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Synthesis And Properties Of Chiral Dyes Based On Binol

Posted on:2019-05-03Degree:MasterType:Thesis
Country:ChinaCandidate:W LiuFull Text:PDF
GTID:2321330566965834Subject:Organic Chemistry
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Most conventional fluorescent emitters have high-intensity fluorescent properties in dilute solutions,but have very weak fluorescence or have no fluorescence in an as-growth or solid state,it is a phenomenon known as aggregation-induced quenching(ACQ).In recent years,some compounds that are different from conventional dyes have been reported.In dilute solutions,the fluorescence intensity is weak and even the fluorescence is not detectable.However,when the fluorescent emitter is in a high concentration or in a solution state,it will make the fluorescence more stable.A large degree of improvement,this phenomenon is called aggregation induced light(AIE).At the same time,many of them have good fluorescence,but the fluorescence will be further enhanced in the aggregated state,and these compounds have the property of aggregation-induced fluorescence enhancement(AEE).Compared with aggregation-induced fluorescence quenching fluorescent dyes,aggregation-induced luminescence materials have more potential applications in cell staining,light-emitting diodes,drug delivery and other fields.The second chapter of this article mainly focuses on the synthesis of coumarin fluorescent dyes with axial chirality for the first time.The properties of the synthesized compound 1-4(R-type)were found to have good aggregation-induced fluorescence enhancement characteristics,and the fluorescence intensity in tetrahydrofuran solution increased with more water content.The fluorescence intensity and water content presenting a good linear relationship.Chemical materials with aggregation-inducing properties have been widely used in the fields of physics,optoelectronics,and biomedicine.The synthetic axial chiral coumadin dyes used in this paper are simple at the same time have high yields and good stability.These conditions make Compounds 1-4 have good application prospects.In the third chapter,2,7-dihydroxynaphthalene was used as the basic raw material to synthesize 7,7'-dimethylamine-binadioldiol substituted by dimethylamine substitution and coupling,and then used as the intermediate product.A series of compounds,such as bis-naphthalene bisphenol coumarin and coumarin substituted at the 7,7? position,were synthesized.Using XRD,DSC and other analytical methods to analyze the solid sample before and after rolling,it is known that the piezochromic properties of this type of compound is due to the destruction of its crystal structure under the action of external forces,so the color will change after rolling..The synthesized compound 2-6 was resolved to give a chiral product.The amide compounds change color from yellow to yellow-green after rolling,and the fluorescence emission peak undergoes a slight blue shift,and the initial state is not recovered by fumigation with different solvents.In comparison,the viscosity of coumarin esters is better,and the color change of the product before and after rolling can be clearly identified with the naked eye.
Keywords/Search Tags:Chirality, BINOL, Coumarin, AIE, Piezochromic
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