| Autor: |
Konrad, Nele, Horetski, Matvey, Sihtmäe, Mariliis, Truong, Khai-Nghi, Osadchuk, Irina, Burankova, Tatsiana, Kielmann, Marc, Adamson, Jasper, Kahru, Anne, Rissanen, Kari, Senge, Mathias O., Borovkov, Victor, Aav, Riina, Kananovich, Dzmitry |
| Předmět: |
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| Zdroj: |
Chemosensors; Oct2021, Vol. 9 Issue 10, p278-278, 1p |
| Abstrakt: |
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. [ABSTRACT FROM AUTHOR] |
| Databáze: |
Complementary Index |
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