الملخص
Abstract
A heterocyclic diazo dye containing coumarin structure, which is:
7-hydroxy-4-methyl-8-(4-nitrophenylazo)-6-(4-nitrophenylazo) coumarin, has been synthesized by diazotization a double molar amount of the aromatic amine: 4-nitroaniline. Then coupling reaction of diazonium resulting salt with one molar amount of 7-hydroxy -4- methyl coumarin was done ,the purity of this dye was verified by measuring the melting point and TLC, Purified dye was characterized by spectroscopic methods such as : 1HNMR, IR
References
المراجع
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2-Cai . K , He . H , Chang . Y , Xu. W ,An Efficient and Green Route to Synthesize Azo Compounds through Methyl Nitrite, Green and Sustainable Chemistry, (2014), 4, 111-119
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Frankfurt,Germany, (2003), 685
4 -Bamoniri1. A , Pourali . A.R, and Nazifi . S.M.R, Nano Silica/ HI4as a Green and Reusable Catalyst for Synthesis of 2-Naphthol Azo Dyes under GrindingConditions, Int. J. Nanosci. Nanotechnol., 10, ,(2014), 197-203
5- Karami1. B , Kiani1. M , Application of 7 amino coumarins for the synthesis of nove and thermally stable water insoluble azo coumarin dyes Iranian Chemical Society ,6, 2015
6- L .Hongqi , L. Cai, J. Li, Y.Hu, P. Zhou, J.Zhang, Novel coumarin fluorescent dyes: Synthesis, structural characterization and recognition behavior towards Cu(II) and Ni(II), Dyes and Pigments (2011), 91, 309-316
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10 -F. Z. Haquea, M. Husain , Synthesis and spectroscopic characterization of coumarin 440 dyedoped silica gel rods, Optik 125 (2014) ,2308–2312
11-Talebniaa . F , Nourmohammadiana .F , Bastanib . S, Development of novel fluorescent offset ink based on coumarin dyes:Synthesis and properties, Progress in Organic Coatings (2014) , 77 , 1351–1359
12- M.Ozkütük , E.Ipek, B.Aydıner, S. Mamas, Z. Sefero_glu, Synthesis, spectroscopic, thermal and electrochemical studies on thiazolyl azo based disperse dyes bearing coumarin, Journal of Molecular Structure (2016), 1108, 521-532
13- T. V. Soumya, P. Thasnim, D. Bahulayan, Step-economic and cost effective synthesis of coumarin based blueemitting fluorescent dyes, Tetrahedron Letters , (2014), 55, 4643–4647
14- Gopi . C and Dhanaraju . M .D , Synthesis, characterization and anti-microbial action of novel azo dye derived from 4-Methyl 7- OH 8 Nitro coumarin,Journal of Pharmacy Research , (2011),4,1037-1038
15-Sahooa . J , Mekapb . S. K , Kumara . P. S , Synthesis, spectral characterization of some new 3-heteroaryl azo4-hydroxy coumarin derivatives and their antimicrobial evaluation, Journal of Taibah University for Science , (2015) , 9,187–195
16-Edward G. Hagop S, Irina H and Ion S,Synthesis and Characterization of new azo coumarin dye, Sci. Bull., Series B, ( 2011) ,Vol. 73, Iss. 4
17-Ibrahim M.Al Sabea and Saour Y.K,Synthesis of Nitrocoumarian Derivation and Separation of its Isomers AJPSvol ., , (2005),1,No.2
18-Swayam Sourav Sahoo, Smita Shukla , Subhangankar Nandy and Himanshu Bhusan Sahoo, Synthesis of novel coumarin derivatives and its biological evaluations , European Journal of Experimental Biology, (2012), 2 (4):899-908
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20- Qinji Peng, Mujie Li, Kuriyu Gao & Lubai Cheng , Hydrazone-Azo Tautomerism of Pyridone Azo Dyes: Part l-NMR Spectra of Tautomers m Dyes and Pigments 14 (1990) 89-99
21) Metwally, M.A.; Bondock, S.; El-Desouky, E.I.; Abdou, M. M. A facile synthesis, tautomeric structure of novel 4-arylhydrazono-3-(2-hydroxyphenyl)-2-pyrazolin-5-ones and their application as disperse dyes. Color. Technol. 2013, 129 (6), 418-424. (DOI: 10.1111/cote. 12052).
22-Abdou, M. M.; Bondock, S.; El-Desouky, E.I.; Metwally, M.A. Synthesis, spectroscopic studies and technical evaluation of novel disazo disperse dyes derived from 3-(2-hydroxyphenyl)-2-pyrazolin-5-ones for dyeing polyester fabrics. Am. J. Chem., 2013, 3 (4), 59-67. (DOI: 10.5923/j. chemistry .20130303.04).
