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3-Amino-5-Hidroksi-1H-Pirazol Bazlı Bazı Yeni Disazo Boyarmaddelerinin Sentezi ve Spektroskopik Özellikleri

Year 2021, Volume: 16 Issue: 1, 189 - 199, 27.05.2021
https://doi.org/10.29233/sdufeffd.887728

Abstract

Bu çalışmada, yeni bir dizi 3-amino-5-hidroksi-1H-pirazol türevi boyarmadde sentezlendi ve karakterize edildi. Bu maksatla, m- ve o- sübstitüe anilin türevleri öncelikle diazolandı, elde edilen bileşikler 3-amino krotononitril ile kenetlendi. Elde edilen ürün (1a-h) hidrazin monohidrat ile etkileştirilerek 5-amino-4-arilazo-3-metil-1H-pirazoller (2a-h) sentezlendi. Sonrasında 5-amino-4-arilazo-3-metil-1H-pirazoller diazolandı ve 3-amino-5-hidroksi-1H-pirazol ile kenetlenerek 8 adet yeni disazo boyarmaddesi (3a-h) sentezlenmiş oldu. Elde edilen sekiz boyarmaddenin yapısı Fourier dönüşümlü infrared spektroskopisi (FT-IR), Nükleer manyetik rezonans spektroskopisi (1H-NMR), Ultraviyole görünür bölge absorpsiyon spektroskopisi (UV-Vis) ve element analizi gibi çeşitli spektrofotometrik yöntemlerle belirlendi. Altı farklı çözücüde boyarmaddelerin maksimum absorpsiyon dalga boyları belirlendi ve absorpsiyon spektrumları üzerine asit-baz etkisi incelendi. Bu çalışma sonunda tekstil ve azo boyarmadde literatürüne 8 adet yeni aminopirazol türevi disazo boyarmaddeleri kazandırıldı.

Supporting Institution

Pamukkale Üniversitesi Bilimsel Araştırma Projesi Koordinasyon Birimi

Project Number

2016 HZDP 036

Thanks

Bu çalışma Pamukkale Üniversitesi Bilimsel Araştırma Projesi Koordinasyon Birimi tarafından kabul edilen 2016 HZDP 036 numaralı proje kapsamında gerçekleştirilmiştir. Pamukkale Üniversitesi ve Bilimsel Araştırma Projesi Koordinasyon Birimine teşekkür ederim.

