Department of pure and industrial chemistry, faculty of. The growing interest in heterocyclic azo dye chemistry is focused on designing. Thiophenebased azo dyes and their applications i n dyes chemistry moaz m. Textile dyes contain functional groups, such as carboxylic, amine and azo. Antibacterial activity and dyeing characteristics of some azopyazole disperse dyes using ecofriendly ultrasound energy for pet fabric. The emission of effluents from textile industries has been a major concern of the modern world, due to the great pollution that these effluents promote on the water resources. Azo dyes are organic compounds bearing the functional group r. Chapter 2 synthesis and purity assessment o f reactive d yes 28 2.
Heterocyclic definition of heterocyclic by medical. Synthesis and characterization of a new heterocyclic azo. The structure of heterocyclic compounds most chemical compounds consist of molecules. Azo dyes chudgar major reference works wiley online library.
Azoic dyes are also called as azoic or nepthol dyes. The present work describes the synthesis of novel heterocyclic azo dyes by general. Heterocyclic chemistry is the branch of organic chemistry dealing with the synthesis, properties, and applications of these heterocycles. There are many different classes of dyes in which azo dyes are certainly one of the most important classes. This chomophoric system is associated with two or more aromatic or heterocyclic rings. Azo dyes which consist of at least a conjugated azo nn chromophore 4,5 many azocompounds have been applied as chromogenic reagents for the determination of several metal ions 4,5 the use of such reagents was found to depend essentially on their uvvis spectral properties. Heterocyclic azo dyes for dye sensitized solar cells. Synthesis and application of some new disperse azo dyes derived. This divalent group is attached to sp 2 hybridized carbon atoms. Chemically related to azo dyes are azo pigments, which are insoluble in water and other solvents. Synthesis, spectroscopic characterization and pharmacological. A heterocyclic compound is an organic compound in which one or more of the carbon atoms in the backbone of the molecule has been replaced by an atom other than carbon. Some azo dyes with this property and which can revert slowly to the trans isomer in the dark are used in sunglasses and car sunroofs.
Preparation and characterization of some new azo dyes. Often, these carbons are part of aromatic systems, but this is not always the case. Fast thermal cistrans isomerization of heterocyclic azo. About half of the dyes used in industry are azo dyes. Azo compounds are considered as class of organic colorants which consist of at least a conjugated chromophore azo nn group in association with one or. Examples of secondary and tertiary aromatic amines suitable for azo dye synthesis. Since, the organic dyes that harness sunlight are generally considered as the heart of the dye sensitized solar cells dssc, the present study was carried out with the aim to design heterocyclic azo dyes that can be potentially used in dssc application. A heterocyclic compound or ring structure is a cyclic compound that has atoms of at least two different elements as members of its rings. The product was dried in the vacuum desiccator until weight. Biodegradation of azo dye compounds premier publishers. The two nitrogen atoms are bonded with each other and form nn as part of their molecular structure. The colour properties of organic dye depend on both the presence of chromophore. Pdf synthesis of heterocyclic azo dyes from quinolin8ol.
They are usually prepared through condensation of azo compounds with ketones or aldehydes. In this electrophilic aromatic substitution reaction, the aryldiazonium cation is the electrophile and the activated arene is a nucleophile. Three step synthesis of azo dye alexa harnagel, meghan reilly, ashly solis st. Combinatorial synthesis of azo dyes linfield college. Pdf the significance of heterocyclic dyestuffs has recently increased due to their deep hues and brightness. As you might expect, they all contain an azo group, nn, which links two sp 2 hybridised carbon atoms. Heterocyclic azo dyes from some of these amines offer excellent fastness. Synthesis and characterization of new azo coumarin dyes 155 the goal of this study was to use unsubstituted coumarin as a coupling component and electron donor to synthesize new azocoumrin dyes by coupling it with different diazotized aromatic amines, derived from benzene or anthraquinone. Benzene diazonium salt and 4 nitrobenzene diazonium salt were prepared by treating aniline. Request pdf on aug 15, 2015, asif mahmood and others published heterocyclic azo dyes for dye sensitized solar cells. Compounds 35 are thienylpyrrole azo dyes linked to thiazole or benzothiazole heterocycles, through positions 2 or 6, and possessing propyl or pfluorophenyl groups in the nitrogen atom of the pyrrole.
