Benzotiyazol ve pirazol halkası içeren yeni disazo boyar maddelerin sentezi, karakterizasyonu ve absorpsiyon özelliklerinin incelenmesi
Synthesis of new disazo dyes containing pyrazol and benzothiazole ring characterization and investigation of absorption properties
Yazar: GÜLŞAH CİÇEN
Danışman: DOÇ. DR. TAHİR TİLKİ ; YRD. DOÇ. DR. ÇİĞDEM KARABACAK ATAY
Süleyman Demirel Üniversitesi / Fen Bilimleri Enstitüsü / Kimya Ana Bilim Dalı
Derece: Yüksek Lisans, 2017
Konu: Kimya = Chemistry
Dizin: 2-aminobenzotiyazol = 2-aminobenzothiazole ; Spektrofotometri-atomik = Spectrophotometry-atomic

Özet:
Günümüzde hem yeni bir boyarmadde sentezlemek hem de kullanım alanlarını araştırmak büyük bir öneme sahiptir. Endüstriyel amaçlı araştırmaların yanı sıra ileri teknoloji ürünlerindede bu konuyla ilgili çalışmalar günden güne artmaktadır.
Bu tez çalışmasında ilk olarak 2-aminobenzotiyazolün diazonyum tuzu hazırlandı ve 3-aminokrotonitril kenetlemesi ile oluşan 2-hetarilhidrazon-3-ketiminobütirilonitril (3) bileşiğin hidrazinhidrat ve fenilhidrazin ile halka kapanması reaksiyonları gerçekleştirildi. Pirazol halkası içeren 5-amino-3-metil-4-hetarilazo-1H-pirazol (4a) ve 5-amino-3-metil-4-hetarilazo-1fenil-pirazol (4b) bileşiklerin yeniden diazonyum tuzları hazırlandıktan sonra 5,5dimetilsiklohekzan-1,3-dion, 2,2-dimetil-1,3-dioksan-4,6-dion, 1-metil-imidazol ve 2-metil-imidazol bileşikleriyle kenetlenme reaksiyonları sonucu disazo 2-((4-(benzo[d]tiyazol-2-il diazenil)-3-metil-1H-pirazol-5-il)diazenil)-5,5-dimetilsiklohekzan-1,3-dion (5a), 2-((4-(benzo [d]tiyazol-2-ildiazenil)-3-metil-1-fenil-1H-pirazol-5-il)diazenil)-5,5-dimetil siklo hekzan-1,3-dion (5b), 5-((1E)-(4-(benzo[d]tiyazol-2-il diazenil)-3-metil-1H-pirazol-5-il)diazenil)-2,2-dimetil-1,3-dioksan-4,6-dion (6a), 5-((1E)-(4-(benzo[d]tiyazol-2-il diazenil)-3-metil-1-fenil-1H-pirazol-5-il)diazenil)-2,2-dimetil-1,3-dioksan-4,6-dion (6b), 2-((3-metil-5-((E)-(1-metil-1H-imidazol-2-il)di azenil)-1H-pirazol- 4-il)diazenil) benzo[d]tiyazol (7a), 2-((3-metil-5-((E)-(1-metil-1H-imidazol-2-il)diazenil)-1-fenil-1H-pirazol-4-il) di azenil) benzo[d]tiyazol (7b), 2-((3-metil-5-((E)-(2-metil-1H-imidazol-5-yl)diazenil)-1H-pirazol-4-il)diazenil) benzo [d] tiyazol (8a) ve 2-((3-metil-5-((E)-(2-metil-1H-imidazol-5-il)diazenil)-1-fenil-1H-pirazol-4-il)diazenil) benzo [d] tiyazol (8b) bileşikleri elde edildi. Elde edilen bu disazo boyarmaddeler FT-IR ve 1H-NMR gibi spektral yöntemlerle karakterize edilmiştir. Görünür bölge absorpsiyon spektrumları üzerine çözücü etkisi incelenmiştir. Sonuç olarak hem başlangıç maddesi hem de kenetlenme bileşeni heterosiklik halka içeren yeni disazo boyarmaddeler sentezlenmiştir.

Abstract:
Nowadays have a great importance both to synthesize a new dyes and to investigate its application or usage areas. It's increasing interests day by day studies on usage of the high-tech in addition to investigate for industrial purposes. 
In this thesis, firstly the diazonium salt of 2-aminobenzothiazole was prepared and ring-closing reactions with hydrazine hydrate and phenylhydrazine were carried out 2-hetarylhydrazone-3-ketiminobutyrylonitrile (3) which formed with coupling reaction of 3-aminokrotonitril. Again diazonium salts of 5-amino-3-methyl-4-hetarylazo-1H-pyrazoles (4a) and 5-amino-3-methyl-4-hetarylazo-1-phenylpyrazoles (4b) containing the pyrazole ring was prepared. Subsequently, disazo dyes 2-((4-(benzo[d]thiazol-2-yldiazenyl)-3-methyl-1H-pyrazol-5-yl)diazenyl)-5,5-dimethyl cyclo hexane-1,3-dione (5a), 2-((4-(benzo[d]thiazol-2-yldiazenyl)-3-methyl-1-phenyl-1H-pyrazol-5-yl)diazenyl)-5,5-dimethyl cyclo hexane-1,3-dione (5b), 5-((1E)-(4-(benzo[d]thiazol-2-yldiazenyl)-3-methyl-1H-pyrazol-5-yl)diazenyl)-2,2-dimethyl-1,3-dioxane-4,6-dione (6a), 5-((1E)-(4-(benzo[d]thiazol-2-yldiazenyl)-3-methyl-1-phenyl-1H-pyrazol-5-yl)di azenyl)-2,2-dimethyl-1,3-dioxane-4,6-dione (6b), 2-((3-methyl-5-((E)-(1-methyl-1H-imidazol-2-yl)diazenyl)-1H-pyrazol-4-yl)diazenyl) benzo [d]thiazole (7a), 2-((3-methyl-5-((E)-(1-methyl-1H-imidazol-2-yl)diazenyl)-1-phenyl-1H-pyrazol- 4-yl)di azenyl)benzo[d]thiazole (7b), 2-((3-methyl-5-((E)-(2-methyl-1H-imidazol-5-yl)diazenyl)-1H-pyrazol-4-yl)diazenyl) benzo[d] thiazole (8a) and 2-((3-methyl-5-((E)-(2-methyl-1H-imidazol-5-yl)diazenyl)-1-phenyl-1H-pyrazol-4-yl) diazenyl)benzo[d]thiazole (8b) were obtained via coupling reaction of 5,5-dimethylcyclohexane-1,3-dione, 2,2-dimethyl-1,3-dioxane-4,6-dione, 1-methyl-1H-imidazole and 2-methyl-1H-imidazole with re-diazonium salts. These disazo dyes were characterized by spectral methods such as FT-IR and 1H-NMR. Solvent effect on visible region absorption spectra was investigated. As a result, novel disazo dyes containing both the starting material and the coupling agent heterocyclic ring were synthesized.