References

  • [1] J. F. Dawson, ‘‘Developments in disperse dyes,’’ Color. Technol., 9, 25–35, 1978.
  • [2] H. Zollinger, ‘‘Color Chemistry: Synthesis, Properties and Application of Organic Dyes and Pigments,’’ third ed. Wiley-VCH, Weinheim, 161-167, 2003.
  • [3] H. Yousefi, A. Yahyazadeh, E. O. Moradi Rufchahi, M. Rassa, ‘‘Synthesis, spectral properties, biological activity and application of new 4-(benzyloxy)phenol derived azo dyes for polyester fiber dyeing,’’ J. Mol. Liq., 180, 51-58, 2013.
  • [4] H. F. Rizk, S. A. Ibrahim, M. A. El-Borani, ‘‘Synthesis, fastness properties, color assessment and antimicrobial activity of some azo reactive dyes having pyrazole moiety,’’ Dyes and Pigments, 112, 86-92, 2015.
  • [5] L. He, L. Lu, S. Zhang, H. S. Freeman, ‘‘Synthesis and application of yellow azoanthraquinone disperse dyes for polylactide fibres,’’ Color. Technol., 126(2), 92-96, 2010.
  • [6] M. A. Metwally, E. Abdel-latif, F. A. Amer, G. Kaupp, ‘‘Synthesis of new 5-thiazolyl azo-disperse dyes for dyeing polyester fabrics,’’ Dyes and Pigments, 60(3), 249-264, 2004.
  • [7] N. M. Parekh, S. K. Sahoo, K. C. Maheria, ‘‘Quantum chemical studies and dyeing performance of some novel benzoquinoline based heterocyclic monoazo dyes on polyester fiber,’’ Dyes and Pigments, 95(1), 142-148, 2012.
  • [8] H. Z. Shams, M. H. Helal, F. Mohamed, S. A. Abd-Elhafiz, ‘‘A novel synthesis of 1-oxo-thieno [3ʹ, 2ʹ-3, 4] pyrazolo [1, 2-a] pyrazole azo dye systems for dyeing of synthetic and modified cellulose fibers,’’ Pigment Resin Technol., 30(3), 158-167, 2001.
  • [9] F. Karcı, A. Demirçalı, F. Karcı, I. Kara, F. Ucun, ‘‘The synthesis, spectroscopic properties and theoretical calculation of some novel disperse disazo dyes derived from 3-amino-5-hydroxy-1-phenylpyrazole,’’ J. Mol. Struct., 935, 19-26, 2009.
  • [10] J. H. Choi, J. Y. Choi, Y. Lee, A. D. Towns, C. Yoon, ‘‘Novel azo dyes derived from phthalimide. Part 2: dyeing properties and colour fastness on polyester fibres,’’ Color. Technol., 124(6), 364-369, 2008.
  • [11] A. Z. Sayed, M. S. Aboul-Fetouh, H. S. Nassar, ‘‘Synthesis, biological activity and dyeing performance of some novel azo disperse dyes incorporating pyrazolo [1, 5-a] pyrimidines for dyeing of polyester fabrics,’’ J. Mol. Struct., 1010, 146–151, 2012.
  • [12] G. H. Elgemeie, M. H. Helal, H. M. El-Sayed, ‘‘Recent trends in synthesis and application of nitrogen heterocyclic azo dyes,’’ Pigment Resin Technol., 30(4), 210-228, 2001.
  • [13] J. Mikroyannidis, D. Tsagkournos, P. Balraju, G. Sharma, ‘‘Low band gap dyes based on 2-styryl-5-phenylazo-pyrrole: synthesis and application for efficient dyesensitized solar cells,’’ J. Power Sources, 196, 4152–4161, 2011.
  • [14] F. Ruyffelaere, V. Nardello, R. Schmidt, J. M. Aubry, ‘‘Photosensitizing properties and reactivity of aryl azo naphtol dyes towards singlet oxygen,’’ J Photochem Photobiol A: Chem., 183, 98–105, 2006.
  • [15] O. A. Adegoke, T. E. Adesuji, O. E. Thomas, ‘‘Novel colorimetric sensors for cyanide based on azo-hydrazone tautomeric skeletons,’’ Spectrochim Acta A Mol Biomol Spectrosc., 128, 147–152, 2014.
  • [16] P. J. Coelho, L. M. Carvalho, A. M. C. Fonseca, M. M. M. Raposo, ‘‘Photochromic properties of thienylpyrrole azo dyes in solution,’’ Tetrahedron Lett., 47, 3711–3714, 2006.
  • [17] E. Pevzner, B. Ehrenberg, ‘‘Principal component analysis of the absorption and resonance Raman spectra of the metallochromic indicator antipyrylazo III,’’ Spectrochim Acta A Mol Biomol Spectrosc., 56, 637–651, 2000.
  • [18] A. Y. Al-Ahmad, Q. M. A. Hassan, H. A. Badran, K. A. Hussain, ‘‘Investigating some linear and nonlinear optical properties of the azo dye (1-amino-2-hydroxy naphthalin sulfonic acid-[3-(4-azo)]-4-amino diphenyl sulfone),’’ Opt Laser Technol., 44(5), 1450–1455, 2012.
