| Autor: |
Nele Konrad, Matvey Horetski, Mariliis Sihtmäe, Khai-Nghi Truong, Irina Osadchuk, Tatsiana Burankova, Marc Kielmann, Jasper Adamson, Anne Kahru, Kari Rissanen, Mathias O. Senge, Victor Borovkov, Riina Aav, Dzmitry Kananovich |
| Jazyk: |
angličtina |
| Rok vydání: |
2021 |
| Předmět: |
|
| Zdroj: |
Chemosensors, Vol 9, Iss 10, p 278 (2021) |
| Druh dokumentu: |
article |
| ISSN: |
2227-9040 |
| DOI: |
10.3390/chemosensors9100278 |
| Popis: |
Environmental pollution with chiral organic compounds is an emerging problem requiring innovative sensing methods. Amino-functionalized thioureas, such as 2-(dimethylamino)cyclohexyl-(3,5-bis(trifluoromethyl)phenyl)thiourea (Takemoto’s catalyst), are widely used organocatalysts with virtually unknown environmental safety data. Ecotoxicity studies based on the Vibrio fischeri luminescence inhibition test reveal significant toxicity of Takemoto’s catalyst (EC50 = 7.9 mg/L) and its NH2-substituted analog (EC50 = 7.2–7.4 mg/L). The observed toxic effect was pronounced by the influence of the trifluoromethyl moiety. En route to the porphyrin-based chemosensing of Takemoto-type thioureas, their supramolecular binding to a series of zinc porphyrins was studied with UV-Vis and circular dichroism (CD) spectroscopy, computational analysis and single crystal X-ray diffraction. The association constant values generally increased with the increasing electron-withdrawing properties of the porphyrins and electron-donating ability of the thioureas, a result of the predominant Zn⋯N cation–dipole (Lewis acid–base) interaction. The binding event induced a CD signal in the Soret band region of the porphyrin hosts—a crucial property for chirality sensing of Takemoto-type thioureas. |
| Databáze: |
Directory of Open Access Journals |
| Externí odkaz: |
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