Bu tez çalışması; iki aşamada tamamlanmıştır. Birinci aşamada, 2-aminotiyazol bileşiğinin diazonyum tuzu elde edilmiştir. Elde edilen diazonyum bileşiği 3-aminokrotononitril ile kenetleme reaksiyonu gerçekleştirilerek 2-hetarilhidrazon-3-ketiminobütironitril (1) bileşiği elde edilmiştir. Elde edilen bu bileşiklerin hidrazin monohidrat ve fenil hidrazin hidrat ile halkalaşma reaksiyonu sonucu pirazol halkası içeren 5-amino-3-metil-4-hetarilazo-1H-pirazol (2) ve 5-amino-3-metil-4-hetarilazo-1fenil-pirazol (3) yapıları elde edilmiştir. Oluşan bu bileşiklerin (2,3) yeniden diazonyum tuzları hazırlanarak 4-aminobenzoik asit, 1,3-dihidroksi benzen, 1-naftol, 2-naftol ve benzen-1,3-diamin ile kenetlenmesi sonucu; 4-amino-3-((E)-(3-metil-4-((E)-tiyazol-2-il diazenil)-1H-pirazol-5-il) diazenil) benzoik asit (4a) ve 4-amino-3-((E)-(3-metil-1-fenil-4-((E)-tiazol-2-il diazenil)-1H-pirazol-5-il) diazenil) benzoik asit (5a), 4-((E)-(3-metil-4-((E)-tiazol-2-il diazenil)-1H-pirazol-5-il) diazenil) benzen-1,3-diol (4b) ve 4-((E)-(3-metil-1-fenil-4-((E)-tiyazol-2-il diazenil)-1H-pirazol-5-il) diazenil) benzen-1,3-diol (5b), 4-((E)-(3-metil-4-((E)-tiyazol-2-il diazenil)-1H-pirazol-5-il) diazenil) naftalen-1-ol (4c) ve 4-((E)-(3-metil-1-fenil-4-((E)-tiazol-2-il diazenil)-1H-pirazol-5-il) diazenil) naftalen-1-ol (5c), 1-((E)-(3-metil-4-((E)-tiazol-2-il diazenil)-1H-pirazol-5-il) diazenil) naftalen-2-ol (4d) ve 1-((E)-(3-metil-1-fenil-4-((E)-tiazol-2-il diazenil)-1H-pirazol-5-il) diazenil) naftalen-2-ol (5d), 4-((E)-(3-metil-4- ((E)-tiazol-2-il diazenil)-1H-pirazol-5-il) diazenil) benzen-1,3-diamin (4e), 4-((E)-(3-metil-1-fenil-4-((E)-tiyazol-2-il diazenil)-1H-pirazol-5-il) diazenil) benzen-1,3-diamin (5e) yeni disazo boyarmaddelerinin sentezi gerçekleştirilmiştir. İkinci aşama, sentezlenen bileşiklerin karakterizasyonunu oluşturmaktadır. Fourier Transform Infrared Spektroskopisi (FTIR), Nükleer Manyetik Rezonans Spektroskopisi (1H-NMR) gibi spektral analiz yöntemleri ile yapısal özellikleri aydınlatılarak karakterize edilmiştir. Ayrıca sentezlenen moleküllerin Görünür Bölge Spektrometresi (UV-Vis) ile 5 farklı çözücü içinde (DMSO, DMF, metanol, kloroform, asetik asit) absorpsiyon özellikleri incelenmiştir. Anahtar Kelimeler: Azo boyarmaddeler, Heterosiklik bileşikler, Aminotiyazol, Pirazol
This thesis study; was completed in two stages. In the first step, the diazonium salt of the 2-aminothiazole compound was obtained. 2-hetarylhydrazone-3-quinidinobutyronitrile (1) was obtained the realized diazonium compound was coupled with 3-aminocrotononitrile. 5-amino-3-methyl-4-hetarylazo-1H-pyrazole (2) and 5-amino-3-methyl-4-hetarylazo-1-phenyl-pyrazole (3) which containing pyrazol ring were obtained with the resulting cyclization reaction with hydrazine monohydrate and phenyl hydrazine hydrate. The resulting diazonium salts of these compounds (2,3) were prepared and coupled with 4-aminobenzoic acid, 1,3-dihydroxy benzene, 1-naphthol, 2-naphthol and benzene-1,3-diamine; 4-((E)-(3-metil-1-fenil-4-((E)-tiyazol-2-il diazenil)-1H-pirazol-5-il) diazenil) benzen-1,3-diol (4a) and 