  • [19] M. Erfantalab, H. Khanmohammadi, ‘‘New 1, 2, 4-triazole-based azo–azomethine dye. Part III: synthesis, characterization, thermal property, spectrophotometric and computational studies,’’ Spectrochim Acta A. Mol Biomol Spectrosc., 125, 345–352, 2014.
  • [20] F. Yıldırım, A. Demirçalı, F. Karcı, A. Bayrakdar, P. T. Taşlı, H. H. Kart, ‘‘New coumarin-based disperse disazo dyes: Synthesis, spectroscopic properties and theoretical calculations,’’ J. Mol Struc., 223, 557-565, 2016.
  • [21] M. Yazdanbakhsh, H. Yousefi, M. Mamaghani, E. Moradi, M. Rassa, H. Pouramir, ‘‘Synthesis, spectral characterization and antimicrobial activity of some new azo dyes derived from 4, 6-dihydroxypyrimidine,’’ J. Mol. Liq., 169, 21–26, 2012.
  • [22] F. Karcı, N. Şener, M. Yamaç, İ. Şener, A. Demirçalı, ‘‘The synthesis, antimicrobial activity and absorption characteristics of some novel heterocyclic disazo dyes,’’ Dyes and Pigments, 80, 47–52, 2009. [23] H. Xu, X. Zeng, ‘‘Synthesis of diaryl-azo derivatives as potential antifungal agents,’’ Bioorg Med Chem Lett., 20(14), 4193–4195, 2010.
  • [24] T. I. El-Emary, S. A. A. El-Mohsen, ‘‘Multi-component one-pot synthesis and antimicrobial activities of 3-Methyl-1,4-diphenyl-7-thioxo-4, 6, 8, 9-tetrahydro-pyrazolo[5, 4-b] pyrimidino [5, 4-e] pyridine-5-one and related derivatives,’’ Molecules, 17, 14464–14483, 2012
  • [25] A. P. Acharya, R. D. Kamble, S. V. Hese, S. N. Kadam, R. N. Gacche, B. S. Dawane, ‘‘Eco-friendly synthesis of novel indeno-pyrazole derivatives and their in-vitro antimicrobial screening,’’ Org. Commun, 7(2), 68-76, 2014.
  • [26] S. G. Alegaon, K. R. Alagawadi, M. Garg, K. Dushyant, D. Vinod, ‘‘1, 3, 4-Trisubstituted pyrazole analogues as promising anti-inflammatory agents,’’ Bioorg Chem., 54, 51–59, 2014.
  • [27] P. D. Gokulan, B. Jayakar, V. Alagarsamy, V. R. Solomon, ‘‘Synthesis and Pharmacological Investigation of 5-Substituted-3-Methylsulfanyl-1H-Pyrazole-4-Carboxylic Acid Ethyl Esters as New Analgesic and anti-Inflammatory Agents,’’ Arzneimittelforschung, 62, 457–462, 2012.
  • [28] H. M. Faidallah, M. M. Al-Mohammadi, K. A. Alamry, K. A. Khan, ‘‘Synthesis and Biological Evaluation of Fluoropyrazolesulfonylurea and Thiourea Derivatives as Possible AntidiabeticAgents,’’J. Enzyme Inhib. Med. Chem., 31, 157–163, 2016.
  • [29] A.R. Ali, E.R. El-Bendary, M. A. Ghaly, I. A. Shehata, ‘‘Synthesis, in vitro anticancer evaluation and in silico studies of novel imidazo [2, 1-b] thiazole derivatives bearing pyrazole moieties,’’ Eur J Med Chem., 75, 492–500, 2014.
  • [30] M. Abdel-Aziz, GE-DA Abuo-Rahma, AA Hassan, ‘‘Synthesis of novel pyrazole derivatives and evaluation of their antidepressant and anticonvulsant activities,’’ Eur J Med Chem., 44, 3480–3487, 2009
  • [31] V. Pathak, H. K. Maurya, S. Sharma, K. K. Srivastava, A. Gupta, ‘‘Synthesis and biological evaluation of substituted 4, 6-diarylpyrimidines and 3, 5-diphenyl-4, 5-dihydro-1H-pyrazoles as anti-tubercular agents,’’ Bioorg Med Chem Lett., 24, 2892–2896, 2014
  • [32] F. Yıldırım, A. Demirçalı, P. T. Taşlı, F. Karcı, ‘‘New disazo dyes derived from aminopyrazoles: synthesis, spectroscopic properties, computational study and structural properties’’ Coloration Technology, baskıda, 2021.
  • [33] M. H. Elnagdi, M. M. M. Sallam, H. M. Fahmy, S. A. M. Ibrahim, M. A. M. Elias, ‘‘Reactions with the Arylhydrazones of α-Cyanoketones: The Structure of 2-Arylhydrazono-3-ketimino-nitriles,’’ Helv Chim.Acta., 59(2), 551-557, 1976.
  • [34] M. H. Elnagdi, G. E. H. Elgemeie, F. A. E. Abd-Ellal, ‘‘Recent Developments in the Synthesis of Pyrazole Derivative,’’ Heterocycles, 23(12), 3121- 3153, 1985.
  • [35] F. Karcı, ‘‘Synthesis of disazo dyes derived from heterocyclic components,’’ Color Technol., 121, 275-280, 2005.
  • [36] F. Karcı, A. Demirçalı, ‘‘Synthesis of disazo pyrazolo[1,5-a]pyrimidines,’’ Dyes and Pigments, 74, 288-297, 2007.

