Synthesis of some transition metal complexes with new heterocyclic thiazolyl azo dye and their uses as sensitizers in photo reactions

Al-Adilee, Khalid J.; Abass, Ahmed K.; Taher, Ali M.

doi:10.1016/j.molstruc.2015.11.038

Cited by 57 publications

(27 citation statements)

References 40 publications

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“…The multiple signals at 2.6 ppm belong to the methyl group attached at the azometine group, the signal appearing at 1.2 ppm belongs to the methyl group of the solvent [26,27]. The singalet signal showed at (11.5) ppm attributed to (N-H) of phenyl hydrazine.…”

Section: H Nmr Of Free Ligand (Dpdpih)mentioning

confidence: 99%

Synthesis and Characterization of New Azo 4,5-dimethyl-2-((3-((E)-1-(2-phenylhydrazono)ethyl)phenyl)diazenyl)-1H-imidazole and its Metal(II) Complexes

Mahmoud¹,

Musa²,

Obaid³

2018

Asian J. Chem.

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INTRODUCTIONThe heterogeneous azo ligands are newly bonded, compared to their previous ligands of ring homogeneous. The importance of its features is the inclusion of one of its rings association with the azo group or both [1,2] on one atom and at least in its annular structure, which can be in coordination with the metal ions.The heterogeneous ligands of the nitrogen containing nitrogen ring are more common than other ligands containing oxygen atoms in their chemical composition [3]. The imidazole belongs to a class of compound called the azolates, which were prepared by Debus [4]. The imidazole is similar to pyrimidine in its chemical composition, both of which contain heterogeneous nitrogen atoms in their heterogeneous ring [5]. The nitrogen atom of the azole has free pair of electron and does not share to fixation of imidazole, caused the basicity of this ring and is easy to bond with the metal ions [6].The imidazole molecule is a stronger base than pyridine and it possesses the two resonance formulas. The electron density calculations showed that the electrophilic attack must occur at the two positions of this molecule. The azo ligands derived from this molecule or its derivatives have proved this fact [7]. EXPERIMENTALAll the chemicals used in this work were of highest purity available and were purchased from commercial sources (BDH 3-((E)-1-(2-phenylhydrazono) In this paper, a new azo ligand, 4,5-dimethyl-2-((3-((E)-1-(2-phenylhydrazono)ethyl)phenyl)diazenyl)-1H-imidazole (DPDPIH) and its metal complexes were synthesized. The ligand (DPDPIH) and its metal complexes were characterized by elemental, IR, 1 H NMR electronic and mass spectra. The values of elemental microanalysis and metal contents were in good agreement with the calculated values. The molar conductivity indicated that all these metal complexes were non-electrolyte in nature. The magnetic susceptibility values indicated that all the metal complexes were paramagnetic except cadmium and zinc complexes. Synthesis and Characterization of New Azo 4,5-dimethyl-2-((

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Section: H Nmr Of Free Ligand (Dpdpih)mentioning

confidence: 99%

Synthesis and Characterization of New Azo 4,5-dimethyl-2-((3-((E)-1-(2-phenylhydrazono)ethyl)phenyl)diazenyl)-1H-imidazole and its Metal(II) Complexes

Mahmoud¹,

Musa²,

Obaid³

2018

Asian J. Chem.

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“…Thus, IR spectrum of 3indicated absorption bands at v max = 3370 cm −1 for hydroxyl group, 1653 cm −1 for carbonyl group and 1456, 1290 cm −1 for nitro group. 1 H NMR spectrum showed three singlet signals at δ = 8.05, 10.30 and 11.78 ppm corresponding to H 6 of hyroxyphenyl ring, hydroxyl and formyl protons, respectively, two doublet signals, each doublet for two protons at δ = 7.95 and 8.32 ppm for H 2,6 and H 3,5 of nitrophenyl ring, respectively, two doublet signals, each doublet for one proton at δ = 7.17 and 8.14 ppm due to H 3 and H 4 of hyroxyphenyl ring, respectively. IR spectrum of compound 4 showed absorption bands at v max = 3462 cm −1 for hydroxyl group, v max = 1658 cm −1 for carbonyl group and v max = 1386, 1150 cm −1 for sulphate group.…”

Section: Chemistrymentioning

confidence: 99%

“…IR spectrum of compound 4 showed absorption bands at v max = 3462 cm −1 for hydroxyl group, v max = 1658 cm −1 for carbonyl group and v max = 1386, 1150 cm −1 for sulphate group. 1 H NMR spectrum showed three singlet signals at δ = 7.19, 10.33 and 11.56 ppm corresponding to H 6 of hyroxyphenyl-Scheme 1. Synthetic pathways for compounds 1-4.…”

Section: Chemistrymentioning

confidence: 99%

“…The considerable innovation has been witnessed in past three decades in the field of azo dye chemistry based on heterocyclic systems and studies in the synthesis of such derivatives have been reported [1]- [5]. Most of the recent research has focused on structural variations of existing types, for example, variations in substituent, especially on the side chains of the coupling components.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of Novel Acid Dyes with Coumarin Moiety and Their Utilization for Dyeing Wool and Silk Fabrics

