A novel Schiff base: Synthesis, structural characterisation and comparative sensor studies for metal ion detections

Köse, Muhammet; Purtaş, Savaş; Güngör, Seyit Ali; Ceyhan, Gökhan; Akgün, Eyup; McKee, Vickie

doi:10.1016/j.saa.2014.10.025

Cited by 19 publications

(13 citation statements)

References 34 publications

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“…29 The 1 H NMR spectra of 3a and 3b showed characteristic sharp singlets at δ 10.01 and 9.73 ppm, respectively, confirming the presence of the azomethine ( CH N ) proton, and two singlets at δ 2.46-2.47 ppm (assigned to the CH 3 group attached to the carbon atom of the pyrazolone ring) and δ 3.16−3.20 ppm (assigned to the CH 3 group attached to the nitrogen atom of the pyrazolone ring). 18 Aromatic protons were also observed as expected δ 7.30-8.17 ppm as multiplets or doublets. In the EI-MS, 3a and 3b both exhibited a molecular ion peak [M] + at m/z 336 at intensities of 35% and 40%, respectively.…”

Section: Resultssupporting

confidence: 59%

“…The above results indicate that hetero atoms with high negative charges, i.e., O1, N1, and N3, could act as electron donors and coordinate with metals, which is consistent with the findings of previous studies. 17,18 Although, C11 was found to have relatively large negative value in 3a and 3b, it is probably not be involved in metal coordination for steric reasons. Molecular Surfaces.…”

Section: Resultsmentioning

confidence: 98%

“…The high-energy peaks observed at 286 and 284 nm could be due to π!π* transitions and the low energy peaks at 350 and 386 nm to n!π* transition in the Schiff-base moiety. 18 However, the π!π* transition of 3a showed red shift (2 nm) and hyperchromic shift vs. 3b, while the n!π* transition of 3b showed red shift (36 nm) and hyperchromic shift vs. 3a. The theoretical electronic absorption spectra were also predicted using the time-dependent density functional theory (TD-DFT) method based on the B3LYP/6-311G(d,p) level optimized structure of both the compounds, and compared with the corresponding experimental electronic spectrum (Table 4).…”

Section: Fluorescent Properties and Dft Analyses Of 4-aa Schiff Basesmentioning

confidence: 90%

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Novel Fluorescent Schiff Base Derivatives of 4‐Aminoantipyrine with Large Stokes Shifts and Dual Emission Properties: Crystal Structure, Molecular Interactions, Molecular Surfaces, Conformational and DFT Analyses

Alam

Lee

2015

Bulletin Korean Chem Soc

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Two novel Schiff base analogs derived from 4-aminoantipyrine, namely, (E)-4-(2-nitrobenzylideneamino)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one (3a) and (E)-4-(4-nitrobenzylideneamino)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one (3b), were synthesized using a mild and efficient method and characterized by FT-IR, 1 H NMR, mass spectrometry, and single-crystal X-ray diffraction studies. X-ray analysis of a single crystal of 3a revealed an orthorhombic space group P2 (1)2(1)2(1) structure, with an E-configuration around the azomethine ( C12 N3 ) double bond. One unit cell was found to contain four molecules showing π−π and π−σ van der Waals stacking interactions. Plausible intermolecular interactions were analyzed using 3D Hirshfeld surfaces and the related 2D fingerprint plots. The optimized molecular structure, potential energy surface (PES) scan, vibrational frequencies, Mulliken charge distribution, molecular electrostatic potential (MEP) maps, frontier molecular orbitals (FMOs), and associated energies of 3a and 3b were calculated using density functional theory (DFT) calculations using the B3LYP method and the 6-311G(d,p) basis set. PES scans showed that the conformational energy profiles of 3a and 3b were dissimilar around the torsion angles N3-C12-C13-C14/C18 and C12-N3-C3-C2/C1 due to substituent position effects on the benzylidene phenyl ring. Mulliken charge distribution analysis revealed that O1, N1, and N3 atoms of 3a and 3b could act as electron donors and coordinate with metals, while MEP analysis showed that O1, N3, and O2-O3 are the most suitable sites for electrophilic attack. Regarding drug-receptor interactions, molecular lipophilic potential (MLP) maps demonstrated that the benzylidene phenyl ring favors lipophilic contact and the pyrazolone ring hydrophilic contact. In addition, UV-vis and fluorescence spectroscopic experiments showed that both compounds have good absorbance and fluorescent properties and large Stokes shifts. Interestingly, both compounds showed dual emission in ethanol, acetone, and diethyl ether, possibly due to conformational isomerization induced by photoexcitation.