Synthesis and Spectroscopic Properties of Some New Disazo Dyes Based on 3-Amino-5-Hydroxy-1H-Pyrazole

Year 2021, Volume: 16 Issue: 1, 189 - 199, 27.05.2021
https://doi.org/10.29233/sdufeffd.887728

Abstract

In this study, a new series of 3-amino-5-hydroxy-1H-pyrazole derivative dyes were synthesized and characterized. For this purpose, firstly the m- and o- substituted aniline derivatives were diazotised, the resulting compounds were coupled with 3-amino crotononitrile. 5-amino-4-arylazo-3-methyl-1H-pyrazoles (2a-h) were synthesized by reacting the obtained product (1a-h) with hydrazine monohydrate. Subsequently, the 5-amino-4-arylazo-3-methyl-1H-pyrazoles were diazotised and coupled with 3-amino-5-hydroxy-1H-pyrazole to synthesize 8 new disazo dyes (3a-h). The structure of the eight dyes obtained were determined by various spectrophotometric methods such as Fourier transform infrared spectroscopy (FT-IR), Nuclear magnetic resonance spectroscopy (1H-NMR), Ultraviolet visible region absorption spectroscopy (UV-Vis) and elemental analysis. The maximum absorption wavelengths of the dyes in six different solvents were determined and the acid-base effects on the absorption spectra were investigated. At the end of this study, 8 new aminopyrazole derivative disazo dyes were introduced to the textile and azo dyestuff literature.