Bashandy¹,

Mohamed²,

El‐Molla³

et al. 2016

OJMC

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This article describes the synthesis of some novel coumarin compounds to use as acid dyes by using compounds 1 -4 as starting materials, which were prepared by interaction of 2-hydroxybenzaldehyde with ethyl 3-oxobutanoate, diethylmalonate, 4-nitrobenzenediazonium chloride and 4-sulfobenzene-diazonium chloride, respectively. Compound 1 reacted with bromine and 2-cyanoacetohydrazide to give phenacyl bromide derivative 5 and 2-cyanoacetohydrazone derivative 6, respectively. Coupling of compound 6 with equimolar amount of 2-sulfo-4-((4-sulfophenyl) diazenyl)benzenediazonium chloride gave coumarin acid dye 8. Phenacyl bromide derivative 5 reacted with potassium cyanide in refluxing ethanol to produce compound 7, which on coupling with equimolar amount of 8-hydroxy-6-sulfonaphthalene-2-diazonium chloride and 8-hydroxy-3,6-disulfonaphthalene-1-diazonium chloride gave coumarin acid dyes 9 and 10, respectively. Interaction of compound 2 with 2-amino-5-((4-sulfophenyl)diazenyl)benzenesulfonic acid, benzene-1,4-diamine and 3,3'-dimethoxy-[1,1'-biphenyl]-4,4'-diamine in refluxing ethanol afforded compounds 11, 12 and 14, respectively. Diazonium sulphate of compounds 12 and 14 coupling with 4-amino-5-hydroxynaphthalene-2,7-disulfonic acid gave compounds 13 and 15, respectively. Cyclocondensation of compound 3 with ethyl 3-oxobutanoate, diethyl malonate and malononitrile afforded derivatives of 3-acetyl-2H-chromen-2-one 16, ethyl 2-oxo-2H-chromene-3-carboxylate 17 and 2-imino-2H-chromene-3-carbonitrile 18, respectively. Reaction of sodium benzenesulfonate deriva-* Corresponding author. M. S. Bashandy et al. 19tive 4 with ethyl 3-oxobutanoate and hydrazine hydrate gave compounds 19 and 20, respectively. The structures of the newly synthesized compounds were confirmed by elemental analysis, UV/ VIS, IR, 1 H NMR and Ms spectral data. The suitability of the prepared dyestuffs for dyeing of wool and silk fabrics has been investigated. The dyed fabric shows good light fastness, very good rubbing, perspiration, washing and excellent sublimation fastness. These dyes have been color shade from blue to violet with very good depth and levelness on fabrics. The dye bath exhaustion and fixation on fabric has been found to be very good.

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“…Various experimental and theoretical studies on the structure, tautomeric behavior, dyeing properties, and vibrational analysis of azo dyes [10][11][12][13][14][15][16][17][18][19] and their metal complexes [20][21][22] have been done. Due to their chemical significance and spectroscopic properties, hetarylazo dyes were studied extensively by spectroscopic and theoretical methods.…”

Section: Introductionmentioning

confidence: 99%

Hetarylazopyrazolone Dyes Based on Benzothiazole and Benzimidazole Ring Systems: Synthesis, Spectroscopic Investigation, and Computational Study

Aktan

Uyar

2017

Journal of Chemistry

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In this study, the synthesized coupling component 1-(2-benzothiazolyl)-3-methylpyrazol-5-one reacted with diazotised heterocyclic amines to afford six novel hetarylazopyrazolone dyes. These azo dyes based on benzothiazole and benzimidazole ring systems were characterized by spectral methods and elemental analyses. The solvatochromic behaviors of these dyes in various solvents were evaluated. The ground state geometries of the dyes were optimized using density functional theory (DFT). Solvent, acid-base, and substituent influences on the wavelength of the maximum absorption were examined in detail. Time-dependent density functional theory (TD-DFT) calculations were performed to obtain the absorption spectra of the dyes in various solvents and the results compared with experimental values. Besides, frontier molecular orbitals (FMO) analysis for the dyes is also described from the computational process.

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Synthesis of some transition metal complexes with new heterocyclic thiazolyl azo dye and their uses as sensitizers in photo reactions

Cited by 57 publications

References 40 publications

Synthesis and Characterization of New Azo 4,5-dimethyl-2-((3-((E)-1-(2-phenylhydrazono)ethyl)phenyl)diazenyl)-1H-imidazole and its Metal(II) Complexes

Synthesis and Characterization of New Azo 4,5-dimethyl-2-((3-((E)-1-(2-phenylhydrazono)ethyl)phenyl)diazenyl)-1H-imidazole and its Metal(II) Complexes

Synthesis of Novel Acid Dyes with Coumarin Moiety and Their Utilization for Dyeing Wool and Silk Fabrics

Hetarylazopyrazolone Dyes Based on Benzothiazole and Benzimidazole Ring Systems: Synthesis, Spectroscopic Investigation, and Computational Study

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