23- Abdou, M. M. Thiophene-based azo dyes and their applications in dyes chemistry. Am. J. Chem., 2013, 3(5): 126-135. (DOI: 10.5923/j.chemistry. 20130305.02).
24- Metwally, M. A.; Bondock, S; El-Desouky, S.I.; Abdou, M.M. Synthesis, structure investigation and dyeing assessment of novel bisazo disperse dyes derived from 3-(2-hydroxyphenyl)-1-phenyl-2-pyrazolin-5-ones for dyeing polyester fabrics. J. Korean Chem. Soc., 2012, 56(3), 348-56. (DOI: 10.5923/j.chemistry.20130303.04).
25-Abdou, M. M.; Bondock, S.; El-Desouky, E.I.; Metwally, M.A. A worthy insight into the dyeing applications of azo pyrazolyl dyes. Int. J. Modern Org. Chem., 2012, 1(3): 165-92.
26- Abdou, M.M; Bondock, S.; El-Desouky, E.I.; Metwally, M.A. Synthesis, structure elucidation and application of some new azo disperse dyes derived from 4-hydroxycoumarin for dyeing polyester fabrics. Am. J. Chem., 2012, 2 (6), 347-54. (DOI: 10.5923/j.chemistry.20120206. 09).
27- Abdou, M. M.; Bondock, S.; El-Desouky, E.I. Metwally, M.A. Pyrazol-5-ones: tautomerism, synthesis and reactions. Int. J. Modern Org. Chem., 2012, 1(1): 19-54.
28- Metwally, M.A.; Bondock, S.; El-Desouky, E.I.; Abdou, M.M. Synthesis, tautomeric structure, dyeing characteristics, and antimicrobial activity of novel4-(2-arylazophenyl)-3-(2-hydroxyphenyl)-1-phenyl-2-pyrazolin-5-ones. J. Korean. Chem. Soc., 2012, 56(1), 82-91. (Doi: 10.5012/jkcs.2012.56.1.082).
1- Teimouri1 . A , Chermahini . A. N , Ghorbani . M. H , The green synthesis of new azo dyes derived from salicylic acid derivatives catalyzed via baker’s yeast and solid acid catalysis, chemija,. (2013), 24, 59–66
2-Cai . K , He . H , Chang . Y , Xu. W ,An Efficient and Green Route to Synthesize Azo Compounds through Methyl Nitrite, Green and Sustainable Chemistry, (2014), 4, 111-119
3-HUNGER, K. Industrial Dyes Chemistry, Properties, Applications,
Frankfurt,Germany, (2003), 685
4 -Bamoniri1. A , Pourali . A.R, and Nazifi . S.M.R, Nano Silica/ HI4as a Green and Reusable Catalyst for Synthesis of 2-Naphthol Azo Dyes under GrindingConditions, Int. J. Nanosci. Nanotechnol., 10, ,(2014), 197-203
5- Karami1. B , Kiani1. M , Application of 7 amino coumarins for the synthesis of nove and thermally stable water insoluble azo coumarin dyes Iranian Chemical Society ,6, 2015
6- L .Hongqi , L. Cai, J. Li, Y.Hu, P. Zhou, J.Zhang, Novel coumarin fluorescent dyes: Synthesis, structural characterization and recognition behavior towards Cu(II) and Ni(II), Dyes and Pigments (2011), 91, 309-316
7-S. B. Phadtare, K. J. Jarag, G. S. Shankarling , Greener protocol for one pot synthesis of coumarin styryl dyes, Dyes and Pigments, (2013) , 97, 105-112
8- Ibrayeva . N. Kh , Seliverstovaa .E. V , Alekseevab V. I , Marininab L. E. , and L. P. Savvina, Preparation and Photophysical Properties of Thin Films of Coumarin Dyes, Russian Journal of Physical Chemistry 2013, 87, pp 1234–1238
9- Oprea . C. I , Panait . P , Cimpoesu . F, Ferbinteanu . M and Gîrţu . M. A , Density Functional Theory (DFT) Study of Coumarin-basedn Dyes Adsorbed on TiO2 Nanoclusters Applications ton Dye-Sensitized Solar Cells, Materials , (2013), 6, 2372-2392
10 -F. Z. Haquea, M. Husain , Synthesis and spectroscopic characterization of coumarin 440 dyedoped silica gel rods, Optik 125 (2014) ,2308–2312
11-Talebniaa . F , Nourmohammadiana .F , Bastanib . S, Development of novel fluorescent offset ink based on coumarin dyes:Synthesis and properties, Progress in Organic Coatings (2014) , 77 , 1351–1359
