Aminotiyazol halkası içeren bazı yeni disazo boyar maddelerin sentezi, karakterizasyonu ve absorpsiyon özelliklerinin incelenmesi
Synthesis, characterization and investigation of absorption properties of some new disazo dyes including aminothiazol ring
Yazar: MERVE GÖKALP
Danışman: DOÇ. DR. TAHİR TİLKİ
Süleyman Demirel Üniversitesi / Fen Bilimleri Enstitüsü / Kimya Ana Bilim Dalı
Derece: Yüksek Lisans, 2017
Konu: Kimya = Chemistry

Özet:
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.

Abstract:
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).