dc.contributor.author | Konrad, Nele | |
dc.contributor.author | Horetski, Matvey | |
dc.contributor.author | Sihtmäe, Mariliis | |
dc.contributor.author | Truong, Khai-Nghi | |
dc.contributor.author | Osadchuk, Irina | |
dc.contributor.author | Burankova, Tatsiana | |
dc.contributor.author | Kielmann, Marc | |
dc.contributor.author | Adamson, Jasper | |
dc.contributor.author | Kahru, Anne | |
dc.contributor.author | Rissanen, Kari | |
dc.contributor.author | Senge, Mathias O. | |
dc.contributor.author | Borovkov, Victor | |
dc.contributor.author | Aav, Riina | |
dc.contributor.author | Kananovich, Dzmitry | |
dc.date.accessioned | 2021-11-11T09:54:35Z | |
dc.date.available | 2021-11-11T09:54:35Z | |
dc.date.issued | 2021 | |
dc.identifier.citation | Konrad, N., Horetski, M., Sihtmäe, M., Truong, K.-N., Osadchuk, I., Burankova, T., Kielmann, M., Adamson, J., Kahru, A., Rissanen, K., Senge, M. O., Borovkov, V., Aav, R., & Kananovich, D. (2021). Thiourea Organocatalysts as Emerging Chiral Pollutants : En Route to Porphyrin-Based (Chir)Optical Sensing. <i>Chemosensors</i>, <i>9</i>(10), Article 278. <a href="https://doi.org/10.3390/chemosensors9100278" target="_blank">https://doi.org/10.3390/chemosensors9100278</a> | |
dc.identifier.other | CONVID_101862001 | |
dc.identifier.uri | https://jyx.jyu.fi/handle/123456789/78613 | |
dc.description.abstract | 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. | en |
dc.format.mimetype | application/pdf | |
dc.language.iso | eng | |
dc.publisher | MDPI AG | |
dc.relation.ispartofseries | Chemosensors | |
dc.rights | CC BY 4.0 | |
dc.subject.other | porphyrin | |
dc.subject.other | thiourea | |
dc.subject.other | chiral amine | |
dc.subject.other | organocatalyst | |
dc.subject.other | Takemoto’s catalyst | |
dc.subject.other | host–guest binding | |
dc.subject.other | chirality | |
dc.subject.other | supramolecular chemistry | |
dc.subject.other | circular dichroism | |
dc.subject.other | toxicity | |
dc.subject.other | chiral pollutants | |
dc.subject.other | Vibrio fischeri | |
dc.title | Thiourea Organocatalysts as Emerging Chiral Pollutants : En Route to Porphyrin-Based (Chir)Optical Sensing | |
dc.type | research article | |
dc.identifier.urn | URN:NBN:fi:jyu-202111115631 | |
dc.contributor.laitos | Kemian laitos | fi |
dc.contributor.laitos | Department of Chemistry | en |
dc.contributor.oppiaine | Orgaaninen kemia | fi |
dc.contributor.oppiaine | Organic Chemistry | en |
dc.type.uri | http://purl.org/eprint/type/JournalArticle | |
dc.type.coar | http://purl.org/coar/resource_type/c_2df8fbb1 | |
dc.description.reviewstatus | peerReviewed | |
dc.relation.issn | 2227-9040 | |
dc.relation.numberinseries | 10 | |
dc.relation.volume | 9 | |
dc.type.version | publishedVersion | |
dc.rights.copyright | © 2021 by the authors. Licensee MDPI, Basel, Switzerland. | |
dc.rights.accesslevel | openAccess | fi |
dc.type.publication | article | |
dc.relation.grantnumber | 828779 | |
dc.relation.grantnumber | 828779 | |
dc.relation.projectid | info:eu-repo/grantAgreement/EC/H2020/828779/EU//INITIO | |
dc.subject.yso | monitorointi | |
dc.subject.yso | rikkiyhdisteet | |
dc.subject.yso | bakteerit | |
dc.subject.yso | katalyytit | |
dc.subject.yso | orgaaniset yhdisteet | |
dc.subject.yso | supramolekulaarinen kemia | |
dc.subject.yso | ekotoksikologia | |
dc.format.content | fulltext | |
jyx.subject.uri | http://www.yso.fi/onto/yso/p3628 | |
jyx.subject.uri | http://www.yso.fi/onto/yso/p5731 | |
jyx.subject.uri | http://www.yso.fi/onto/yso/p1749 | |
jyx.subject.uri | http://www.yso.fi/onto/yso/p15480 | |
jyx.subject.uri | http://www.yso.fi/onto/yso/p3841 | |
jyx.subject.uri | http://www.yso.fi/onto/yso/p37759 | |
jyx.subject.uri | http://www.yso.fi/onto/yso/p19671 | |
dc.rights.url | https://creativecommons.org/licenses/by/4.0/ | |
dc.relation.doi | 10.3390/chemosensors9100278 | |
dc.relation.funder | European Commission | en |
dc.relation.funder | Euroopan komissio | fi |
jyx.fundingprogram | FET Future and Emerging Technologies, H2020 | en |
jyx.fundingprogram | FET Future and Emerging Technologies, H2020 | fi |
jyx.fundinginformation | 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. | |
dc.type.okm | A1 | |