Project Number

2016 HZDP 036

References

  • [1] J. F. Dawson, ‘‘Developments in disperse dyes,’’ Color. Technol., 9, 25–35, 1978.
  • [2] H. Zollinger, ‘‘Color Chemistry: Synthesis, Properties and Application of Organic Dyes and Pigments,’’ third ed. Wiley-VCH, Weinheim, 161-167, 2003.
  • [3] H. Yousefi, A. Yahyazadeh, E. O. Moradi Rufchahi, M. Rassa, ‘‘Synthesis, spectral properties, biological activity and application of new 4-(benzyloxy)phenol derived azo dyes for polyester fiber dyeing,’’ J. Mol. Liq., 180, 51-58, 2013.
  • [4] H. F. Rizk, S. A. Ibrahim, M. A. El-Borani, ‘‘Synthesis, fastness properties, color assessment and antimicrobial activity of some azo reactive dyes having pyrazole moiety,’’ Dyes and Pigments, 112, 86-92, 2015.
  • [5] L. He, L. Lu, S. Zhang, H. S. Freeman, ‘‘Synthesis and application of yellow azoanthraquinone disperse dyes for polylactide fibres,’’ Color. Technol., 126(2), 92-96, 2010.
  • [6] M. A. Metwally, E. Abdel-latif, F. A. Amer, G. Kaupp, ‘‘Synthesis of new 5-thiazolyl azo-disperse dyes for dyeing polyester fabrics,’’ Dyes and Pigments, 60(3), 249-264, 2004.
  • [7] N. M. Parekh, S. K. Sahoo, K. C. Maheria, ‘‘Quantum chemical studies and dyeing performance of some novel benzoquinoline based heterocyclic monoazo dyes on polyester fiber,’’ Dyes and Pigments, 95(1), 142-148, 2012.
  • [8] H. Z. Shams, M. H. Helal, F. Mohamed, S. A. Abd-Elhafiz, ‘‘A novel synthesis of 1-oxo-thieno [3ʹ, 2ʹ-3, 4] pyrazolo [1, 2-a] pyrazole azo dye systems for dyeing of synthetic and modified cellulose fibers,’’ Pigment Resin Technol., 30(3), 158-167, 2001.
  • [9] F. Karcı, A. Demirçalı, F. Karcı, I. Kara, F. Ucun, ‘‘The synthesis, spectroscopic properties and theoretical calculation of some novel disperse disazo dyes derived from 3-amino-5-hydroxy-1-phenylpyrazole,’’ J. Mol. Struct., 935, 19-26, 2009.
  • [10] J. H. Choi, J. Y. Choi, Y. Lee, A. D. Towns, C. Yoon, ‘‘Novel azo dyes derived from phthalimide. Part 2: dyeing properties and colour fastness on polyester fibres,’’ Color. Technol., 124(6), 364-369, 2008.
  • [11] A. Z. Sayed, M. S. Aboul-Fetouh, H. S. Nassar, ‘‘Synthesis, biological activity and dyeing performance of some novel azo disperse dyes incorporating pyrazolo [1, 5-a] pyrimidines for dyeing of polyester fabrics,’’ J. Mol. Struct., 1010, 146–151, 2012.
  • [12] G. H. Elgemeie, M. H. Helal, H. M. El-Sayed, ‘‘Recent trends in synthesis and application of nitrogen heterocyclic azo dyes,’’ Pigment Resin Technol., 30(4), 210-228, 2001.
  • [13] J. Mikroyannidis, D. Tsagkournos, P. Balraju, G. Sharma, ‘‘Low band gap dyes based on 2-styryl-5-phenylazo-pyrrole: synthesis and application for efficient dyesensitized solar cells,’’ J. Power Sources, 196, 4152–4161, 2011.
  • [14] F. Ruyffelaere, V. Nardello, R. Schmidt, J. M. Aubry, ‘‘Photosensitizing properties and reactivity of aryl azo naphtol dyes towards singlet oxygen,’’ J Photochem Photobiol A: Chem., 183, 98–105, 2006.
  • [15] O. A. Adegoke, T. E. Adesuji, O. E. Thomas, ‘‘Novel colorimetric sensors for cyanide based on azo-hydrazone tautomeric skeletons,’’ Spectrochim Acta A Mol Biomol Spectrosc., 128, 147–152, 2014.
  • [16] P. J. Coelho, L. M. Carvalho, A. M. C. Fonseca, M. M. M. Raposo, ‘‘Photochromic properties of thienylpyrrole azo dyes in solution,’’ Tetrahedron Lett., 47, 3711–3714, 2006.
  • [17] E. Pevzner, B. Ehrenberg, ‘‘Principal component analysis of the absorption and resonance Raman spectra of the metallochromic indicator antipyrylazo III,’’ Spectrochim Acta A Mol Biomol Spectrosc., 56, 637–651, 2000.
  • [18] A. Y. Al-Ahmad, Q. M. A. Hassan, H. A. Badran, K. A. Hussain, ‘‘Investigating some linear and nonlinear optical properties of the azo dye (1-amino-2-hydroxy naphthalin sulfonic acid-[3-(4-azo)]-4-amino diphenyl sulfone),’’ Opt Laser Technol., 44(5), 1450–1455, 2012.
  • [19] M. Erfantalab, H. Khanmohammadi, ‘‘New 1, 2, 4-triazole-based azo–azomethine dye. Part III: synthesis, characterization, thermal property, spectrophotometric and computational studies,’’ Spectrochim Acta A. Mol Biomol Spectrosc., 125, 345–352, 2014.
