| Azocompounds are important industrial products that have been widely used in many high technology fields in recent years due to their excellent optical performances such as photochromism, optical anisotropy and nonlinear optical properties. Hydroxyquinoline azobenzene compounds, which can form stable complexes with many metal ions, are also an important kind of anion recognition receptors and therefore have been used comprehensively in anion recognition. There are many methods to synthesize azocompounds and among those the better one is solid phase synthesis. The method of solid phase synthesis, which plays a more important role in the fields of organic synthesis, materials preparation, medicinal chemistry and fine chemicals, has a series of advantages including simple process, high yield, high reaction selectivity, easy to control reaction condition, low energy consumption, no solvents and less pollution and so on.In this thesis two series of 8-hydroxyquinoline and 2-naphthol, a total of seven azocompounds, were synthesized by solid phase synthesis. The target compounds were confirmed by 1HNMR, IR, UV-Vis and melting point. The reaction conditions including reactant molar ratio, and the amount of sodium nitrite were investigated. The results of test showed that the best reaction conditions was:reaction time 20 min, the molar ratio of amidogen(-NH2),8-hydroxyquinoline to sodium nitrite 1:1.2:1.04. Under the optimum conditions the yields of title compounds were 48.1%-91%.The results of the investigation of 8-hydroxyquinoline azocompounds in different solvents using UV-Vis absorption spectrums indicated that there exist azo and hydrazone isomers. The tautomeric equilibria of azo and hydrazone were affected by solvents, substituents, and intramolecular hydrogen bond in 8-hydroxyquinoline. Moreover, the red-shift of absorption peaks of 8-hydroxyquinoline azocompounds will take place with an increase in the polarity of solvents and the electron-attractive ability of the substituents. |
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