A novel fluorescent bisazomethine dye derived from 3-hydroxyquinoxaline-2-carboxaldehyde and 2,3-diaminomaleonitrile

Arun, V.; Robinson, P.P.; Manju, S.; Leeju, P.; Varsha, G.; Digna, V.; Yusuff, K. K. Mohammed

doi:10.1016/j.dyepig.2009.01.010

Cited by 36 publications

(10 citation statements)

References 47 publications

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“…(shoulder) and 424 nm. The electronic spectrum of the species corresponding to the major peak is due to the amide form and that corresponding to the minor peak is due to the iminol from [23]. Thus the Schiff base exhibits prototropic tautomerism and exists in the predominant amide form.…”

Section: Resultsmentioning

confidence: 99%

“…The highest energy absorption bands in the solution spectra (all solvents) are assigned to p / p* transitions by virtue of their large molar extinction coefficients ( Table 1). The n / p* transitions of the quinoxaline ring appears as a shoulder band around 355 nm [23]. The band centered on 420 nm is due to the n / p* transitions of the azomethine group.…”

Section: Resultsmentioning

confidence: 99%

“…The solid state diffuse reflectance spectrum (DRS) of HQCAAP shows bands at 253 nm, 354 nm, 482 nm and 625 nm (shoulder). The first one is due to the p / p* transitions of the heterocyclic quinoxaline ring and the second one is due to the n / p* transition of the eC] Ne group in quinoxaline ring [23]. The azomethine n / p* transition appears at 482 nm.…”

Section: Resultsmentioning

confidence: 99%

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The tautomerism, solvatochromism and non-linear optical properties of fluorescent 3-hydroxyquinoxaline-2-carboxalidine-4-aminoantipyrine

et al. 2010

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a b s t r a c tThe Schiff base, 3-hydroxyquinoxaline-2-carboxalidine-4-aminoantipyrine, was synthesized by the condensation of 3-hydroxyquinoxaline-2-carboxaldehyde with 4-aminoantipyrine. HPLC, FT-IR and NMR spectral data revealed that the compound exists predominantly in the amide tautomeric form and exhibits both absorption and fluorescence solvatochromism, large stokes shift, two electron quasireversible redox behaviour and good thermal stability, with a glass transition temperature of 104 C. The third-order non-linear optical character was studied using open aperture Z-scan methodology employing 7 ns pulses at 532 nm. The third-order non-linear absorption coefficient, b, was 1.48 Â 10 À6 cm W À1 and the imaginary part of the third-order non-linear optical susceptibility, Im c (3) , was 3.36 Â 10 À10 esu. The optical limiting threshold for the compound was found to be 340 MW cm À2 .

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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The tautomerism, solvatochromism and non-linear optical properties of fluorescent 3-hydroxyquinoxaline-2-carboxalidine-4-aminoantipyrine

et al. 2010

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“…Maclachlan et al [12] for the �rst time reported the crystal structures of Schiff base derived from DAMN and salicylaldehyde with some metal complexes. A novel bisazomethine Schiff base formed by the condensation of 3-hydroxyquinoxaline-2-carboxaldehyde and 2,3-diaminomaleonitrile has been carried out by Arun et al [13]. e studies revealed that the compound exists in two major tautomeric forms and the Schiff base exhibits positive absorption and �uorescent solvatochromism and displays dual �uorescence with large stoke shi�s.…”

Section: Introductionmentioning

confidence: 99%

Studies on Synthesis and Spectral Characterization of Some Transition Metal Complexes of Azo-Azomethine Derivative of Diaminomaleonitrile

