Preparation of Some Azo Compound Derived From Schiffe Bases Compounds and Study their Photo Chemical Properties

Abstract

The research work in this thesis composed of two parts, which are: Part One: Organic Synthesis The synthesis of Schiff and azo- Schiff bases which are shown in schemes (1,2,3,4,5,6) includes the following steps and reactions: 1. Bis azo- Bis aromatic amine [M1] has been prepared by irradiating one millimole of terephthalaldehyde with two millimoles of 1,6 diaminopyridine. Numbers of tertra-Schiff bases [M2 –M10] were prepared by condensation of one millimole of the compound [M1] with two millimoles of substituted aromatic aldehydes using fusion and reflux (in absolute ethanol) methods. 2. Numbers of azo-Salicylaldehyde[M11 – M15] were prepared from the reaction of the diazonium salts derived from (Aniline, 4- Toluidine, 4- Nitroaniline) with salicyladehyde at (0-5°C). 3. Numbers of bis azo-bis Schiff bases [M16 – M20] were prepared by reaction the compound [M1] with the compounds [M11 – M15] in microwave oven . 4. Bisazo- bis Schiff bases [M21 – M24] were prepared through coupling reaction of the compounds[M11 – M15]with diazonium salt of sulphanilic acid. 5. Tetra azo-bis Schiff bases[M25 – M28] were prepared from the condensation reaction of equimillimoles of benzidine and compounds[M11 – M15] in absolute ethanol. 6. Bis azo – Schiff bases of Congo red dye [M29 – M35]were prepared by irradiating unimillimole of Congo red with two millimoles of aromatic aldehydes in Dimethylformamide (DMF) in microwave , in the presence and absence of a few drops of acetic acid. 7. Azo- amine- ketone compounds [M36 – M38] were prepared from the coupling reaction of the compounds [M11 – M15] with diazonium salt of 4-Aminoacetophenone. 8. Bis azo–bis Schiff bases-ketones [M39 – M41]were prepared from the condensation reaction of two millimoles of the compounds [M36 – M38]with unimillimole of terphthaldehyde in absolute ethanol. 9. Bis azo–bisSchiff bases of 1,5-diaminoanthraquinone dye [M42 – M46] were prepared by fusing two millimoles of the compounds [M11 – M15] with unimillimole of 1,5-diaminoanthraquinone dye. The prepared compounds were identified using the available spectral methods (UV-visible, IR, NMR, C. H. N.).The results indicated the validity of the proposed structures. Part Two: The photochemical studies of the prepared compounds In this part, thermal performance and photo stabilities of the compounds prepared in this study were tested by subjecting them as solutions in dimethyl sulfoxide to direct sunlight. The results of exposure showed an increase in temperature of azo- Schiff bases compared to the solvent and the azo- amine derived from them ranged between (1-6) and (1- 10) degrees through the exposing system manufactured in this study. The photostability studies towards the direct sun light proved very high stability of the prepared tetra - Schiff bases and reasonable stability of the di- Schiff-diazo compound ,in general ,compared with their precursors of azo – amin , azo aldehyed ,and 1,5 – diamino anthraquinone .Only the Schiff bases derved from Congo red dye revealed limited stability .The study showed that the increase in the azo groups in Schiff base – azo compound had an adverse effect on their photostabbility