Effect of O-substitution in imidazole based Zn(<scp>ii</scp>) dual fluorescent probes in the light of arsenate detection in potable water: a combined experimental and theoretical approach

Biswas, Sneha; Chowdhury, Tania; Ghosh, Avik; Das, Abhijit K.; Das, Debasis

doi:10.1039/d2dt00357k

Cited by 11 publications

(14 citation statements)

References 64 publications

(64 reference statements)

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“…1 H [ppm]: 2.30 (s, 6H) (H1), CH 3 , 4.40 (s, 4H) (H6), CH 2 , 6.31 (s, 2H) Ar-H (3), 6.75–6.78 (td, 2H, J = 1.16 Hz, J = 7.5 Hz) Ar-H (9), 6.92–6.94 (dd, 2H, J = 8.2 Hz, 1 Hz) Ar-H (10), 7.01–7.03 (dd, 2H, J = 8 Hz, 1.5 Hz) Ar-H (8), 7.13–7.14 (d, 2H, J = 1,5 Hz) Ar-H (15), 7.17–7.18 (d, 2H, J = 1.9 Hz) Ar-H (11), 8.55 (s, 2H) -N=CH-, 13.5 (s, 2H) -OH, ( Figure S1 ) 13 C [ppm]: 20.36 (C1), 46.91 (C6), 111.78 (C8), 117.44 (C14), 117.99 (C9), 119.55 (C10), 125.33 (C4), 128.18 (C11), 128.30 (C3), 131.57 (C15), 134.28 (C7), 136.11 (C12) 143.49 (C2) 157.36 (C5) 161.76 (C13) [ 33 , 34 ] ( Figure S2 ). Selected FT-IR (data reflectance, crystal) (cm −1 ) 3405 ν OH , 3070, 2634 ν C-HAr , 1600, 1587 ν C=N , 1508 ν C=CHA , 1467, 1367 ν C=CAr , 1323 ν C-NHA , 1288 ν Ph-O .…”

Section: Methodsmentioning

confidence: 99%

“…1 H [ppm]: 1.35 (s, 18H) (H1), CH 3 , 4.48 (s, 4H) (H7), CH 2 , 6.81–6.82 (t, 2H, J = 7.2 Hz) Ar-H (4), 7.00–7.01 (d, 2H, J = 7.7 Hz) Ar-H (11), 7.08–7.09 (dd, 2H, J = 7.6 Hz, 1.3 Hz)) Ar-H (10), 7.27–7.28 (dd, 2H, J = 15.5 Hz, 1.6 Hz) Ar-H (9), 7.37 (d, 2H, J = 2.4 Hz) Ar-H (12), 7.45 (d, 2H, J = 2.4 Hz) Ar-H (16), 8.65 (s, 2H) -N=CH-, 13.57 (s, 2H) -OH, ( Figure S3 ) 13 C [ppm]: 31.42 (C1), 34.05 (C2), 47.37 (C7), 111.90 (C9), 117.56 (C15), 117.98 (C10), 119.21 (C11), 124.99 (C16), 128.05 (C4, C6, C5), 128.24 (C12), 130.88 (C8), 136.24 (C13), 141.89 (C3), 157.26 (C6), 162.15 (C14) ( Figure S4 ) [ 33 , 34 ].…”

Section: Methodsmentioning

confidence: 99%

“…It has been intimately researched that Schiff base ligands are also organic sensors with selectivity for the different metal ions; they detect both anions and cations [ 31 , 32 , 33 , 34 ]. Two zinc(II) complexes obtained from differently O-substituted imidazole based homologous Schiff bases: 2-((E)-(3-(1H-imidazole-1-yl)propylimino)methyl)-6-ethoxyphenol) and 2-((E)-(3-(1H-imidazole-1-yl)propylimino)methyl)-6-methoxyphenol) were synthesized.…”

Section: Introductionmentioning

confidence: 99%

“…Two zinc(II) complexes obtained from differently O-substituted imidazole based homologous Schiff bases: 2-((E)-(3-(1H-imidazole-1-yl)propylimino)methyl)-6-ethoxyphenol) and 2-((E)-(3-(1H-imidazole-1-yl)propylimino)methyl)-6-methoxyphenol) were synthesized. Their sensitivity and selectivity toward arsenate were checked [ 33 ]. Interestingly, despite the small structural differences, the various sensitive fluorescence behavior toward arsenic was noted.…”

