Synthesis of a novel hydrazone-based compound applied as a fluorescence turn-on chemosensor for iron(<scp>iii</scp>) and a colorimetric sensor for copper(<scp>ii</scp>) with antimicrobial, DFT and molecular docking studies

Patwary, Md Abdul Majed; Ghann, William; Adamu, Abdullahi; Uddin, A. K. M. Royhan; Mahmud, Md. Mayez; Haque, Md. Aminul; Uddin, Jamal; Kazi, Mohsin

doi:10.1039/d3ra04364a

Cited by 5 publications

(2 citation statements)

References 41 publications

(60 reference statements)

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“…Iron is the fourth most prevalent element in the environment after aluminum. 5–8 Iron is vital for living organisms, including humans, as it has direct involvement in numerous cellular processes. 9 However, ensuring appropriate levels of iron is of utmost importance, since excess iron has been associated with a variety of illnesses such as cancer, hepatitis, hemochromatosis, and organ failure.…”

Section: Introductionmentioning

confidence: 99%

Morphological adaptability through structural alterations in an AIE active novel chemosensor with Al(iii), Fe(iii), and gas phase/aqueous phase TNP recognition ability

Das,

Biswas

et al. 2024

New J. Chem.

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Section: Introductionmentioning

confidence: 99%

Morphological adaptability through structural alterations in an AIE active novel chemosensor with Al(iii), Fe(iii), and gas phase/aqueous phase TNP recognition ability

Das,

Biswas

et al. 2024

New J. Chem.

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“…Schiff base hydrazones have a variety of applications in analytical chemistry, including the selective extraction of certain transition metals and their use in spectroscopic determination [11,12]. Additionally, hydrazones are versatile compounds that can be used in the construction of sensor materials for detecting fluoride ions, cyanide ions, heavy metals, and poisonous fumes [13][14][15][16][17].…”

Section: Introductionmentioning

confidence: 99%

1-(2,4-Dinitrophenyl)-2-((Z)-2-((E)-4-fluorobenzylidene)-3,4-dihydronaphthalen-1(2H)-ylidene)hydrazine

Abdel-Wahab,

Mohamed,

Kariuki

et al. 2024

Molbank

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The reaction of (E)-2-(4-fluorobenzylidene)-3,4-dihydronaphthalen-1(2H)-one and (2,4-dinitrophenyl)hydrazine in boiling ethanol containing hydrochloric acid (0.2 mL; 37%) for 1.5 h gave 1-(2,4-dinitrophenyl)-2-(2-(4-fluorobenzylidene)-3,4-dihydronaphthalen-1(2H)-ylidene)hydrazine in a 90% yield. Various spectral analyses, including NMR, and X-ray crystallography established the structure of the newly synthesized hydrazone.

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Heterocyclic fluorescent Schiff base chemosensors for the detection of Fe(III) and Cu(II) ions

Sambamoorthy,

Thamaraichelvan,

Karikalan

et al. 2024

Luminescence

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Two new Schiff bases were synthesized from 1‐(2,4‐dihydroxyphenyl)ethanone and pyridine derivatives. Both compounds were characterized using infrared, UV–Vis., 1H NMR, 13C NMR and mass spectral studies. Density functional theory (DFT) calculations were performed for both the Schiff bases with 6‐31G(d, p) as the basis set. Vibrational frequencies calculated using the theoretical method were in good agreement with the experimental values. Both the Schiff bases were highly fluorescent in nature. The cation‐recognizing profile of the compounds was investigated in aqueous methanol medium. The Schiff base 4‐(1‐(pyridin‐4‐ylimino)ethyl)benzene‐1,3‐diol (PYEB) was found to interact with Fe(III) and Cu(II) ions, whereas the Schiff base 4,4′‐((pyridine‐2,3‐diylbis(azanylylidene))bis(ethan‐1‐yl‐1‐ylidene))bis(benzene‐1,3‐diol) (PDEB) was found to detect Cu(II) ions. The mechanism of recognition was established as combined excited state intramolecular proton transfer (ESIPT)–chelation‐enhanced fluorescence (CHEF) effect and chelation‐enhanced quenching (CHEQ) process for the detection of Fe(III) and Cu(II) ions, respectively. The stability constant of the metal complexes formed during the sensing process was determined. The limit of detection for Fe(III) and Cu(II) ions with respect to Schiff base PYEB was found to be 1.64 × 10−6 and 2.16 × 10−7 M, respectively. With respect to Schiff base PDEB, the limit of detection for Cu(II) ion was found to be 4.54 × 10−4 M. The Cu(II) ion sensing property of the Schiff base PDEB was applied in bioimaging studies for the detection of HeLa cells.

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Synthesis of a novel hydrazone-based compound applied as a fluorescence turn-on chemosensor for iron(iii) and a colorimetric sensor for copper(ii) with antimicrobial, DFT and molecular docking studies

Abstract: A novel molecule 5-bromo-2-hydroxy-N′-[(1E)-1-(thiophen-2-yl)ethylidene]benzohydrazide (L) has been designed and synthesized. The sensing studies of L showed a ratio metric & turn-on-enhanced fluorescence and colorimetric response toward Fe3+ and Cu2+ ions respectively.

Cited by 5 publications

References 41 publications

Morphological adaptability through structural alterations in an AIE active novel chemosensor with Al(iii), Fe(iii), and gas phase/aqueous phase TNP recognition ability

Morphological adaptability through structural alterations in an AIE active novel chemosensor with Al(iii), Fe(iii), and gas phase/aqueous phase TNP recognition ability

1-(2,4-Dinitrophenyl)-2-((Z)-2-((E)-4-fluorobenzylidene)-3,4-dihydronaphthalen-1(2H)-ylidene)hydrazine

Heterocyclic fluorescent Schiff base chemosensors for the detection of Fe(III) and Cu(II) ions

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