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PİRAZOL BAZLI DİSAZO BOYARMADDELERİN SENTEZİ, KARAKTERİZASYONU VE ABSORPSİYON ÖZELLİKLERİNİN İNCELENMESİ

Year 2017, , 194 - 202, 01.01.2017
https://doi.org/10.21205/deufmd.2017195515

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

  • [1] Mikroyannidis, J.A., Tsagkournos, D.V., Balraju, P., Sharma, G.D. 2011. Low band gap dyes based on 2-styryl-5-phenylazo-pyrrole: Synthesis and application for efficient dye-sensitized solar cells: Journal of Power Sources, Cilt.196, s.4152–4161.
  • [2] Al-Ahmad, A.Y., Hassan, Q.M.A., Badran, H.A., Hussain, K.A. 2012. 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): Optics & Laser Technology, Cilt. 44, s.1450–1455.
  • [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.

Synthesis, Characterization and Investigation of Absorption Propertiesof Pyrazole Based Disazo Dyes

Year 2017, , 194 - 202, 01.01.2017
https://doi.org/10.21205/deufmd.2017195515

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

  • [1] Mikroyannidis, J.A., Tsagkournos, D.V., Balraju, P., Sharma, G.D. 2011. Low band gap dyes based on 2-styryl-5-phenylazo-pyrrole: Synthesis and application for efficient dye-sensitized solar cells: Journal of Power Sources, Cilt.196, s.4152–4161.
  • [2] Al-Ahmad, A.Y., Hassan, Q.M.A., Badran, H.A., Hussain, K.A. 2012. 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): Optics & Laser Technology, Cilt. 44, s.1450–1455.
  • [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.
There are 15 citations in total.

Details

Primary Language Turkish
Other ID JA84CM97RZ
Journal Section Research Article
Authors

Çiğdem Karabacak Atay

Merve Gökalp This is me

Tahir Tilki This is me

Publication Date January 1, 2017
Published in Issue Year 2017

Cite

APA Karabacak Atay, Ç., Gökalp, M., & Tilki, T. (2017). PİRAZOL BAZLI DİSAZO BOYARMADDELERİN SENTEZİ, KARAKTERİZASYONU VE ABSORPSİYON ÖZELLİKLERİNİN İNCELENMESİ. Dokuz Eylül Üniversitesi Mühendislik Fakültesi Fen Ve Mühendislik Dergisi, 19(55), 194-202. https://doi.org/10.21205/deufmd.2017195515
AMA Karabacak Atay Ç, Gökalp M, Tilki T. PİRAZOL BAZLI DİSAZO BOYARMADDELERİN SENTEZİ, KARAKTERİZASYONU VE ABSORPSİYON ÖZELLİKLERİNİN İNCELENMESİ. DEUFMD. January 2017;19(55):194-202. doi:10.21205/deufmd.2017195515
Chicago Karabacak Atay, Çiğdem, Merve Gökalp, and Tahir Tilki. “PİRAZOL BAZLI DİSAZO BOYARMADDELERİN SENTEZİ, KARAKTERİZASYONU VE ABSORPSİYON ÖZELLİKLERİNİN İNCELENMESİ”. Dokuz Eylül Üniversitesi Mühendislik Fakültesi Fen Ve Mühendislik Dergisi 19, no. 55 (January 2017): 194-202. https://doi.org/10.21205/deufmd.2017195515.
EndNote Karabacak Atay Ç, Gökalp M, Tilki T (January 1, 2017) PİRAZOL BAZLI DİSAZO BOYARMADDELERİN SENTEZİ, KARAKTERİZASYONU VE ABSORPSİYON ÖZELLİKLERİNİN İNCELENMESİ. Dokuz Eylül Üniversitesi Mühendislik Fakültesi Fen ve Mühendislik Dergisi 19 55 194–202.
IEEE Ç. Karabacak Atay, M. Gökalp, and T. Tilki, “PİRAZOL BAZLI DİSAZO BOYARMADDELERİN SENTEZİ, KARAKTERİZASYONU VE ABSORPSİYON ÖZELLİKLERİNİN İNCELENMESİ”, DEUFMD, vol. 19, no. 55, pp. 194–202, 2017, doi: 10.21205/deufmd.2017195515.
ISNAD Karabacak Atay, Çiğdem et al. “PİRAZOL BAZLI DİSAZO BOYARMADDELERİN SENTEZİ, KARAKTERİZASYONU VE ABSORPSİYON ÖZELLİKLERİNİN İNCELENMESİ”. Dokuz Eylül Üniversitesi Mühendislik Fakültesi Fen ve Mühendislik Dergisi 19/55 (January 2017), 194-202. https://doi.org/10.21205/deufmd.2017195515.
JAMA Karabacak Atay Ç, Gökalp M, Tilki T. PİRAZOL BAZLI DİSAZO BOYARMADDELERİN SENTEZİ, KARAKTERİZASYONU VE ABSORPSİYON ÖZELLİKLERİNİN İNCELENMESİ. DEUFMD. 2017;19:194–202.
MLA Karabacak Atay, Çiğdem et al. “PİRAZOL BAZLI DİSAZO BOYARMADDELERİN SENTEZİ, KARAKTERİZASYONU VE ABSORPSİYON ÖZELLİKLERİNİN İNCELENMESİ”. Dokuz Eylül Üniversitesi Mühendislik Fakültesi Fen Ve Mühendislik Dergisi, vol. 19, no. 55, 2017, pp. 194-02, doi:10.21205/deufmd.2017195515.
Vancouver Karabacak Atay Ç, Gökalp M, Tilki T. PİRAZOL BAZLI DİSAZO BOYARMADDELERİN SENTEZİ, KARAKTERİZASYONU VE ABSORPSİYON ÖZELLİKLERİNİN İNCELENMESİ. DEUFMD. 2017;19(55):194-202.

Dokuz Eylül Üniversitesi, Mühendislik Fakültesi Dekanlığı Tınaztepe Yerleşkesi, Adatepe Mah. Doğuş Cad. No: 207-I / 35390 Buca-İZMİR.