Dataset Information

A Highly Selective and Sensitive Sequential Recognition Probe Zn²⁺ and H₂PO₄^- Based on Chiral Thiourea Schiff Base.

ABSTRACT: A series of novel chiral thiourea fluorescent probes HL₁-HL₆ were designed and synthesized from (1R,2R)-1,2-diphenylethylenediamine, phenyl isothiocyanate, and different substituted salicylic aldehydes. All of the compounds were confirmed by ¹H NMR, ¹³C NMR, and HRMS. They exhibit high selectivity and sensitivity to Zn²⁺ in the presence of nitrate ions with the detection limit of 2.3 × 10^-8 M (HL₅). Meanwhile, their zinc (II) complexes (L-ZnNO₃) showed continuous response to H₂PO₄^- 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 HL₁-HL₆ based on chiral thiourea Schiff base will be promising detection devices for Zn²⁺ and H₂PO₄^-.

SUBMITTER: Yang S

PROVIDER: S-EPMC10221379 | biostudies-literature | 2023 May

REPOSITORIES: biostudies-literature

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Publications

A Highly Selective and Sensitive Sequential Recognition Probe Zn2+ and H2PO4- Based on Chiral Thiourea Schiff Base.

Yang Shan S Huang Yichuan Y Lu Aidang A Wang Ziwen Z Li Hongyan H

Molecules (Basel, Switzerland) 20230518 10

A series of novel chiral thiourea fluorescent probes HL1-HL6 were designed and synthesized from (1R,2R)-1,2-diphenylethylenediamine, phenyl isothiocyanate, and different substituted salicylic aldehydes. All of the compounds were confirmed by 1H NMR, 13C NMR, and HRMS. They exhibit high selectivity and sensitivity to Zn2+ in the presence of nitrate ions with the detection limit of 2.3 × 10-8 M (HL<sub ...[more]

PMID: 37241910

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Project description:Condensation of 2-hydroxybenzaldehyde (salicylaldehyde) or 2-hydroxy-1-naphthaldehyde with 2-ethylaniline yields the Schiff base compound of (E)-2-(((2-ethylphenyl)imino)methyl)phenol (HL1) or (E)-1-(((2-ethylphenyl)imino)methyl)naphthalen-2-ol (HL2), which in turn react with the dinuclear complex of [Rh(η4-cod)(µ-O2CCH3)]2 (cod = cycloocta-1,5-diene) to afford the mononuclear (η4-cod){(E)-2-(((2-ethylphenyl)imino)methyl)phenolato-κ2N,O}rhodium(I), [Rh(η4-cod)(L1)] (1) or (η4-cod){(E)-1-(((2-ethylphenyl)imino)methyl)naphthalen-2-olato-κ2N,O}rhodium(I), [Rh(η4-cod)(L2)] (2) (L1 or L2 = deprotonated Schiff base ligand). The X-ray structure determination revealed that the HL2 exists in the solid state not as the usual (imine)N···H-O(phenol) form (enolamine form) but as the zwitterionic (imine)N-H+···-O(phenol) form (ketoamine form). 1H NMR spectra for HL2 in different solvents demonstrated the existence of keto-enol tautomerism (i.e., keto ⇆ enol equilibrium) in solution. The structure for 1 and 2 showed that the deprotonated Schiff base ligand coordinates to the Rh(η4-cod)-fragment as a six-membered N^O-chelate around the rhodium atom with a close-to-square-planar geometry. Two symmetry-independent molecules (with Rh1 and Rh2) were found in the asymmetric unit in 1 in a structure with Z' = 2. The supramolecular packing in HL2 was organized by π-π and C-H···π contacts, while only two recognized C-H···π contacts were revealed in 1 and 2. Remarkably, there were reciprocal or pairwise C-H···π contacts between a pair of each of the symmetry-independent molecules in 1. This pairwise C-H contact to the Rh-N^O chelate (metalloaromatic) ring may be a reason for the two symmetry-independent molecules in 1. Differential scanning calorimetry (DSC) analyses revealed an irreversible phase transformation from the crystalline-solid to the isotropic-liquid phase and subsequently confirmed the thermal stability of the compounds. Absorption spectra in solution were explained by excited state properties from DFT/TD-DFT calculations.

Dataset Information

A Highly Selective and Sensitive Sequential Recognition Probe Zn²⁺ and H₂PO₄^- Based on Chiral Thiourea Schiff Base.

Publications

A Highly Selective and Sensitive Sequential Recognition Probe Zn<sup>2+</sup> and H<sub>2</sub>PO<sub>4</sub><sup>-</sup> Based on Chiral Thiourea Schiff Base.

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