Five and sixmembered heterocycles article pdf available july 2018 with 324 reads how we measure. Thiophenebased azo dyes and their applications i n dyes. This dye was isolated as light orange yellow colour solid with 78% yield, m. Synthesis of cobaltcomplex azo dye from 2, 2benzene1, 3. Synthesis and use of fabric dyes by professor david cash. Paul, mn abstract organol brown azo dye was synthesized and altered with functional group conversions to see the effect it would have on its color.
Synthesis and antifungal activity of novel metal chelates containing. Reactions used in heterocyclic ring synthesis aldol. Dyes are used in almost every commercial product such as food, clothing, pigments and paints, etc. The term azo dyes is applied to those synthetic organic colorants that are characterized by the presence of the chromophoric azo group. The azo function is often bound to an aromatic ring, and the dye can then be broken down to an aromatic amine, arylamine. Antibacterial activity and dyeing characteristics of some. They are synthetic organic substances whose molecules contain two aromatic ring systems linked through an azo dinitrogen bridge. Synthesis, structural characterization of coii, niii. Azo dyes azo dyes are the largest and most versatile class of synthetic dyes.
Abdou egyptian petroleum research institute, nasr city, p. Heterocyclic azo dyes adaptable photochromic switches with. In most cases, including the examples below, the diazonium compound is also aromatic. In fact, about half of the dyes in industrial use today are azo dyes, which are mostly prepared from diazonium salts. Synthesis of heterocyclic azo dyes from quinolin8ol chidimma g. Heterocyclic azo dyes were synthesized by diazotation of several substituted anilines and coupling with 5n,ndialkylamino2,2. Examples of benzene, naphthalene, and heterocyclic based primary aromatic amines used in azo dye synthesis. Hydrochloric acid 1 ml was added to a flask with a suspension of 4aminobenzaldehyde or 4aminobenzoic acid 1. Generic structure for azo dyes, where ar1 and ar2 are aromatic systems. Easily share your publications and get them in front of issuus. The dyes were characterized by visible absorption spectroscopy, ir spectral studies, and 1 h and c nmr.
Their absorption maxima were observed in the range of 427631 nm, being more bathochromic than the corresponding nonhetarylazo derivatives. The azo dyes containing azo linkages have advanced applications in high technology areas like lasers 3, lcd color filters 4. However, since then, there has been a considerable growth in the volume of data reported outside of the patent literature. The concentration, form, and purity of a dye are determined largely by the use for. Synthesis of disperse dyes from pyridone and resorcinol. This can take place either chemically, through reductive cleavage, or. Patel 2 faculty of science, pacific university, udaipur 1bhavans science college, dakor, gujarat, india. We report the results of a combined experimental and theoretical study of four azodyes, derived from three different heterocyclic systems, which we used as sensitizers for tio2 dyesensitized solar cells. Design and synthesis of novel antimicrobial acyclic and. Structures of the resulting azo dyes were confirmed by ftir, uv, 1 h and c nmr, and mass spectra and elemental analyses, and their solvatochromic properties were examined. This chapter presents the preparation, properties, and applications of heterocyclic dyes. Synthesis, characterization, biological activity and. Procedure for the azo coupling of pyrrole precursors 68 with the diazonium salts 9 and 10 to afford heterocyclic azo dyes 15.
A quantum chemical study find, read and cite all the research you need on. In recent, years heterocyclic based azo dyes, have found great success due to their higher tinctorial strength, brighter dyeing and excellent light, washing and sublimation fastness, and chromophoric strength in relation to diazo dyes based uniquely on azobenzene derivatives 3. In a laboratory, they tested the white blood cells of subjects before and after drinking coffee, subjecting the ceils to two different kinds of celldamaging substances. An azo coupling is an organic reaction between a diazonium compound and another aromatic compound that produces an azo compound. Us4225489a heterocyclic azo dyes and pigments containing. The synthesis of dyes is intertwined with the birth of modern industrial organic chemistry, and some. The thiophenebased azo dyes class of azo dyes have generated considerable interest since its discovery 62 years ago.
