Thiourea Organocatalysts as Emerging Chiral Pollutants: En Route to Porphyrin-Based (Chir)Optical Sensing
| Autor: | Kari Rissanen, Anne Kahru, Mathias O. Senge, Dzmitry G. Kananovich, Jasper Adamson, Mariliis Sihtmäe, Khai-Nghi Truong, Marc Kielmann, Irina Osadchuk, Riina Aav, Tatsiana Burankova, Nele Konrad, Victor V. Borovkov, Matvey Horetski |
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| Přispěvatelé: | Tallinn University of Technology (TTÜ), Belarusian State University, National Institute of Chemical Physics and Biophysics = Keemilise ja bioloogilise füüsika instituut [Estonie] (NICPB | KBFI), University of Jyväskylä (JYU), Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier (ICGM), Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Centre National de la Recherche Scientifique (CNRS), Trinity College Dublin, University of Dublin, This work was supported by the Estonian Research Council grant PUTJD749 (for I.O.) PRG399, (for N.K., R.A., V.B.), PSG400 (for J.A), PRG749 (for M.S.), European Regional Development Fund grants NAMUR+ 2014-2020.4.01.16-0123 (for M.S. and A.K) and TK134 (for A.K., J.A.) and the European Union’s H2020-FETOPEN grant 828779 (INITIO) (for N.K., K.-N.T., K.R., M.K., M.O.S., D.K., R.A., V.B.). M.H. is grateful to the Dora Plus program for financial support of his research stay at Tallinn University of Technology., European Project: 828779,INITIO, Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier (ICGM ICMMM), Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Centre National de la Recherche Scientifique (CNRS)-Université de Montpellier (UM)-Université Montpellier 1 (UM1)-Université Montpellier 2 - Sciences et Techniques (UM2)-Institut de Chimie du CNRS (INC) |
| Jazyk: | angličtina |
| Rok vydání: | 2021 |
| Předmět: |
Circular dichroism
Supramolecular chemistry chirality monitorointi Environmental pollution chiral amine Vibrio fischeri QD415-436 010402 general chemistry Biochemistry 01 natural sciences Medicinal chemistry supramolecular chemistry bakteerit Analytical Chemistry chemistry.chemical_compound katalyytit rikkiyhdisteet supramolekulaarinen kemia Moiety [CHIM]Chemical Sciences [CHIM.COOR]Chemical Sciences/Coordination chemistry Physical and Theoretical Chemistry thiourea orgaaniset yhdisteet chiral pollutants Trifluoromethyl 010405 organic chemistry toxicity host–guest binding Porphyrin 0104 chemical sciences Takemoto’s catalyst circular dichroism ekotoksikologia chemistry Thiourea 13. Climate action [SDV.TOX.ECO]Life Sciences [q-bio]/Toxicology/Ecotoxicology [SDE.BE]Environmental Sciences/Biodiversity and Ecology Chirality (chemistry) porphyrin organocatalyst |
| Zdroj: | Chemosensors Chemosensors, 2021, 9 (10), pp.278. ⟨10.3390/chemosensors9100278⟩ Chemosensors, MDPI, 2021, 9 (10), pp.278. ⟨10.3390/chemosensors9100278⟩ Volume 9 Issue 10 Chemosensors, Vol 9, Iss 278, p 278 (2021) |
| ISSN: | 2227-9040 |
| 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: | OpenAIRE |
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