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Synthesis and Spectral Properties of Carbazol-containing Acylhydrazone Schiff Bases

Author: TanHui
Tutor: GuoDongCai
School: Hunan University
Course: Chemical Engineering
Keywords: Schiff base Hydrazone Synthesis Fluorescence Carbazole Azo
CLC: O641.4
Type: Master's thesis
Year: 2009
Downloads: 298
Quote: 1
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Abstract


Hydrazone is a class containing special Schiff base of the amide bond (-CONH-). Because of its strong coordination ability, the diverse ligands form a wide range of medical and biological activity, and nonlinear optical properties and other characteristics, caused interest in the study of science and technology workers at home and abroad, the results of the analysis, catalytic and optoelectronic materials and other aspects have been widely used. This article was designed and synthesized 22 new Carbazole-containing acylhydrazone Schiff base, its research work is divided into the following three parts: (1) Synthesis of 4 - (N-carbazolyl) benzoyl hydrazine and the two hydrazide N-carbazolyl Acethydrazide, then its respectively associated with different the substituted benzaldehyde Preparation 18 containing carbazolyl acylhydrazone Schiff base, which has 14 not been reported in the literature. By 1H NMR spectroscopy, mass spectrometry, infrared spectroscopy and elemental analysis methods were used to characterize the structure of the Schiff base and its intermediates. Explore the synthesis of 4 - (N-carbazole methyl) benzoic acid and containing carbazolyl acylhydrazone Schiff base optimal reaction conditions. The experiments show that: ethanol - glacial acetic acid solvent system synthesis of Schiff base, mild reaction conditions, the product is easy purification; ethanol and glacial acetic acid volume ratio of 10:0.5 when most of the Schiff base yield can be achieved most good (85%). (2) on the basis of the first part of the work, 18 acylhydrazone synthesized Schiff base ultraviolet spectroscopy, fluorescence and fluorescence quantum yield. The results show that: the electron donating groups Schiff base maximum UV absorption peak wavelength occurs in varying degrees of redshift electron withdrawing group has little influence. Electron-withdrawing groups and for the introduction of the electronic group maximum fluorescence emission wavelength redshift of the Schiff base. Introduction of electron donating groups (-CH3,-OCH3), make Schiff bases fluorescence intensity increases, the fluorescence quantum efficiency was significantly improved; 4 - and 2 - position electron donating groups (-OH) the introduction of the Schiff base maximum emission wavelength occurred significantly redshift; 2 - hydroxy introduction of the Schiff base 8f and 9f fluorescence intensity, fluorescence quantum efficiency is significantly improved; 4 - hydroxy little effect on the fluorescence spectra of Schiff base 9h made the Schiff base 8h decline in fluorescence intensity, the fluorescence quantum efficiency is reduced to about 1/3 of the unsubstituted Jixi Fu alkali. Introduction of electron withdrawing groups could easily cause fluorescence quenching, reducing the fluorescence quantum efficiency of the Schiff base. Linear relationship, but when the concentration of Schiff base 8f of the higher, the fluorescence intensity with increasing the concentration of DMSO and ethanol, in the fluorescence intensity and the concentration of the very dilute the concentration range Neixi Fu alkali 8f decline. Anhydrous ethanol, Cu2 the Schiff base 8f strong fluorescence sensitizing. (3) Synthesis of 4 - (4'-substituted phenylazo) salicylaldehyde azo compound, and then respectively with the first part of the synthesis of the two hydrazide prepared eight new azo-type Hydrazone class Schiff base. The structure of each compound characterized by 1H NMR spectroscopy, mass spectrometry, infrared spectroscopy and elemental analysis. The azo compound synthesis conditions were discussed, and the experimental results show that the temperature and acidity of the reaction.

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CLC: > Mathematical sciences and chemical > Chemistry > Physical Chemistry ( theoretical chemistry ),chemical physics > Structural Chemistry > Complex chemistry ( coordination chemistry )
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