Section: Introductionmentioning

confidence: 99%

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Experimental and Theoretical Studies of the Optical Properties of the Schiff Bases and Their Materials Obtained from o-Phenylenediamine

et al. 2022

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Two macrocyclic Schiff bases derived from o-phenylenediamine and 2-hydroxy-5-methylisophthalaldehyde L1 or 2-hydroxy-5-tert-butyl-1,3-benzenedicarboxaldehyde L2, respectively, were obtained and characterized by X-ray crystallography and spectroscopy (UV-vis, fluorescence and IR). X-ray crystal structure determination and DFT calculations for compounds confirmed their geometry in solution and in the solid phase. Moreover, intermolecular interactions in the crystal structure of L1 and L2 were analyzed using 3D Hirshfeld surfaces and the related 2D fingerprint plots. The 3D Hirschfeld analyses show that the most numerous interactions were found between hydrogen atoms. A considerable number of such interactions are justified by the presence of bulk tert-butyl groups in L2. The luminescence of L1 and L2 in various solvents and in the solid state was studied. In general, the quantum efficiency between 0.14 and 0.70 was noted. The increase in the quantum efficiency with the solvent polarity in the case of L1 was observed (λex = 350 nm). For L2, this trend is similar, except for the chloroform. In the solid state, emission was registered at 552 nm and 561 nm (λex = 350 nm) for L1 and L2, respectively. Thin layers of the studied compounds were deposited on Si(111) by the spin coating method or by thermal vapor deposition and studied by scanning electron microscopy (SEM/EDS), atomic force microscopy (AFM), spectroscopic ellipsometry and fluorescence spectroscopy. The ellipsometric analysis of thin materials obtained by thermal vapor deposition showed that the band-gap energy was 3.45 ± 0.02 eV (359 ± 2 nm) and 3.29 ± 0.02 eV (377 ± 2 nm) for L1/Si and L2/Si samples, respectively. Furthermore, the materials of the L1/Si and L2/Si exhibited broad emission. This feature can allow for using these compounds in LED diodes.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Experimental and Theoretical Studies of the Optical Properties of the Schiff Bases and Their Materials Obtained from o-Phenylenediamine

et al. 2022

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“…To ensure real-life applicability of arsenate detection in water samples, our synthesized spinel nanomaterial ZAZ has been put to use to coat a paper strip − made up of Whatman-40 filter paper. After coating, the strip appears colorless in ambient light and bright cyan under a UV lamp.…”

Section: Resultsmentioning

confidence: 99%

ZnAl₂O₄ Nanomaterial as a Naked-Eye Arsenate Sensor: A Combined Experimental and Computational Mechanistic Approach

Chowdhury

Chakraborty

Ghosh

et al. 2022

ACS Appl. Mater. Interfaces

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Raising public awareness over the emerging health risk due to intake of arsenic-contaminated potable water is a matter of great concern. Exploration of cost-effective, self-testing kits is a substantial way to reach out to the masses and detect the presence of arsenate in water. With this agenda, a photoluminescent Mannich base Zn(II) complex (ZnMC = [Zn2(ML)2]·(ClO4)2·(H2O); HML = Mannich base ligand) has been synthesized, and its dinuclearity was verified with single-crystal X-ray diffraction structural analysis. Among a range of anions, ZnMC was found to detect arsenate selectively by showing a turn-off emission with a color change from bright green to dark under UV light. The real-life applicability of the ZnMC probe is somewhat restricted to only sensing of arsenate, but not its removal owing to the fact of its homogeneity. Considering the efficacy of ZnMC as well as a need for its easy removal from water, slight modification has been done with chloride ions in the form of ZnMC″ (=[Zn2(ML)2(Cl)2]), and finally, an interface between homogeneous and heterogeneous solid support has been explored with a strategic fabrication of ZnMC″ grafted ZnAl2O4, named as ZAZ nanomaterial. This not only imparts successful segregation of arsenate from drinking water but also provides naked-eye detection under ambient light as well as UV light. Thermodynamic parameters associated with the binding of arsenate to ZnMC and ZAZ have been evaluated through isothermal calorimetric (ITC) measurements. Steady-state and time-resolved fluorescence titration study, absorption titration study, scanning electron microscopy (SEM), transmission electron microscopy (TEM), and computational calculations have been performed to get deep insights into the sensing properties. Proper justification of the sensing mechanism is the highlight of this work. ZAZ nanomaterial has been exploited to produce a self-test paper kit for arsenate detection with a limit of 9.86 ppb, which potentially enables applications in environmental monitoring.

