Synthesis, characterization and antimicrobial studies of 2-{(E)-[(2-hydroxy-5-methylphenyl)imino]methyl}-4-[(E)-phenyldiazenyl]phenol as a novel azo-azomethine dye

Köse, Muhammet; Kurtoğlu, Nurcan; Gümüşsu, Özkan; Tutak, Mustafa; McKee, Vickie; Karakaş, Duran; Kurtoğlu, Mükerrem

doi:10.1016/j.molstruc.2013.09.013

Cited by 45 publications

(19 citation statements)

References 31 publications

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“…The azo-aldehyde compound 2-hydroxy-5-[(E)-phenyldiazenyl] benzaldehyde (a) was prepared according to the published papers [40,41]. The azo-azomethine ligand (HL) was prepared according to the known condensation method.…”

Section: Synthesis Of 2-hydroxy-5-[(e)-phenyldiazenyl]benzaldehyde (A)mentioning

confidence: 99%

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An azo-azomethine ligand and its copper(II) complex: Synthesis, X-ray crystal structure, spectral, thermal, electrochemical and photoluminescence properties

Eren

Köse

Kurtoğlu

et al. 2015

Inorganica Chimica Acta

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Section: Synthesis Of 2-hydroxy-5-[(e)-phenyldiazenyl]benzaldehyde (A)mentioning

confidence: 99%

“…Recently, some azo-azomethines and their metal chelates have been reported [36][37][38][39]. In our previous work, 4-[(E)-phenyldiazenyl]-2-[(E)-(phenylimino)methyl]phenol and 2-{(E)-[(2-hydroxy-5-methylphenyl)imino]methyl}-4-[(E)-phenyldiazenyl]phenol compounds were synthesized and structurally characterized [40,41].…”

Section: Introductionmentioning

confidence: 99%

An azo-azomethine ligand and its copper(II) complex: Synthesis, X-ray crystal structure, spectral, thermal, electrochemical and photoluminescence properties

Eren

Köse

Kurtoğlu

et al. 2015

Inorganica Chimica Acta

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“…Recently, extensive attention has been paid to the study of azo Schiff base compounds containing hydroxyl groups. The tautomerism in polyhydroxy derivatives of azo‐azomethine dyes play a valuable role in chemistry and biochemistry . The presence of different tautomer forms in these compounds can strongly impact on their photo‐chemical properties.…”

Section: Introductionmentioning

confidence: 99%

New Chloro‐Based Azo‐Azomethine Dyes: Synthesis, Biological and Optical Spectroscopic Studies for Detection of some Transition Metal Ions

Shaghaghi

Rezanezhad

2018

ChemistrySelect

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Two new chromogenic receptors 1,2-[1-(3-imino-4-hydroxophenylazobenzene)]-4-chlorobenzene (1 a) and 1,2-[1-(3-imino-4hydroxophenylazo-4-nitrobenzene)]-4-chlorobenzene (1 b) have been designed and chearcterized for detection of some transition metal ions in DMSO solution by UV/Vis spectroscopy. Upon addition of Cd 2 + , Zn 2 + and Cu 2 + ions to 1 a in DMSO, the peak at 460 nm increases in intensity, while the band at 352 nm decreases in intensity and approximately disappears. n!p* transition of azo groups of 1 a decreases in intensity after adding Hg 2 + ions and does not change after adding Ni 2 + ions. This indicates high tendency of 1 a towards Cd 2 + , Zn 2 + and Cu 2 + against Ni 2 + and Hg 2 + ions. Compound 1 b shows some color changes after addition of metal ions. Upon addition of all metal ions to 1 b in DMSO, the band at 560 nm increases in intensity with the hypsochromic shift for Cu 2 + , Zn 2 + , Co 2 + and Ni 2 + . But the largest blue shift (-67 nm) is seen after adding Cu 2 + ion with remarkable color change from violet-green to orange. Benesi-Hildebrand plot and Job's method are used for determination of binding constant (K a ) and stoichiometry of formed complexes with 1 b. Then, complex Cu(II) with 1 b is synthezied for recognition of binding sites of ligand. The results indicate that 1 b behaves as one tetradentate ligand with N and O donor atoms when bound to Cu(II). Moreover, the study of antioxidant properties of 1 a and 1 b with DPPH method reveals good and significant activity.[a] Dr.

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“…and HL4, excess amounts) and NH 2 OH.HCI (0.68 g for HL1, 0.56 for HL2, 0.59 g for HL3 and HL4, excess amounts) were added to the solutions 21,22 and refluxed for 2 h. The reaction mixture was then poured into ice-cooled water (250 mL) and precipitates were collected by filtration and dried in air.…”

Section: Synthesis Of Azo-oxime Compounds Hl1ox-hl4oxmentioning

confidence: 99%

New diazo-containing phenolic oximes: structural characterization, computationalstudies, and solvent extraction of Cu(II), Ni(II), and Zn(II) ions

Karabörk¹,

Kırpık²,

Sayın³

et al. 2019

Turk J Chem

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In the current study, four new phenolic oxime ligands (HL1ox-HL4ox) containing diazo groups (-N = N-) were synthesized and used for liquid-liquid extraction of heavy metal ions [Cu(II), Ni(II), and Zn(II)]. The new compounds were characterized by analytical and spectroscopic methods. Solid-state structures of HL1ox-HL3ox were determined by single-crystal X-ray diffraction studies. Hirshfeld surface analysis of the compounds was performed to determine the contribution of different intermolecular contacts to the stability of the structures. The HL1ox-HL4ox ligands showed higher extraction performance for Cu(II) ion than Ni(II) and Zn(II) ions. The effect of pH on extraction capacity was investigated and the oxime compounds showed high extraction capacity at low pH values. The effects of the substitute groups (at the meta position of the phenol ring) on the extraction were investigated. Within the oxime ligands, the HL3ox compound exhibited higher extraction capacity for Cu(II) ions. The better extraction value of HL3ox is attributed to the weak hydrogen bond type interactions, which result in more stable complexes.

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Synthesis, characterization and antimicrobial studies of 2-{(E)-[(2-hydroxy-5-methylphenyl)imino]methyl}-4-[(E)-phenyldiazenyl]phenol as a novel azo-azomethine dye

Cited by 45 publications

References 31 publications

An azo-azomethine ligand and its copper(II) complex: Synthesis, X-ray crystal structure, spectral, thermal, electrochemical and photoluminescence properties

An azo-azomethine ligand and its copper(II) complex: Synthesis, X-ray crystal structure, spectral, thermal, electrochemical and photoluminescence properties

New Chloro‐Based Azo‐Azomethine Dyes: Synthesis, Biological and Optical Spectroscopic Studies for Detection of some Transition Metal Ions

New diazo-containing phenolic oximes: structural characterization, computationalstudies, and solvent extraction of Cu(II), Ni(II), and Zn(II) ions

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