PİRAZOL BAZLI DİSAZO BOYARMADDELERİN SENTEZİ, KARAKTERİZASYONU VE ABSORPSİYON ÖZELLİKLERİNİN İNCELENMESİ
Abstract
Çalışmamızda, o-, m-, p-NO2 sübstitüe anilin türevleri diazolanmış ve etilsiyanoasetat ile kenetlenerek etil 2-siyano-2-(2-(nitrofenil) hidrazon)asetat bileşikleri elde edilmiştir. Elde edilen etil 2-siyano-2-(2(nitrofenil) hidrazon)asetat bileşikleri, hidrazinhidrat ile reaksiyona sokularak bir seri 5-amino-4-((nitrofenil) diazenil)-1H-pirazol-3-ol türevleri sentezlenmiştir. Sentezlenen 5-amino-4-((nitrofenil) diazenil)1H-pirazol-3-ol bileşiklerinin 3,5-dimetil-1H-pirazol ve 3,5-dimetil-1-fenil1H-pirazol bileşikleri ile kenetlenme reaksiyonu sonucunda ise sırasıyla 5((3,5-dimetil-1H-pirazol-4-il)diazenil)-4-((nitrofenil) diazenil)-1H-pirazol3-ol ve 5-((3,5-dimetil-1-fenil-1H-pirazol-4-il)diazenil)-4-((nitrofenil) diazenil)-1H-pirazol-3-ol disazo boyarmaddeleri elde edilmiştir. Elde edilen bu disazo boyarmaddeleri FT- IR (Fourier-Transform Infrared Spektroskopisi), Spektroskopisi) gibi spektral yöntemlerle karakterize edilmiş ve görünür bölge absorpsiyon spektrumları üzerine değişik çözücü etkisi incelenmiştir. Böylece hem diazo hem de kenetlenme bileşeni heterosiklik olan yeni disazo boyarmaddeler sentezlenerek daha batokromik renklerin elde edilmesi amaçlanmıştır
References
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Abstract
diazotised and coupled with ethylcyanoacetate to give ethyl 2-cyano-2-(2- (nitrophenyl) hydrazono)acetate. Ethyl 2-cyano-2-(2-(nitrophenyl) hydrazono)acetate were then reacted with hydrazinehydrate to give 5- amino-4-(nitrophenyl) diazenyl)-1H-pyrazol-3-ol derivatives. As a result of the coupling reactions of synthesized 5-amino-4-(nitrophenyl) diazenyl)-1H-pyrazol-3-ol compounds with 3,5-dimethyl-1H-pyrazole and 3,5-dimethyl-1-phenyl-1H-pyrazole, respectively, 5-((3,5-dimethyl-1H- pyrazol-4-yl)diazenyl)-4-(nitrophenyl) diazenyl)-1H-pyrazol-3-ol and 5- ((3,5-dimethyl-1-phenyl-1H-pyrazol-4-yl) diazenyl)-1H-pyrazol-3-ol disazo dyes were obtained. The synthesized disazo dyes were characterized by spectral methods such as FT-IR and 1H- NMR. The effect of varying solvent, upon the absorption ability of dyes was
References
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- [3] Pevzner, E., Ehrenberg, B. 2000. Principal component analysis of the absorption and resonance Raman spectra of the metallochromic indicator antipyrylazo III: Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, Cilt. 556, s.637–651.
- [4] Adegoke, O.A., Adesuji, T.E., Thomas, O.E. 2014. Novel colorimetric sensors for cyanide based on azo-hydrazone tautomeric skeletons: Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, Cilt.128, s.147–152.
- [5] Coelho, P.J., Carvalho, L.M., Fonseca, A.M.C., Raposo, M.M.M. 2006. Photochromic properties of thienylpyrrole azo dyes in solution: Tetrahedron Letters, Cilt. 47, s.3711–3714.
- [6] Ruyffelaere, F., Nardello, V., Schmidt, R., Aubry, J.M. 2006. Photosensitizing properties and reactivity of aryl azo naphtol dyes towards singlet oxygen: Journal of Photochemistry and Photobiology A: Chemistry, Cilt.183, s.98–105.
- [7] Ucun, F., Sağlam, A., Kara, I., Karcı, F. 2008. Investigation of ground state tautomeric form of a heterocyclic disazo dye derived from barbituric acid by ab initio Hartree–Fock and density functional theory calculations: Journal of Molecular Structure: THEOCHEM, Cilt.868, s.94–100.
- [8] Karabacak Atay, Ç., Kara, Y., Gökalp, M., Kara, İ., Tilki, T., Karcı, F. 2016. Disazo dyes containing pyrazole and indole moieties: Synthesis, characterization, absorption characteristics, theoretical calculations, structural and electronic properties: Journal of Molecular Liquids, Cilt.215, s.647-655.
- [9] Karcı, F., Demircalı, A., Karcı, F., Kara, I., Ucun, F. 2009. The synthesis, spectroscopic properties and theoretical calculation of some novel disperse disazo dyes derived from 3- amino-5-hydroxy-1-phenyl pyrazole: Journal of Molecular Structure, Cilt.935, s.19–26.
- [10] Yousefi, H., Yahyazadeh, A., Moradi Rufchahi, E.O., Rassa, M. 2013. Synthesis, spectral properties, biological activity and application of new 4- (benzyloxy)phenol derived azo dyes for polyester fiber dyeing: Journal of Molecular Liquids, Cilt.180, s.51–58.
- [11] Karabacak, Ç., Tilki, T., Tuncer Özden, B., Cengiz, M. 2015. Antimicrobial Pyrazole Dyes: Synthesis, Characterization and Absorption Characteristics: Research on Chemical Intermediates, Cilt.41(4), s.1985- 1999.
- [12] Karcı, F. 2005. Synthesis of disazo dyes derived from heterocyclic components: Coloration Technology, Cilt.121, s.275-282.
- [13] Sabnis, R.W., Rangnekar, D.W. 1990. Synthesis of 2-azo-3-cyano5-carbethoxy thiophene derivatives and their application on polyester fibres: Journal of Chemical Technology & Biotechnology, Cilt.47, s.39-46.
- [14] Mohammadi, A., Khalili, B., Tahavor, M. 2015. Novel push– pull heterocyclic azo disperse dyes containing piperazine moiety: Synthesis, spectral properties, antioxidant activity and dyeing performance on polyester fibers: Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, Cilt.150, s.799–805.
- [15] Rizk, H.F., Ibrahim, S.A., ElBorai, M.A. 2015. Synthesis, fastness properties, color assessment and antimicrobial activity of some azo reactive dyes having pyrazole moiety: Dyes and Pigments, 112, s.86-92.
Details
| Primary Language | Turkish |
|---|---|
| Other ID | JA84CM97RZ |
| Journal Section | Research Article |
| Authors | |
| Publication Date | January 1, 2017 |
| Published in Issue | Year 2017 Volume: 19 Issue: 55 |
Cite
Dokuz Eylül Üniversitesi, Mühendislik Fakültesi Dekanlığı Tınaztepe Yerleşkesi, Adatepe Mah. Doğuş Cad. No: 207-I / 35390 Buca-İZMİR.