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Synthesis, Structure Characterization and Optical Properties Research of Pyrazoline Derivatives as Well as Zn2+ Fluorescent Sensors Exploration

Author: GongZhongLiang
Tutor: ZhaoBaoXiang
School: Shandong University
Course: Organic Chemistry
Keywords: Pyrazoline derivatives Synthesis Ultraviolet absorption spectrum Fluorescence spectroscopy The Zn2 fluorescent probe
CLC: O626
Type: Master's thesis
Year: 2011
Downloads: 90
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Abstract


Pyrazoline derivatives as an important class of nitrogen-containing five-membered heterocyclic compounds by more and more attention in the field of bio-medicine, dyes, hole material and fluorescent probes. These compounds not only has a wide range of biological activity, such as antibacterial anti-inflammatory, analgesic, anti-amoebic, anti-convulsant, anti-TB, anti-cancer, and inhibition of monoamine oxidase enzymes activity pyrazoline derivatives also good Blu-ray emission, high the quantum yield and the hole transport efficiency, and is widely used as a rayon fiber, leather and paper fluorescent whitening shiny agent, a fluorescent probe or a chemical sensor for the detection of metal ions, in the electronic photography of a hole transport material, organic light-emitting diode and a new type of fluorescent material. In view of the importance of pyrazoline derivatives in biomedicine and fluorescent materials, this paper is mainly focused on the synthesis of these compounds, the nature of the research and its application of fluorescent - fluorescent probe. Specific work mainly includes the following two aspects: (1) the synthesis of pyrazoline derivatives, Structural Characterization and optical properties of study and discussion 1.1 to containing different substituted phenyl chalcone and chloropyridazine hydrazine as raw material in the alkali synthesized a series of pyrazoline derivative sexual ethanol solution under reflux conditions, the structure of the product by 1H NMR, IR and HRMS characterized, wherein the structure of the compounds 3d obtained X-ray diffraction verified. Further, measured in a chloroform solution UV absorption and fluorescence emission spectroscopy and discussed substituent effects of its spectrum of the series of compounds; compound 3a, 3b, 3e and 3d, for example, were measured in THF, CHCl3 with and CH3CN three different solution spectrum and its spectral effects of the solvent effect. 1.2 ferrocenyl chalcone chloropyridazine hydrazine as the raw material, and synthesized a series of pyrazoline derivative in alkaline n-propanol solution under reflux conditions, the structure of the product by 1HNMR, IR and HRMS characterize the structure of compound 3c and 4c X-ray single crystal diffraction validation. Further, the UV absorption and fluorescence emission spectroscopy and discussed substituent effects of its spectrum of the series of compounds; compounds 3b and 3d, for example, were measured in a chloroform solution were measured in THF, CHCl3, and the CH3CN solution UV absorption spectroscopy and 3b and 4b, for example, were measured in CHCl3, CH3CN and CH3OH solution fluorescence spectroscopy and discussed the impact of the the solvent effect their spectroscopy. 1.3 containing various substituted phenyl the chalcone and sulfonyl (3,1 - phenylene)) bis (hydrazide) as raw materials, synthesized a series of diphenyl sulfone bridge in alkaline ethanol solution under reflux conditions The pyrazoline derivatives connection, the product structure by 1H NMR, IR and HRMS characterized, including X-ray single crystal diffraction structure of compound 3b verify. Further, UV absorption and fluorescence spectroscopy of the series of compounds were measured in dichloromethane solution and discuss substituent effects its spectral properties; compound 3c, for example, respectively, measured in toluene, CH2Cl2, ethyl acetate CH3CN, of C2H5OH and a DMF solution UV absorption and fluorescence spectroscopy and solvent effect of the spectral properties of the impact. 2. The pyrazoline derivatives the Zn2 fluorescent probe synthesis, structural characterization and its ion-selective 2.1 chlorophenol and pyridazine hydrazine as the starting material, the five-step synthesis of carboxyl-modified pyrazoline derivatives , and its structure was characterized by 1HNMR, IR and HRMS. In addition, its ion-selective study found that a mixed solution of acetonitrile and ethanol (9/1, v / v) of Zn2 preferably ion selective and anti-interference of other ions, through the Job curve determination and Zn2 fluorescence titration experiments a coordination number of known compounds 5 and Zn2 is 1, and the complexing constant of 2.5 × 106M-1, the fluorescence intensity of Compound 5 can be enhanced from about 6-fold when the above solution of the compound 5 was added to 1.0 equivalents of Zn2. 2.2 chlorophenol and 2 - aminopyridine as starting material, synthesized via multi-step reaction pyrazoline derivatives 4, and their structures were characterized by 1HNMR, IR and HRMS. In addition, its ion-selective research found in acetonitrile and water (1/1, v / v) HEPES buffer solution (pH = 7.2) for Zn2 preferably ion selective and anti-interference of other ions, through of Zn2 ' The median UV absorption and fluorescence emission titration experiment shows that compounds 4 and Zn2 'with 1 complexation constant of 2.87 × 106 M-1, the lowest detection limit of 1.2x10-7 M. While when in compound 4 of the above solution was added 1.0 equivalents of Zn2 the fluorescence quantum yield of the compound 4 can be increased by about 3.5 times. In short, we pyrazoline structural unit as the core unit, has synthesized three series of pyrazoline derivatives, while its UV absorption and fluorescence spectra study and discuss the substituent effect and solvent effect its spectral intensity and location of impact, for the future development of the application pyrazoline fluorescent material laid the foundation. In addition, on the basis of the fluorescence properties of pyrazoline derivatives were pyrazoline structure unit Zn2 'exploration of fluorescent probes, two pyrazoline the Zn2 fluorescent probe has been synthesized, and ion selective ion interference resistance and with Zn2 'coordination number, complexation constant physical parameters such as research and discussion, the development of a class can be applied to a mixed solution of acetonitrile and water in the qualitative and quantitative detection of Zn2' topiramate quinazoline class of fluorescent probes, and pointed out the direction for the future to continue to develop the aqueous solution can be applied to the efficient pyrazoline fluorescent probe.

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CLC: > Mathematical sciences and chemical > Chemistry > Organic Chemistry > Heterocyclic compounds
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