A1 Alkuperäisartikkeli tieteellisessä aikakauslehdessä
Thiourea Organocatalysts as Emerging Chiral Pollutants : En Route to Porphyrin-Based (Chir)Optical Sensing (2021)

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. Chemosensors, 9(10), Article 278. https://doi.org/10.3390/chemosensors9100278

JYU-tekijät tai -toimittajat

Truong, Khai-Nghi
Rissanen, Kari

Julkaisun tiedot

Julkaisun kaikki tekijät tai toimittajat: Konrad, Nele; Horetski, Matvey; Sihtmäe, Mariliis; Truong, Khai-Nghi; Osadchuk, Irina; Burankova, Tatsiana; Kielmann, Marc; Adamson, Jasper; Kahru, Anne; Rissanen, Kari; et al.

Lehti tai sarja: Chemosensors

eISSN: 2227-9040

Julkaisuvuosi: 2021

Ilmestymispäivä: 29.09.2021

Volyymi: 9

Lehden numero: 10

Artikkelinumero: 278

Kustantaja: MDPI AG

Julkaisumaa: Sveitsi

Julkaisun kieli: englanti

DOI: https://doi.org/10.3390/chemosensors9100278

Julkaisun avoin saatavuus: Avoimesti saatavilla

Julkaisukanavan avoin saatavuus: Kokonaan avoin julkaisukanava

Julkaisu on rinnakkaistallennettu (JYX): https://jyx.jyu.fi/handle/123456789/78613

Tiivistelmä

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.

YSO-asiasanat: orgaaniset yhdisteet; rikkiyhdisteet; katalyytit; ekotoksikologia; bakteerit; monitorointi; supramolekulaarinen kemia

Vapaat asiasanat: porphyrin; thiourea; chiral amine; organocatalyst; Takemoto’s catalyst; host–guest binding; chirality; supramolecular chemistry; circular dichroism; toxicity; chiral pollutants; Vibrio fischeri

Liittyvät organisaatiot

Hankkeet, joissa julkaisu on tehty

OKM-raportointi: Kyllä

Raportointivuosi: 2021

JUFO-taso: 1