisitetrazinederivativesconjugatedwiththe4ihi124triazolering |