A series of novel chiral thiourea fluorescent probes - were designed and synthesized from (1,2)-1,2-diphenylethylenediamine, phenyl isothiocyanate, and different substituted salicylic aldehydes. All of the compounds were confirmed by H NMR, C NMR, and HRMS. They exhibit high selectivity and sensitivity to Zn in the presence of nitrate ions with the detection limit of 2.3 × 10 M (). Meanwhile, their zinc (II) complexes (-ZnNO) showed continuous response to HPO in acetonitrile solution. The identification processes could further be verified by supramolecular chemistry data analysis, X-ray single-crystal diffraction analysis, and theoretical study. The research provides reliable evidence for an explanation of the mechanism of action of thiourea involved in coordination, which is important for the application of thiourea fluorescent probes. In short, the sensors - based on chiral thiourea Schiff base will be promising detection devices for Zn and HPO.
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http://dx.doi.org/10.3390/molecules28104166 | DOI Listing |
Molecules
November 2024
Departamento de Química Orgánica e Inorgánica, Facultad de Ciencias, and Instituto del Agua, Cambio Climático y Sostenibilidad (IACYS)-Unidad de Química Verde y Desarrollo Sostenible, Universidad de Extremadura, 06006 Badajoz, Spain.
This publication reports a facile and convenient preparation of tri--acetyl-glucopyranoses, derived from the corresponding 2-deoxyaminosugar, where the vicinal anomeric and C2 positions are decorated by azido and (thio)ureido groups, respectively. This double functionalization leads to an inherently chiral core incorporating the versatile azido and (thio)ureido linkages prone to further manipulation. The latter also provides a structural element for hydrogen-bonded donor-acceptor (HB-DA) sites, which are of immense value in organocatalytic pursuits.
View Article and Find Full Text PDFBiopolymers
January 2025
Department of Chemistry, Faculty of Engineering and Science, Bursa Technical University, Bursa, Turkey.
Cellulose is one of the most abundant biopolymers in nature. Despite being the subject of research in various fields, it is not as famous as chitosan in catalyst design. Herein, a novel thiourea-functionalized cellulose (CTU-6) was synthesized as a robust hydrogen bonding catalyst with the degree of substitution (DS) of 0.
View Article and Find Full Text PDFOrg Lett
December 2024
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, State Key Laboratory of Petroleum Molecular & Process Engineering, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200050, China.
We report herein the enantioselective photoinduced Nazarov reaction using a relay strategy of an electrocyclization, followed by parallel kinetic resolution (PKR). No enantioselectivity was observed during electrocyclization due to weak coordination between chiral ligands and the substrate's carbonyl group. However, PKR was successfully achieved in the deprotonation step with a bifunctional chiral thiourea ligand.
View Article and Find Full Text PDFAcc Chem Res
November 2024
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China.
J Org Chem
October 2024
Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur, Uttar Pradesh 208016, India.
Chiral bifunctional thiourea-catalyzed Diels-Alder reaction between olefinic azlactones and alkylidene thiazolone derivatives is reported here for the first time. The asymmetric Diels-Alder reaction delivers vicinal tertiary-quaternary stereocenters in spirocyclohexenone thiazolones in moderate to high yields and good stereochemical outcomes. The protocol can be adapted to a broad array of substrates.
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