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The Synthesis And Properties Of Boron Fluoride Fluorescent Dye

Posted on:2015-10-16Degree:MasterType:Thesis
Country:ChinaCandidate:Q CaoFull Text:PDF
GTID:2181330422475032Subject:Organic Chemistry
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Fluorescent dyes have been under widely research because of their applications invarious fields, and they have played important roles in development of advanced scienceand technology. The Boron-dipyrromethene fluorescent dye known as BODIPY is a kindfluorescent dye with higher molar absorptivity, narrow absorption and emission peak, highoptical and chemical stability and high fluorescence quantum yield. However, typicalBODIPYs have two serious disadvantages: non-emission in solid state and small Stokesshift.This paper took a multi-heterocyclic substituted pyrroles to committe to synthesisboron fluoride fluorescent dyes (Boron2-2`-pyridyl imidazole, referred BOPIM), withhigh quantum yield, larger Stokes shift (70nm above) and good fluorescence emissioncharacteristics in solution, solid, crystal morphology, which can be used for thephotovoltaic device. First, routes of the different synthetic have been designed to exploresuitable synthetic methods: A convenient multicomponent protocol has been developed forthe synthesis of various poly substituted2-(pyridin-2-yl)imidazoles from2-cyanopyridine,corresponding aromatic aldehydes and NH4OAc,then coordinated with BF3.OEt2.Solid-emissive BOPIM dyes bearing different electron donating and withdrawinggroups were synthesized. They emit fluorescence with large Stokes shift in solution andalso in solid state. The test of photochemical and photophysical properties results showedthat the end of the electronic effect of substituents on the performance of the spectrumhave a greater regulatory role. Electron donor (methoxy group) leads to red-shift of theabsorption and emission with higher fluorescent quantum yield, and electron acceptor(nitro group) plays the reverse role. The end of the steric substituent groups on thefluorescence properties of the dye also has a weak effect.BOPIM fluoroboric fluorescent dye form intermolecular hydrogen bonds with thecarboxyl constructed based on supramolecular self-assembly of hydrogen. Self-assembledbetween the rhodamine molecules took effective resonance fluorescence energy transfer(FRET), to give a red light emitting material in the solid state.Fluorescent dyes may also be regulated by the diarylethene photochromic. Ringintramolecular hydrogen bonds were formed between diarylethene ligand and9-anthraceneacid by supramolecular self-assembly. Under UV irradiation, diarylethene ligands closedloop, generating new peaks. Diarylethene with9-anthracene carboxylic acid by hydrogenbond formation through the light,9-anthracene acid absorption peak intensity will be increased as the light time allows further, so as to achieve regulation light-emittingproperties of9-anthracene carboxylic acid functionality.
Keywords/Search Tags:BOPIM, Stokes shifts, solid state light-emitting, FRET
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