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Section: Resultssupporting

confidence: 59%

Section: Resultsmentioning

confidence: 98%

Section: Fluorescent Properties and Dft Analyses Of 4-aa Schiff Basesmentioning

confidence: 90%

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Novel Fluorescent Schiff Base Derivatives of 4‐Aminoantipyrine with Large Stokes Shifts and Dual Emission Properties: Crystal Structure, Molecular Interactions, Molecular Surfaces, Conformational and DFT Analyses

Alam

Lee

2015

Bulletin Korean Chem Soc

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“…The imine groups in Schiff bases are significant for biological activities, they are very useful active centers of many biological systems 10 . Schiff bases have played essential roles in understanding the coordination chemistry of transition metal ions.…”

Section: Abstract: Ni(ii) Mixed-ligand Complexes Of [Nilnh3]mentioning

confidence: 99%

Synthesis, spectroscopic, biological activities and DFT calculations of nickel(II) mixed-ligand complexes of tridentate Schiff bases

Demehin¹,

Oladipo

Semire

2020

Eclet. Quim. J.

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Ni(II) mixed-ligand complexes of [NiLNH3] (where L= N-salicylidene-o-aminophenol (L1), N-(5-methoxysalicylidene-o-aminophenol) (L2) and N-(2-hydroxy-1-naphthalidene)-o-aminophenol) (L3) containing ONO tridentate Schiff bases and ammonia were synthesized and characterized by elemental analysis, infrared, ultraviolet-visible, proton and carbon-13 spectroscopies. Theoretical calculations were also performed on the optimized structures of the Ni(II) mixed-ligand complexes. The Infrared and ultraviolet-visible spectra of the complexes were calculated, and the results compared with the corresponding experimental spectra to augment the experimental structural identification. The elemental analysis data confirmed the formation of 1:1:1 [metal: Schiff base: ammonia] molar ratio. The NMR spectra showed that the Schiff bases coordinated to the Ni(II) ion via the two deprotonated phenolic oxygen and azomethine nitrogen atoms. The biological studies showed that the complexes exhibited higher antibacterial and antioxidant activities than the free Schiff base ligands.

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“…Secondly, on the basis of good binding-selectivity, the fluorescence signal should avoid environmental interference (signal-selectivity) [9]. In this respect Schiff base ligands are very attracting to be used as sensing material for chemosensor because they are easy to coordinate with metal ions [10].…”

mentioning

confidence: 99%

Fluorescent Chemosensor Bearing Amine and Benzenyl Functionality for Fe3+ Ions Detection in Aqueous Solution

Hasan¹,

Zakaria²,

Adnan³

2017

IJCEA

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A novel Schiff base: Synthesis, structural characterisation and comparative sensor studies for metal ion detections

Cited by 19 publications

References 34 publications

Novel Fluorescent Schiff Base Derivatives of 4‐Aminoantipyrine with Large Stokes Shifts and Dual Emission Properties: Crystal Structure, Molecular Interactions, Molecular Surfaces, Conformational and DFT Analyses

Novel Fluorescent Schiff Base Derivatives of 4‐Aminoantipyrine with Large Stokes Shifts and Dual Emission Properties: Crystal Structure, Molecular Interactions, Molecular Surfaces, Conformational and DFT Analyses

Synthesis, spectroscopic, biological activities and DFT calculations of nickel(II) mixed-ligand complexes of tridentate Schiff bases

Fluorescent Chemosensor Bearing Amine and Benzenyl Functionality for Fe3+ Ions Detection in Aqueous Solution

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