4-amino-3-((E)-(3-methyl-1-phenyl-4-((E)-thiazol-2-yldiazenyl)-1H-pyrazol-5-yl)diazenyl)benzoic acid (5a), 4-((E)-(3-metil-1-fenil-4-((E)-tiyazol-2-il diazenil)-1H-pirazol-5-il) diazenil) benzen-1,3-diol (4b) and 4-((E)-(3-methyl-1-phenyl-4-((E)-thiazol-2-yldiazenyl)-1H-pyrazol-5-yl)diazenyl)benzene-1,3-diol (5b), 4-((E)-(3-methyl-4-((E)-thiazol-2-yldiazenyl)-1H-pyrazol-5-yl)diazenyl)naphthalen-1-ol (4c) and 4-((E)-(3-methyl-1-phenyl-4-((E)-thiazol-2-yldiazenyl)-1H-pyrazol-5-yl) diazenyl) naphthalen-1-ol (5c), 1-((E)-(3-methyl-4-((E)-thiazol-2-yldiazenyl)-1H-pyrazol-5-yl)diazenyl)naphthalen-2-ol (4d) and 1-((E)-(3-methyl-1-phenyl-4-((E)-thiazol-2-yldiazenyl)-1H-pyrazol-5-yl)diazenyl)naphthalen-2-ol (5d), 4-((E)-(3-methyl-4-((E)-thiazol-2-yldiazenyl)-1H-pyrazol-5-yl)diazenyl)benzene-1,3-diamine (4e) and 4-((E)-(3-methyl-1-phenyl-4-((E)-thiazol-2-yldiazenyl)-1H-pyrazol-5-yl) diazenyl) benzene-1,3-diamine (5e) synthesis of new disazo dyes was carried out. The second step is the characterization of the synthesized compounds. It was characterized spectral analysis methods which solved structural features like Fourier Transform Infrared Spectroscopy (FTIR) and Nuclear Magnetic Resonance Spectroscopy (1H-NMR). In addition, the absorption characteristics of the synthesized molecules were examined in 5 different solvents (DMSO, DMF, methanol, chloroform, acetic acid) by Visible Region Spectrometry (UV-Vis). Keywords: Azo dyes, Heterocyclic compounds, Aminothiazole, Pyrazole
Tez (Yüksek Lisans) - Süleyman Demirel Üniversitesi, Fen Bilimleri Enstitüsü, Kimya Anabilim Dalı, 2017.
Kaynakça var.
Bu tez çalışması; iki aşamada tamamlanmıştır. Birinci aşamada, 2-aminotiyazol bileşiğinin diazonyum tuzu elde edilmiştir. Elde edilen diazonyum bileşiği 3-aminokrotononitril ile kenetleme reaksiyonu gerçekleştirilerek 2-hetarilhidrazon-3-ketiminobütironitril (1) bileşiği elde edilmiştir. Elde edilen bu bileşiklerin hidrazin monohidrat ve fenil hidrazin hidrat ile halkalaşma reaksiyonu sonucu pirazol halkası içeren 5-amino-3-metil-4-hetarilazo-1H-pirazol (2) ve 5-amino-3-metil-4-hetarilazo-1fenil-pirazol (3) yapıları elde edilmiştir. Oluşan bu bileşiklerin (2,3) yeniden diazonyum tuzları hazırlanarak 4-aminobenzoik asit, 1,3-dihidroksi benzen, 1-naftol, 2-naftol ve benzen-1,3-diamin ile kenetlenmesi sonucu; 4-amino-3-((E)-(3-metil-4-((E)-tiyazol-2-il diazenil)-1H-pirazol-5-il) diazenil) benzoik asit (4a) ve 4-amino-3-((E)-(3-metil-1-fenil-4-((E)-tiazol-2-il diazenil)-1H-pirazol-5-il) diazenil) benzoik asit (5a), 4-((E)-(3-metil-4-((E)-tiazol-2-il diazenil)-1H-pirazol-5-il) diazenil) benzen-1,3-diol (4b) ve 4-((E)-(3-metil-1-fenil-4-((E)-tiyazol-2-il diazenil)-1H-pirazol-5-il) diazenil) benzen-1,3-diol (5b), 4-((E)-(3-metil-4-((E)-tiyazol-2-il diazenil)-1H-pirazol-5-il) diazenil) naftalen-1-ol (4c) ve 4-((E)-(3-metil-1-fenil-4-((E)-tiazol-2-il diazenil)-1H-pirazol-5-il) diazenil) naftalen-1-ol (5c), 1-((E)-(3-metil-4-((E)-tiazol-2-il diazenil)-1H-pirazol-5-il) diazenil) naftalen-2-ol (4d) ve 1-((E)-(3-metil-1-fenil-4-((E)-tiazol-2-il diazenil)-1H-pirazol-5-il) diazenil) naftalen-2-ol (5d), 4-((E)-(3-metil-4- ((E)-tiazol-2-il diazenil)-1H-pirazol-5-il) diazenil) benzen-1,3-diamin (4e), 4-((E)-(3-metil-1-fenil-4-((E)-tiyazol-2-il diazenil)-1H-pirazol-5-il) diazenil) benzen-1,3-diamin (5e) yeni disazo boyarmaddelerinin sentezi gerçekleştirilmiştir. İkinci aşama, sentezlenen bileşiklerin karakterizasyonunu oluşturmaktadır. Fourier Transform Infrared Spektroskopisi (FTIR), Nükleer Manyetik Rezonans Spektroskopisi (1H-NMR) gibi spektral analiz yöntemleri ile yapısal özellikleri aydınlatılarak karakterize edilmiştir. Ayrıca sentezlenen moleküllerin Görünür Bölge Spektrometresi (UV-Vis) ile 5 farklı çözücü içinde (DMSO, DMF, metanol, kloroform, asetik asit) absorpsiyon özellikleri incelenmiştir. Anahtar Kelimeler: Azo boyarmaddeler, Heterosiklik bileşikler, Aminotiyazol, Pirazol
This thesis study; was completed in two stages. In the first step, the diazonium salt of the 2-aminothiazole compound was obtained. 2-hetarylhydrazone-3-quinidinobutyronitrile (1) was obtained the realized diazonium compound was coupled with 3-aminocrotononitrile. 5-amino-3-methyl-4-hetarylazo-1H-pyrazole (2) and 5-amino-3-methyl-4-hetarylazo-1-phenyl-pyrazole (3) which containing pyrazol ring were obtained with the resulting cyclization reaction with hydrazine monohydrate and phenyl hydrazine hydrate. The resulting diazonium salts of these compounds (2,3) were prepared and coupled with 4-aminobenzoic acid, 1,3-dihydroxy benzene, 1-naphthol, 2-naphthol and benzene-1,3-diamine; 4-((E)-(3-metil-1-fenil-4-((E)-tiyazol-2-il diazenil)-1H-pirazol-5-il) diazenil) benzen-1,3-diol (4a) and 4-amino-3-((E)-(3-methyl-1-phenyl-4-((E)-thiazol-2-yldiazenyl)-1H-pyrazol-5-yl)diazenyl)benzoic acid (5a), 4-((E)-(3-metil-1-fenil-4-((E)-tiyazol-2-il diazenil)-1H-pirazol-5-il) diazenil) benzen-1,3-diol (4b) and 4-((E)-(3-methyl-1-phenyl-4-((E)-thiazol-2-yldiazenyl)-1H-pyrazol-5-yl)diazenyl)benzene-1,3-diol (5b), 4-((E)-(3-methyl-4-((E)-thiazol-2-yldiazenyl)-1H-pyrazol-5-yl)diazenyl)naphthalen-1-ol (4c) and 4-((E)-(3-methyl-1-phenyl-4-((E)-thiazol-2-yldiazenyl)-1H-pyrazol-5-yl) diazenyl) naphthalen-1-ol (5c), 1-((E)-(3-methyl-4-((E)-thiazol-2-yldiazenyl)-1H-pyrazol-5-yl)diazenyl)naphthalen-2-ol (4d) and 1-((E)-(3-methyl-1-phenyl-4-((E)-thiazol-2-yldiazenyl)-1H-pyrazol-5-yl)diazenyl)naphthalen-2-ol (5d), 4-((E)-(3-methyl-4-((E)-thiazol-2-yldiazenyl)-1H-pyrazol-5-yl)diazenyl)benzene-1,3-diamine (4e) and 4-((E)-(3-methyl-1-phenyl-4-((E)-thiazol-2-yldiazenyl)-1H-pyrazol-5-yl) diazenyl) benzene-1,3-diamine (5e) synthesis of new disazo dyes was carried out. The second step is the characterization of the synthesized compounds. It was characterized spectral analysis methods which solved structural features like Fourier Transform Infrared Spectroscopy (FTIR) and Nuclear Magnetic Resonance Spectroscopy (1H-NMR). In addition, the absorption characteristics of the synthesized molecules were examined in 5 different solvents (DMSO, DMF, methanol, chloroform, acetic acid) by Visible Region Spectrometry (UV-Vis). Keywords: Azo dyes, Heterocyclic compounds, Aminothiazole, Pyrazole