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Improving the Efficiency of Luminescent Zn(II)‐Modified N‐Doped GOQD Nanomaterials in Parkinson's Disease Treatment: A Theoretical Mechanistic Framework Exploring Doping Effect

Biswas,

Chowdhury,

Banerjee

et al. 2024

Chemistry An Asian Journal

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Levodopa, a widely prescribed drug in Parkinson's disease treatment, stands as the foremost prodrug of dopamine. An affordable self‐testing kit is utilized to monitor levodopa content in anti‐parkinson drugs in human serum. A photoluminescent trinuclear Zn(II) complex [Zn3(L)2(κ1‐OAc)2(κ2‐OAc)2] has been synthesized, which cleaves into mononuclear ZC in aqueous solution. ZC was found to detect L‐Dopa in Tris‐HCl buffer, exhibiting a moderate decrease in PL‐emission. The real‐life utility of the ZC probe is limited, for its lower sensitivity (LOD 35.3 µM) and separation challenges. Therefore, an interface between homogeneous and heterogeneous supports has been explored, leading to the strategic development of NGOZC, where ZC was grafted onto NGOQD. This material enables naked‐ eye detection under both ambient and UV light with color change from bright cyan to green, followed by dark. The nitrogen doping effect was investigated by several comparative investigations involving the synthesis of ZC‐grafted GOQD, leading to enhanced quenching performance. Steady‐state and time‐resolved fluorescence titration study, morphological analysis, and computational calculations have been performed to get insights into the sensing mechanism. To the best of our knowledge, this as‐synthesized NGOZC (LOD 1.78 nM) represents a promising strategy and platform for applications in biosensors, especially for Parkinson's and Alzheimer's diseases.

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Effect of O-substitution in imidazole based Zn(ii) dual fluorescent probes in the light of arsenate detection in potable water: a combined experimental and theoretical approach

Abstract: Efficient detection of arsenate (AsO43-) from contaminated drinking water extracted from underground becomes a matter of utmost necessity as well as exquisite challenge owing to on growing public health damage...

Cited by 11 publications

References 64 publications

Experimental and Theoretical Studies of the Optical Properties of the Schiff Bases and Their Materials Obtained from o-Phenylenediamine

Experimental and Theoretical Studies of the Optical Properties of the Schiff Bases and Their Materials Obtained from o-Phenylenediamine

ZnAl₂O₄ Nanomaterial as a Naked-Eye Arsenate Sensor: A Combined Experimental and Computational Mechanistic Approach

Improving the Efficiency of Luminescent Zn(II)‐Modified N‐Doped GOQD Nanomaterials in Parkinson's Disease Treatment: A Theoretical Mechanistic Framework Exploring Doping Effect

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Effect of O-substitution in imidazole based Zn(ii) dual fluorescent probes in the light of arsenate detection in potable water: a combined experimental and theoretical approach

Abstract: Efficient detection of arsenate (AsO43-) from contaminated drinking water extracted from underground becomes a matter of utmost necessity as well as exquisite challenge owing to on growing public health damage...

Cited by 11 publications

References 64 publications

Experimental and Theoretical Studies of the Optical Properties of the Schiff Bases and Their Materials Obtained from o-Phenylenediamine

Experimental and Theoretical Studies of the Optical Properties of the Schiff Bases and Their Materials Obtained from o-Phenylenediamine

ZnAl2O4 Nanomaterial as a Naked-Eye Arsenate Sensor: A Combined Experimental and Computational Mechanistic Approach

Improving the Efficiency of Luminescent Zn(II)‐Modified N‐Doped GOQD Nanomaterials in Parkinson's Disease Treatment: A Theoretical Mechanistic Framework Exploring Doping Effect

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Product

Resources

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ZnAl₂O₄ Nanomaterial as a Naked-Eye Arsenate Sensor: A Combined Experimental and Computational Mechanistic Approach