Anitha¹,

Sheela

Tharmaraj

et al. 2013

International Journal of Inorganic Chemistry

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New complexes of 2,3-bis(5-(4-chlorophenyl)diazenyl)-2-hydroxybenzylideneamino)maleonitrile (CDHBDMN) with VO(II), Mn(II), Co(II), Ni(II), Cu(II), and Zn(II) were synthesized and characterized by analytical and physicochemical techniques, that is, elemental analyses, molar conductivity, UV, IR, EPR, 1 H-NMR spectra, magnetic susceptibility and also by aid of scanning electron microscopy (SEM), nonlinear optical study (NLO), �uorescence spectral studies, and solvatochromic behaviors. Electronic and magnetic susceptibility measurements of the complexes indicate square pyramidal geometry for VO(II), octahedral for Ni(II), and square planar geometry for all the other complexes. e EPR spectral data provide information about their structures on the basis of Hamiltonian parameters and the degree of covalency. ese metal complexes were also tested for their antibacterial and antifungal activities to assess their inhibiting potential. Metal-mediated �uorescence enhancement is observed on complexation of the azo Schiff base ligand. e synthesized compounds were investigated for nonlinear optical properties, and the surface morphology of the Cu(II) complex was studied by scanning electron microscopy.

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“…The synthesis of the Schiff base ligand involved two steps: synthesis of 3‐hydroxyquinoxaline‐2‐carboxaldehyde followed by its condensation with 2‐amino‐5‐chlorobenzophenone. The aldehyde was synthesized by following a procedure reported earlier . The ligand, 3‐{[(2‐benzoyl‐4‐chlorophenyl)imino]methyl}quinoxalin‐2(1 H )‐one ( L ), was synthesized by adopting the following procedure.…”

Section: Methodsmentioning

confidence: 99%

Transition metal complexes of a novel quinoxaline‐based tridentate ONO donor ligand: synthesis, spectral characterization, thermal, in vitro pharmacological and molecular modeling studies

Dhanaraj

Johnson

2016

Applied Organom Chemis

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Co(II), Ni(II), Cu(II) and Zn(II) complexes of a novel tridentate heterocyclic ligand, 3‐{[(2‐benzoyl‐4‐chlorophenyl)imino]methyl}quinoxalin‐2(1H)‐one, have been synthesized. The ligand and the metal complexes were characterized using elemental analysis, molar conductance and magnetic susceptibility measurements, and UV–visible, Fourier transform infrared, 1H NMR, 13C NMR, electron spin resonance and DART mass spectral data. The ligand behaves as a tridentate one, coordinating through two oxygen atoms from two keto groups and through the azomethine nitrogen atom. The thermal properties of the newly synthesized compounds were determined using thermogravimetric analysis. The ligand and its metal complexes were subjected to powder X‐ray diffraction analysis by which average crystallite size and unit cell parameters were calculated. The electrochemical behaviour of the compounds was studied using cyclic voltammetry. The ligand and the metal complexes were screened for their in vitro antimicrobial activities against the bacterial strains E. coli, K. pneumoniae, S. pneumoniae and S. aureus and the fungal species A. niger, A. flavus, P. chrysogenum and R. stolonifer. DNA binding, DNA cleavage and antioxidant activities of the compounds were also evaluated. The compounds bind with DNA through groove binding. The Cu(II) and Zn(II) complexes exhibit higher superoxide anion and hydrogen peroxide scavenging activities, respectively. The Cu(II) complex exhibits better anticancer activity against the MCF7 cell line. The compounds were subjected to molecular docking study against B‐DNA dodecamer d(CGCGAATTCGCG)2 and vascular endothelial growth factor receptor kinase to justify the experimental DNA binding and MTT assay. Density functional theory studies were used to optimize the geometry of the compounds and to calculate the nonlinear optical properties. Copyright © 2016 John Wiley & Sons, Ltd.

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A novel fluorescent bisazomethine dye derived from 3-hydroxyquinoxaline-2-carboxaldehyde and 2,3-diaminomaleonitrile

Cited by 36 publications

References 47 publications

The tautomerism, solvatochromism and non-linear optical properties of fluorescent 3-hydroxyquinoxaline-2-carboxalidine-4-aminoantipyrine

The tautomerism, solvatochromism and non-linear optical properties of fluorescent 3-hydroxyquinoxaline-2-carboxalidine-4-aminoantipyrine

Studies on Synthesis and Spectral Characterization of Some Transition Metal Complexes of Azo-Azomethine Derivative of Diaminomaleonitrile

Transition metal complexes of a novel quinoxaline‐based tridentate ONO donor ligand: synthesis, spectral characterization, thermal, in vitro pharmacological and molecular modeling studies

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