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Study on the Synthesis, Characterization, Chemiluminescent Properties of Novel Compounds Containing Nitrogen Atoms & Phosphomonoesters

Author: HeXiaoLian
Tutor: WeiQingLi；YangXiaoYan
School: Qingdao University of Science and Technology
Course: Organic Chemistry
Keywords: Chemiluminecence Compounds containing nitrogen atoms Phosphomonoesters Proenhancer Inhibitor Synthesis Characterization
CLC: O627.51
Type: Master's thesis
Year: 2008
Downloads: 125
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Abstract


This paper describes the recent development of the chemiluminecence principles and applications; the synthesis and reaction mechanism of para-derivatives of phenol containing C-N bonds; the synthesis of phosphomonoesters and aromatic Schiff Bases derivatives containing C=N bonds.The active groups of aromatic imine were induced into the target compounds according to the effect of Ferrocene metal catalyst containing diphenylphosphine complex with huge bulk. Five para-derivatives of phenol containing C-N bonds were designed and synthesized. They are 4-（1H-benzo[d]-1-yl）phenol（A1）; 4-（1H-benzo[d] -[1,2,3]triazole-1-yl）phenol（A2）; 4-（9H-carbazol-9-yl）phenol（A3）; 4-（di（1H-indol-2 -yl）-methyl）phenol（A4）; 4-（1H-benzo[d]imidazol-2-yl）phenol（A5）, respectively. Six aromatic Schiff Bases derivatives containing C=N bonds were designed and synthesized. They are 4-ethoxy-N-（3-（2-nitrophenyl）allylidene）benzenamine（B1）; N-（3-（2-nitrophenyl）-allylid-ene）naphthalene-1-amine（B2）; 4-methoxy-N-（3-（2-nitro -phenyl）allylidene）-benzenamine（B3）; 4-ethoxy-N-（3-phenylallylidene）Benzene -amine（B4）; 4-methoxy-N-（-3-phenylallylidene）benzeneamine（B5）; 2-methoxy-N-（3- （2-nitrophen-yl）allylidene）benzeneamine（B6）, respectively. Four single crystals of four kinds of compounds were got. Five phosphomonoesters were designed and synthesized. They are 4-iodophenol phosphate monoester（C1）; 4-phenylphenol phosphate monoester（C2）; 4-（4’-hydroxy）phenylphenol phosphate monoester（C3）; 4-（4’-iodo）phenylphenol phosphate monoester（C4）; 4-（1H-1,2,4-triazol-1-yl）phenyl -phenol phosphate monoester（C5）, respectively. The structures of the novel compounds synthesized were confirmed by means of IR, 1H-NMR, 13C-NMR and X-ray single-crystal diffraction method determination. The fluorescent effects and chemiluminecent effects of the products were tested so as to select the high-activity compounds. The fluorescent effects of the new kinds of para-derivatives of phenol were tested, and the results showed that most of the compounds have high fluorescent activities. It is well known that the fluorescent effects of the molecules are influenced by the substituted groups and conjugated degree.4-（1H-benzo[d]imidazol-2-yl）phenol（A5） was used in the luminol-H2O2-HRP system as anti-enhancer. As the results shown, it is a potent inhibitor in the luminol-H2O2-HRP. The optimal experiment conditions are as follows: [Luminol]: 5×10-5 mol/L（0.1 mol/LTris-HCl, pH=8.6）; [HRP]: 1×10-5 mg/mL; [H2O2]: 5×10-3 mol/L; [A5]: 1.0×10-3 mol/L; Tris buffer 0.1 mol/L, pH 8.6.It can be concluded from our results that 4-（1H-1,2,4-triazol-1-yl）phenylphenol phosphate monoester（C5） can be used in the luminol-H2O2-HRP system as pro-enhancer. As the results showed, it was a potent proenhancer in the luminol-H2O2-HRP. The optimal experiment conditions are as follows: [Luminol]: 2.0×10-4 mol/L（0.1 mol/LTris-HCl, pH=8.6）; [ALP]: 1×10-4 mg/mL; [phosphomonoester]: 1.0×10-3 mol/L; [H2O2]: 1×10-3 mol/L; Tris buffer 0.1 mol/L, pH 8.6. The phosphomonoester and ALP were incubated in water for 30 minutes.Under these conditions the ALP-enzymatic hydrolysis of phosphomonoester was complete and the enhancement of the light emission was remarkably. The time of light emission was prolonged. The effect of the chemiluminecence was 200 times more than the blank.

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CLC: > Mathematical sciences and chemical > Chemistry > Organic Chemistry > Elements in organic compounds > Section Ⅴ group elements, organic compounds ( nitrogen) > Phosphorus in organic compounds
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