Thiourea Organocatalysts as Emerging Chiral Pollutants: En Route to Porphyrin-Based (Chir)Optical Sensing
نویسندگان
چکیده
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 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 7.2–7.4 mg/L). The observed toxic effect was pronounced by influence trifluoromethyl moiety. En route to porphyrin-based chemosensing Takemoto-type their supramolecular binding a series zinc porphyrins studied UV-Vis circular dichroism (CD) spectroscopy, computational analysis single crystal X-ray diffraction. association constant values generally increased increasing electron-withdrawing properties electron-donating ability result predominant Zn⋯N cation–dipole (Lewis acid–base) interaction. event induced CD signal in Soret band region porphyrin hosts—a crucial property for chirality thioureas.
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ژورنال
عنوان ژورنال: Chemosensors
سال: 2021
ISSN: ['2227-9040']
DOI: https://doi.org/10.3390/chemosensors9100278