Electrochemical Investigation of Symmetric Aminoquinones
Fuente:
Zenodo
Gespeichert in:
| Hauptverfasser: | , , , , , |
|---|---|
| Format: | Recurso digital |
| Sprache: | Englisch |
| Veröffentlicht: |
Zenodo
2024
|
| Online-Zugang: | |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| _version_ | 1866901198301298688 |
|---|---|
| author | Maier, Janine Yagmur, Reyhan Wickenhauser, Dominik Torvisco, Ana Kelterer, Anne-Marie Spirk, Stefan |
| author_facet | Maier, Janine Yagmur, Reyhan Wickenhauser, Dominik Torvisco, Ana Kelterer, Anne-Marie Spirk, Stefan |
| contents | <p>Quinones have a wide range of valuable properties and potential applications in medicinal chemistry, materials science,<br>optoelectronic devices, and batteries. Molecular redesign using different functional groups, like amines, can optimize their<br>properties and prevent undesired side reactions. However, the synthesis of aminoquinones can be particularly challenging at times,<br>and there is a need for simple and efficient routes to access these compounds without metal catalysts or halogenated starting<br>materials. Here, we demonstrate the synthesis and electrochemical characterization of a series of aminoquinones derived from<br>renewable sources, namely vanillin or 2-methoxyhydroquinone. We employ a series of primary and secondary amines, varying in<br>their electronic situation as well as steric demand. Depending on the type of starting material, either the desired aminoquinone or<br>the related Schiff-base adduct was obtained. The aminoquinones were further explored towards their stability at different pH<br>values. At extreme pH values, the deeply colored aminoquinones decompose, accompanied by decolorization of the solutions<br>within a few minutes (pH 14) or hours (pH 1). At intermediate pH values (3–8) the aminoquinones are stable upon storage in<br>solution, where they feature a quasi-reversible redox chemistry and fast, diffusion limited kinetics.</p> |
| format | Recurso digital |
| id | zenodo_https___doi_org_10_1149_1945-7111_ad8f00 |
| institution | Zenodo |
| language | eng |
| publishDate | 2024 |
| publisher | Zenodo |
| record_format | zenodo |
| spellingShingle | Electrochemical Investigation of Symmetric Aminoquinones Maier, Janine Yagmur, Reyhan Wickenhauser, Dominik Torvisco, Ana Kelterer, Anne-Marie Spirk, Stefan <p>Quinones have a wide range of valuable properties and potential applications in medicinal chemistry, materials science,<br>optoelectronic devices, and batteries. Molecular redesign using different functional groups, like amines, can optimize their<br>properties and prevent undesired side reactions. However, the synthesis of aminoquinones can be particularly challenging at times,<br>and there is a need for simple and efficient routes to access these compounds without metal catalysts or halogenated starting<br>materials. Here, we demonstrate the synthesis and electrochemical characterization of a series of aminoquinones derived from<br>renewable sources, namely vanillin or 2-methoxyhydroquinone. We employ a series of primary and secondary amines, varying in<br>their electronic situation as well as steric demand. Depending on the type of starting material, either the desired aminoquinone or<br>the related Schiff-base adduct was obtained. The aminoquinones were further explored towards their stability at different pH<br>values. At extreme pH values, the deeply colored aminoquinones decompose, accompanied by decolorization of the solutions<br>within a few minutes (pH 14) or hours (pH 1). At intermediate pH values (3–8) the aminoquinones are stable upon storage in<br>solution, where they feature a quasi-reversible redox chemistry and fast, diffusion limited kinetics.</p> |
| title | Electrochemical Investigation of Symmetric Aminoquinones |
| url | https://doi.org/10.1149/1945-7111/ad8f00 |