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Synthesis and properties of several organic free radicals based on perylene derivatives

Author: XuMaoYou
Tutor: ShiZhiQiang
School: Shandong Normal University
Course: Organic Chemistry
Keywords: perylene derivative fluorescence switch free radical Fe(III) Cu( II)
CLC: O621.2
Type: Master's thesis
Year: 2009
Downloads: 109
Quote: 1
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Abstract


As an important class of functional materials,perylene bisimide derivative possess many advantages of stable structure,oustanding photoelectron properties,high thermal stability and exhibit wide absorption and emission bands in the visible,which can be widely used in laser material,fluorescence probe,liquid crystal material,organic solid state photovoltaic device,organic thin-film field-effect transistor,organic solar cell and so on.In this paper,a series of novel fluorescence probe and organic magnets which based on perylene bisimides,have been designed and synthesized,and their photoelectron properties and magnetic properties have been studied.Four chapters were included in present thesis.Chapter 1:The synthesis,properties and applications of the perylene bisimide derivatives have been reviewed.The detection methods of free radicals and Fe(Ⅲ), Cu(Ⅱ) have also been reviewed.The thesis aims to the design of fluorescent probes based on perylene bisimides.Chapter 2:A series of novel fluorescence probes which based on perylene bisimides,have been synthesized in good yields in chapter 2.The compounds were studied in detailed with steady-state spectroscopy,dynamic-state spectroscopy and ESR spectrum.Compound 7 was a novel fluorescence probe for the determination of Fe(Ⅲ) in chemical system.It was designed by incorporating the nitroxide to perylene imide, which was proved to be high sensitive and selective.Featured in strong fluorescence above 500 nm the high fluorescence can be quenched by nitroxide through a PET mechanism and recovered rapidly by trapping Fe(Ⅲ),hydroxyl radical or ascorbic acid.Chapter 3:Two types of perylene imide derivatives containing 4-(1-(quinoxalin-2-yl)propylidenehydrazonomethylphenol substituents were synthesized.The high fluorescent perylene imide derivatives can be quenched by coordinating several metal ions.Among that,compound(9) demonstrated sensitivity to the Cu(Ⅱ).The mechanism was researched and a novel probe for the Cu(Ⅱ) was designed.Chapter 4:Several types of perylene imide derivatives containing 8-hydroquinoline substituents were synthesized.The high fluorescent perylene imide derivatives can be quenched by coordinating several metal ions.Among that,compound(11) demonstrated sensitivity to the Cu(Ⅱ).The mechanism was researched and a novel probe for the Cu (Ⅱ) was designed.

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CLC: > Mathematical sciences and chemical > Chemistry > Organic Chemistry > Organic Chemistry general issues > Properties of organic compounds
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