12- M.Ozkütük , E.Ipek, B.Aydıner, S. Mamas, Z. Sefero_glu, Synthesis, spectroscopic, thermal and electrochemical studies on thiazolyl azo based disperse dyes bearing coumarin, Journal of Molecular Structure (2016), 1108, 521-532
13- T. V. Soumya, P. Thasnim, D. Bahulayan, Step-economic and cost effective synthesis of coumarin based blueemitting fluorescent dyes, Tetrahedron Letters , (2014), 55, 4643–4647
14- Gopi . C and Dhanaraju . M .D , Synthesis, characterization and anti-microbial action of novel azo dye derived from 4-Methyl 7- OH 8 Nitro coumarin,Journal of Pharmacy Research , (2011),4,1037-1038
15-Sahooa . J , Mekapb . S. K , Kumara . P. S , Synthesis, spectral characterization of some new 3-heteroaryl azo4-hydroxy coumarin derivatives and their antimicrobial evaluation, Journal of Taibah University for Science , (2015) , 9,187–195
16-Edward G. Hagop S, Irina H and Ion S,Synthesis and Characterization of new azo coumarin dye, Sci. Bull., Series B, ( 2011) ,Vol. 73, Iss. 4
17-Ibrahim M.Al Sabea and Saour Y.K,Synthesis of Nitrocoumarian Derivation and Separation of its Isomers AJPSvol ., , (2005),1,No.2
18-Swayam Sourav Sahoo, Smita Shukla , Subhangankar Nandy and Himanshu Bhusan Sahoo, Synthesis of novel coumarin derivatives and its biological evaluations , European Journal of Experimental Biology, (2012), 2 (4):899-908
19-P. S. Song and W.H. Gordon., J. Phys. Chem., 74 (24), 1970,4234
20- Qinji Peng, Mujie Li, Kuriyu Gao & Lubai Cheng , Hydrazone-Azo Tautomerism of Pyridone Azo Dyes: Part l-NMR Spectra of Tautomers m Dyes and Pigments 14 (1990) 89-99
21) Metwally, M.A.; Bondock, S.; El-Desouky, E.I.; Abdou, M. M. A facile synthesis, tautomeric structure of novel 4-arylhydrazono-3-(2-hydroxyphenyl)-2-pyrazolin-5-ones and their application as disperse dyes. Color. Technol. 2013, 129 (6), 418-424. (DOI: 10.1111/cote. 12052).
22-Abdou, M. M.; Bondock, S.; El-Desouky, E.I.; Metwally, M.A. Synthesis, spectroscopic studies and technical evaluation of novel disazo disperse dyes derived from 3-(2-hydroxyphenyl)-2-pyrazolin-5-ones for dyeing polyester fabrics. Am. J. Chem., 2013, 3 (4), 59-67. (DOI: 10.5923/j. chemistry .20130303.04).
23- Abdou, M. M. Thiophene-based azo dyes and their applications in dyes chemistry. Am. J. Chem., 2013, 3(5): 126-135. (DOI: 10.5923/j.chemistry. 20130305.02).
24- Metwally, M. A.; Bondock, S; El-Desouky, S.I.; Abdou, M.M. Synthesis, structure investigation and dyeing assessment of novel bisazo disperse dyes derived from 3-(2-hydroxyphenyl)-1-phenyl-2-pyrazolin-5-ones for dyeing polyester fabrics. J. Korean Chem. Soc., 2012, 56(3), 348-56. (DOI: 10.5923/j.chemistry.20130303.04).
25-Abdou, M. M.; Bondock, S.; El-Desouky, E.I.; Metwally, M.A. A worthy insight into the dyeing applications of azo pyrazolyl dyes. Int. J. Modern Org. Chem., 2012, 1(3): 165-92.
26- Abdou, M.M; Bondock, S.; El-Desouky, E.I.; Metwally, M.A. Synthesis, structure elucidation and application of some new azo disperse dyes derived from 4-hydroxycoumarin for dyeing polyester fabrics. Am. J. Chem., 2012, 2 (6), 347-54. (DOI: 10.5923/j.chemistry.20120206. 09).
27- Abdou, M. M.; Bondock, S.; El-Desouky, E.I. Metwally, M.A. Pyrazol-5-ones: tautomerism, synthesis and reactions. Int. J. Modern Org. Chem., 2012, 1(1): 19-54.
28- Metwally, M.A.; Bondock, S.; El-Desouky, E.I.; Abdou, M.M. Synthesis, tautomeric structure, dyeing characteristics, and antimicrobial activity of novel4-(2-arylazophenyl)-3-(2-hydroxyphenyl)-1-phenyl-2-pyrazolin-5-ones. J. Korean. Chem. Soc., 2012, 56(1), 82-91. (Doi: 10.5012/jkcs.2012.56.1.082).