• Archives of Pharmacal Research
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• v.14 no.3
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• pp.237-241
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• 1991

The tautomerism in 3-phenyl-4-arylazo-5-isoxazolones 1 was examined by $^1H-NMR$ spectra of $^15N-labeled$ compound and by HMO method. Both spectra data $(^1H-NMR\;and\;IR)$ and bonding energies are in support of the assignment of the hydrazone structure to such compounds. It is further shown that intermolecular and intramolecular hydrogen bondings favor the hydrazone tautomer.

• Textile Coloration and Finishing
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• v.23 no.3
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• pp.163-168
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• 2011

In this article, we synthesized an azo dye rotaxane containing bis(8-hydroxyquinoline) group and its polymeric metal complex with zinc. The azo dye rotaxane exhibits high pH sensitivity, solvatochromism and zinc (II) ion sensings in aqueous solution. These behaviors came from the tautomeric equilibrium between azo-hydrazone tautomers and the formation of extended conjugation. The structure of polymeric zinc complexed dye rotaxane was confirmed with NMR and FT-IR measurements. The existence of CD rings, provided by dye rotaxane formation, was found to be very beneficial in improving aqueous solubility of polymeric metal complex.

• Journal of the Korean Chemical Society
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• v.56 no.3
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• pp.348-356
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• 2012

In an attempt to find a new class of bisazo disperse dyes with better dyeing properties, a series of novel bisazo dyestuffs based on 4-arylhydrazono-3-(2'-hydroxyphenyl)-1-phenyl-2-pyrazolin-5-ones $\mathbf{3a-f}$ were prepared by diazocoupling of p-nitrophenyl diazonium chloride with 4-arylhydrazono-3-(2'-hydroxyphenyl)-1-phenyl-2-pyrazolin-5-ones $\mathbf{2a-f}$. Compounds $\mathbf{3a-f}$ were subsequently reacted with acetic anhydride in the presence of p-toluenesulfonic acid afford the corresponding O-acetyl derivatives $\mathbf{4a-f}$. The latter products as well as spectral data indicated that compounds $\mathbf{3a-f}$ exist predominantly in the azo-hydrazone tautomeric form (H) as the ZE-configuration. Additionally, two series of the synthesized dyes $\mathbf{3a-f}$ and $\mathbf{4a-f}$ were applied as disperse dyes for dyeing polyester fabrics and their fastness properties were evaluated. Also the position of color in CIELAB coordinates ($L^*$, $a^*$, $b^*$, $H^*$, $C^*$*) was assessed.

• Journal of the Korean Chemical Society
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• v.56 no.1
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• pp.82-91
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• 2012

Novel azopyrazolin-5-one dyes 4a-f were synthesized by the regioselective reaction of phenylhydrazine with 2,3,4-chromantrione-3-arylhydrazones 2a-f. The acid dissociation constants $pK_a$ for the series prepared were determined and correlated by the Hammett equation. The results of such correlation together with the spectral data indicated that the studied compounds exist predominantly in the hydrazone keto structure, (D) as the Z-configuration. The dyes were applied to polyester fabrics, affording orange-yellow shades and assessments of their dyeing performance are considered. Further, the compounds 4a-f were screened for their antimicrobial activity against various microorganisms.

• Journal of the Korean Chemical Society
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• v.65 no.2
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• pp.93-105
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• 2021

Mononuclear Cu(II), Ni(II), Co(II), Mn(II), Zn(II), Fe(III), Ru(III), and UO2(II) complexes of 2-hydroxy-4-(p-tolyldiazenyl)benzylidene)-2-(p-tolylamino)acetohydrazide (H2L) were prepared by direct method. The ligand and its complexes were isolated in solid state and characterized by analytical techniques such as elemental and thermal analyses, molar conductance, magnetic susceptibility measurements and spectroscopic techniques such as UV-Visible, IR, 1H-NMR and 13C-NMR. The spectral data indicated that the ligand acted as neutral/monobasic bidentate or monobasic/dibasic tridentate ligand bonded to the metal ions through the oxygen atom of ketonic or enolic carbonyl group, azomethine nitrogen atom and deprotonated/protonated phenolic oxygen atom forming either tetragonally distorted octahedral or octahedral. Antimicrobial activities of the ligand and its complexes were evaluated against Escherichia coli, Bacillus subtilis and Aspergillus niger by well diffusion method. The results of antifungal activity showed that the Fe(III) complex (10) exhibited higher antifungal against Aspergillus niger than the other complexes. However, the results of antibacterial activity revealed that Cu(II) complex (4) is the most active against Escherichia coli while the Cu(II) complex (5) and Fe(III) complex (10) exhibited higher antibacterial effect on Bacillus subtilis than the other complexes.

• Proceedings of the Korean Society of Dyers and Finishers Conference
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• 2011.03a
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• pp.32-32
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• 2011

염료의 포토크로미즘은 빛을 받았을 때, 염료의 분자구조가 변환되어 흡수파장이 달라지고 결과적으로 원래 색과 다른 색상을 나타내는 현상을 말한다. 대부분의 Golden yellow 색상을 나타내는 아조계 반응성염료는 Trans-Cis 간의 이성질체 전환을 통해 포토크로미즘 현상을 나타내며, 가역적으로 복색되기는 하지만 상업적으로 많은 문제와 불편을 초래한다. 한편 pyrazolone계 아조염료는 azo form 보다는 hydrazone form으로 더 많이 존재하는 것으로 알려져 있으며, 이로인해 상대적으로 Trans-Cis 이성질화가 잘 일어나지 않아 포토크로미즘 현상이 잘 일어나지 않을 것으로 기대된다. 이 연구에서는 3종의 pyrazolone계 golden yellow 반응성 염료를 합성하고, 합성한 염료를 면직물에 염색하여 염색성 및 견뢰도를 평가하였다. 또한 시판되고 있는 아조계 golden yellow 반응성 염료 4종을 선정하여 역시 염색성과 견뢰도 특성을 알아보았다. 그리고 7가지 염료의 광변색 특성을 조사하기 위해 포토크로미즘 평가방법인 ISO 105-B05법 및 이전 연구에서 제안된 광변색 평가방법을 사용하였다. ISO 105-B05법은 표준청색염포가 grey scale 4등급이 되는 시간을 구한 다음 이 시간의 1/4시간동안 조사한 후 포토크로미즘을 평가하는 것이며, 후자의 경우는 4시간동안 광조사된 시험편을 측색하고 시간에 따른 복색되는 정도를 평가한다. 합성한 pyrazolone계 염료들은 394-408nm의 최대흡수파장은 나타내었다. 7종의 yellow 반응성 염료들은 모두 면직물에 우수한 염색성 및 build-up성을 나타내었으며, 대체적으로 양호한 견뢰도를 얻었다. 또한 광변색 특성 평가결과 모든 염료들은 ISO 평가방법에 대하여 non-photochromic 특성으로 나타났으나, 다른 광변색 평가 결과 일부 염료들에 있어서 photochromic 특성이 있는 것으로 나타나 평가방법에 따라 차이를 보였다.