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PİRAZOL BAZLI DİSAZO BOYARMADDELERİN SENTEZİ, KARAKTERİZASYONU VE ABSORPSİYON ÖZELLİKLERİNİN İNCELENMESİ

Yıl 2017, Cilt 19, Sayı 55, 194 - 202, 01.01.2017
https://doi.org/10.21205/deufmd.2017195515

Öz

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

Kaynakça

  • [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

Yıl 2017, Cilt 19, Sayı 55, 194 - 202, 01.01.2017
https://doi.org/10.21205/deufmd.2017195515

Öz

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

Kaynakça

  • [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.

Ayrıntılar

Birincil Dil Türkçe
Konular Temel Bilimler
Diğer ID JA84CM97RZ
Bölüm Araştırma Makalesi
Yazarlar

Çiğdem KARABACAK ATAY (Sorumlu Yazar)


Merve GÖKALP Bu kişi benim


Tahir TİLKİ Bu kişi benim

Yayımlanma Tarihi 1 Ocak 2017
Yayınlandığı Sayı Yıl 2017, Cilt 19, Sayı 55

Kaynak Göster

Bibtex @araştırma makalesi { deumffmd491800, journal = {Dokuz Eylül Üniversitesi Mühendislik Fakültesi Fen ve Mühendislik Dergisi}, issn = {1302-9304}, eissn = {2547-958X}, address = {DOKUZ EYLÜL ÜNİVERSİTESİ MÜHENDİSLİK FAKÜLTESİ TINAZTEPE YERLEŞKESİ 35390 BUCA/İZMİR}, publisher = {Dokuz Eylül Üniversitesi}, year = {2017}, volume = {19}, number = {55}, pages = {194 - 202}, doi = {10.21205/deufmd.2017195515}, title = {PİRAZOL BAZLI DİSAZO BOYARMADDELERİN SENTEZİ, KARAKTERİZASYONU VE ABSORPSİYON ÖZELLİKLERİNİN İNCELENMESİ}, key = {cite}, author = {Karabacak Atay, Çiğdem and Gökalp, Merve and Tilki, Tahir} }
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 . DOI: 10.21205/deufmd.2017195515
MLA Karabacak Atay, Ç. , Gökalp, M. , Tilki, T. "PİRAZOL BAZLI DİSAZO BOYARMADDELERİN SENTEZİ, KARAKTERİZASYONU VE ABSORPSİYON ÖZELLİKLERİNİN İNCELENMESİ" . Dokuz Eylül Üniversitesi Mühendislik Fakültesi Fen ve Mühendislik Dergisi 19 (2017 ): 194-202 <https://dergipark.org.tr/tr/pub/deumffmd/issue/40775/491800>
Chicago Karabacak Atay, Ç. , Gökalp, M. , Tilki, T. "PİRAZOL BAZLI DİSAZO BOYARMADDELERİN SENTEZİ, KARAKTERİZASYONU VE ABSORPSİYON ÖZELLİKLERİNİN İNCELENMESİ". Dokuz Eylül Üniversitesi Mühendislik Fakültesi Fen ve Mühendislik Dergisi 19 (2017 ): 194-202
RIS TY - JOUR T1 - PİRAZOL BAZLI DİSAZO BOYARMADDELERİN SENTEZİ, KARAKTERİZASYONU VE ABSORPSİYON ÖZELLİKLERİNİN İNCELENMESİ AU - Çiğdem Karabacak Atay , Merve Gökalp , Tahir Tilki Y1 - 2017 PY - 2017 N1 - doi: 10.21205/deufmd.2017195515 DO - 10.21205/deufmd.2017195515 T2 - Dokuz Eylül Üniversitesi Mühendislik Fakültesi Fen ve Mühendislik Dergisi JF - Journal JO - JOR SP - 194 EP - 202 VL - 19 IS - 55 SN - 1302-9304-2547-958X M3 - doi: 10.21205/deufmd.2017195515 UR - https://doi.org/10.21205/deufmd.2017195515 Y2 - 2022 ER -
EndNote %0 Dokuz Eylül Üniversitesi Mühendislik Fakültesi Fen ve Mühendislik Dergisi PİRAZOL BAZLI DİSAZO BOYARMADDELERİN SENTEZİ, KARAKTERİZASYONU VE ABSORPSİYON ÖZELLİKLERİNİN İNCELENMESİ %A Çiğdem Karabacak Atay , Merve Gökalp , Tahir Tilki %T PİRAZOL BAZLI DİSAZO BOYARMADDELERİN SENTEZİ, KARAKTERİZASYONU VE ABSORPSİYON ÖZELLİKLERİNİN İNCELENMESİ %D 2017 %J Dokuz Eylül Üniversitesi Mühendislik Fakültesi Fen ve Mühendislik Dergisi %P 1302-9304-2547-958X %V 19 %N 55 %R doi: 10.21205/deufmd.2017195515 %U 10.21205/deufmd.2017195515
ISNAD Karabacak Atay, Çiğdem , Gökalp, Merve , Tilki, Tahir . "PİRAZOL BAZLI DİSAZO BOYARMADDELERİN SENTEZİ, KARAKTERİZASYONU VE ABSORPSİYON ÖZELLİKLERİNİN İNCELENMESİ". Dokuz Eylül Üniversitesi Mühendislik Fakültesi Fen ve Mühendislik Dergisi 19 / 55 (Ocak 2017): 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. Dokuz Eylül Üniversitesi Mühendislik Fakültesi Fen ve Mühendislik Dergisi. 2017; 19(55): 194-202.
Vancouver Karabacak Atay Ç. , Gökalp M. , Tilki T. PİRAZOL BAZLI DİSAZO BOYARMADDELERİN SENTEZİ, KARAKTERİZASYONU VE ABSORPSİYON ÖZELLİKLERİNİN İNCELENMESİ. Dokuz Eylül Üniversitesi Mühendislik Fakültesi Fen ve Mühendislik Dergisi. 2017; 19(55): 194-202.
IEEE Ç. Karabacak Atay , M. Gökalp ve T. Tilki , "PİRAZOL BAZLI DİSAZO BOYARMADDELERİN SENTEZİ, KARAKTERİZASYONU VE ABSORPSİYON ÖZELLİKLERİNİN İNCELENMESİ", Dokuz Eylül Üniversitesi Mühendislik Fakültesi Fen ve Mühendislik Dergisi, c. 19, sayı. 55, ss. 194-202, Oca. 2017, doi:10.21205/deufmd.2017195515