Azo compounds are mostly used as dyes due to its various applications in the fields such as textile fibres, colouring of different materials, biomedical studies and organic synthesis 12. The aim of this study was to synthesize disperse dyes in the derivative of 2amino4chloro5formylthiazole by conventional diazotization and couplings with pyridone and resorcinol. Diazotation of 4aminobenzaldehyde and 4aminobenzoic acid. Synthesis and characterization of azo derivatives of. Azo dye compounds have many applications in industry including photosensitive, photodynamic therapy, electro photographic and photographic system applications and are predominant organic photoconductive materials. The synthesis of some novel heterocyclic azo disperse dyes derived from 5acetyl2amino4methylthiazole 1 using various nalkyl derivatives of aniline 2ae and their dyeing performance as disperse dyes have been assessed on polyester and nylon. Biodegradation of azo dye compounds irjbb biodegradation of azo dye compounds kamlesh shah department of biotechnology, p. The azo compound class accounts for 6070% of all dyes.
Azo dyes have a general structure rnnr, where r and r are aryl, alkyl, or heterocyclic groups. Purpose to synthesize some new heterocyclic disperse azo dyes and their utilization in textile printing. The first azo dye was synthesized in 1858 by griess, soon after he discovered the diazotisation reaction which is part of the synthesis. Six derivatives of heterocyclic azo dyes were synthesized by coupling diazotized aniline and 4nitroaniline with quinolin8ol, 5nitrosoquinolin8ol and 5nitroquinolin8ol respectively. Thermal reactions of 42hydroxynaphthalen1yldiazenylbenzenesulfonyl azide with cyclohexane, benzene, toluene, anisole, pxylene, mesitylene, dihydropyran, and pyridine were studied.
In summary, recently established approach of merging two or more. Typical hetero atoms include nitrogen, oxygen, and sulfur. Unsymmetrical and symmetrical bis hetarylazo dyes were prepared by diazotisationcoupling and oxidation reactions in moderate yields. A longterm aim of dyes research has been to combine the. Issuu is a digital publishing platform that makes it simple to publish magazines, catalogs, newspapers, books, and more online.
This allowed for the testing of what reactions can be used to create new variations of azo dyes. The resulting solid azo dye was washed with water, dried and recrystallized from, meoh. Aromatic hetero cyclic azo dye a as a function of substitutions r1, r2 and r3. The journal covers investigations in heterocyclic chemistry taking place in. Pdf heterocyclic azodyes as pigments for dye sensitized. Abstract the objective of this research was to use ultrasound as ecofriendly technique to enhance dyeing performance and antibacterial. Synthesis of heterocyclic azo dyes from quinolin 8. Azo dyes azo dyes are important class of organic colorants consists of at least a conjugated chromophore azo nn group and the largest and most versatile class of dyes. Synthesis, characterization and antimicrobial screening of.
The growing interest in heterocyclic azo dye chemistry is focused on. Many azo dyes, like sudan red and scarlet red, can be used as biological dyes because they are fat soluble and can be absorbed into fat cell tissues on microscope slides. The synthesis of dyes is intertwined with the birth of modern industrial organic chemistry, and some excellent treatises focus on the modern manufacture and applications of dyes. Tarek abou elmaaty, khaled elnagar, sherif hassan and hanangamal. Compounds 1 and 2 are thienylpyrrole azo dyes linked to a phenyl ring and possessing propyl or pmetoxyphenyl groups linked to the pyrrole ring. They are a commercially important family of azo compounds, i. In this way, many green azo dyes have been made by combining. Heterocyclic azodyes as pigments for dye sensitized solar cells a combined experimental and theoretical study. Azo dyes are widely used to treat textiles, leather articles, and some foods.
836 834 1139 1366 1216 1273 559 262 1371 1387 144 791 377 443 667 1518 722 1053 445 1030 1013 1592 1040 451 153 351 1180 202 470 1306 950 514