  • [20] F. Yıldırım, A. Demirçalı, F. Karcı, A. Bayrakdar, P. T. Taşlı, H. H. Kart, ‘‘New coumarin-based disperse disazo dyes: Synthesis, spectroscopic properties and theoretical calculations,’’ J. Mol Struc., 223, 557-565, 2016.
  • [21] M. Yazdanbakhsh, H. Yousefi, M. Mamaghani, E. Moradi, M. Rassa, H. Pouramir, ‘‘Synthesis, spectral characterization and antimicrobial activity of some new azo dyes derived from 4, 6-dihydroxypyrimidine,’’ J. Mol. Liq., 169, 21–26, 2012.
  • [22] F. Karcı, N. Şener, M. Yamaç, İ. Şener, A. Demirçalı, ‘‘The synthesis, antimicrobial activity and absorption characteristics of some novel heterocyclic disazo dyes,’’ Dyes and Pigments, 80, 47–52, 2009. [23] H. Xu, X. Zeng, ‘‘Synthesis of diaryl-azo derivatives as potential antifungal agents,’’ Bioorg Med Chem Lett., 20(14), 4193–4195, 2010.
  • [24] T. I. El-Emary, S. A. A. El-Mohsen, ‘‘Multi-component one-pot synthesis and antimicrobial activities of 3-Methyl-1,4-diphenyl-7-thioxo-4, 6, 8, 9-tetrahydro-pyrazolo[5, 4-b] pyrimidino [5, 4-e] pyridine-5-one and related derivatives,’’ Molecules, 17, 14464–14483, 2012
  • [25] A. P. Acharya, R. D. Kamble, S. V. Hese, S. N. Kadam, R. N. Gacche, B. S. Dawane, ‘‘Eco-friendly synthesis of novel indeno-pyrazole derivatives and their in-vitro antimicrobial screening,’’ Org. Commun, 7(2), 68-76, 2014.
  • [26] S. G. Alegaon, K. R. Alagawadi, M. Garg, K. Dushyant, D. Vinod, ‘‘1, 3, 4-Trisubstituted pyrazole analogues as promising anti-inflammatory agents,’’ Bioorg Chem., 54, 51–59, 2014.
  • [27] P. D. Gokulan, B. Jayakar, V. Alagarsamy, V. R. Solomon, ‘‘Synthesis and Pharmacological Investigation of 5-Substituted-3-Methylsulfanyl-1H-Pyrazole-4-Carboxylic Acid Ethyl Esters as New Analgesic and anti-Inflammatory Agents,’’ Arzneimittelforschung, 62, 457–462, 2012.
  • [28] H. M. Faidallah, M. M. Al-Mohammadi, K. A. Alamry, K. A. Khan, ‘‘Synthesis and Biological Evaluation of Fluoropyrazolesulfonylurea and Thiourea Derivatives as Possible AntidiabeticAgents,’’J. Enzyme Inhib. Med. Chem., 31, 157–163, 2016.
  • [29] A.R. Ali, E.R. El-Bendary, M. A. Ghaly, I. A. Shehata, ‘‘Synthesis, in vitro anticancer evaluation and in silico studies of novel imidazo [2, 1-b] thiazole derivatives bearing pyrazole moieties,’’ Eur J Med Chem., 75, 492–500, 2014.
  • [30] M. Abdel-Aziz, GE-DA Abuo-Rahma, AA Hassan, ‘‘Synthesis of novel pyrazole derivatives and evaluation of their antidepressant and anticonvulsant activities,’’ Eur J Med Chem., 44, 3480–3487, 2009
  • [31] V. Pathak, H. K. Maurya, S. Sharma, K. K. Srivastava, A. Gupta, ‘‘Synthesis and biological evaluation of substituted 4, 6-diarylpyrimidines and 3, 5-diphenyl-4, 5-dihydro-1H-pyrazoles as anti-tubercular agents,’’ Bioorg Med Chem Lett., 24, 2892–2896, 2014
  • [32] F. Yıldırım, A. Demirçalı, P. T. Taşlı, F. Karcı, ‘‘New disazo dyes derived from aminopyrazoles: synthesis, spectroscopic properties, computational study and structural properties’’ Coloration Technology, baskıda, 2021.
  • [33] M. H. Elnagdi, M. M. M. Sallam, H. M. Fahmy, S. A. M. Ibrahim, M. A. M. Elias, ‘‘Reactions with the Arylhydrazones of α-Cyanoketones: The Structure of 2-Arylhydrazono-3-ketimino-nitriles,’’ Helv Chim.Acta., 59(2), 551-557, 1976.
  • [34] M. H. Elnagdi, G. E. H. Elgemeie, F. A. E. Abd-Ellal, ‘‘Recent Developments in the Synthesis of Pyrazole Derivative,’’ Heterocycles, 23(12), 3121- 3153, 1985.
  • [35] F. Karcı, ‘‘Synthesis of disazo dyes derived from heterocyclic components,’’ Color Technol., 121, 275-280, 2005.
  • [36] F. Karcı, A. Demirçalı, ‘‘Synthesis of disazo pyrazolo[1,5-a]pyrimidines,’’ Dyes and Pigments, 74, 288-297, 2007.
There are 35 citations in total.

Details

Primary Language Turkish
Subjects Chemical Engineering
Journal Section Makaleler
Authors

Fati Yıldırım 0000-0002-1800-1592

Project Number 2016 HZDP 036
Publication Date May 27, 2021
Published in Issue Year 2021 Volume: 16 Issue: 1

Cite

IEEE F. Yıldırım, “3-Amino-5-Hidroksi-1H-Pirazol Bazlı Bazı Yeni Disazo Boyarmaddelerinin Sentezi ve Spektroskopik Özellikleri”, Süleyman Demirel University Faculty of Arts and Science Journal of Science, vol. 16, no. 1, pp. 189–199, 2021, doi: 10.29233/sdufeffd.887728.