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Study Of The Synthesis Of Functional Compounds Containing Imidazole Ring And The Determination Of Their Luminescent Properties

Posted on:2013-12-04Degree:MasterType:Thesis
Country:ChinaCandidate:B Z LiFull Text:PDF
GTID:2231330371485500Subject:Organic Chemistry
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Imidazole is one of the most important heterocyclic compounds including rich πelectron, which is amphoteric compounds. Imidazole play an important role inbiochemistry, material chemistry including luminescent material and protonconductivity material, medicinal chemistry and the determination of heavy metal iondue to that possess good thermal stability, transmitting electrons and protons, highreactive active, and excellent pharmaceutical, etc. Herein, the synthesis oftri-substituted imidazole were explored from benzoin carboxylates. Futher, newtetra-substitutied imidazole derivative containing furan rings were synthesized. Thesesynthesized compounds will bring high value-added and bright application prospect inchemical production.Firstly,2-hydroxy-1,2-diarylethanone were synthesized with the aromaticaldehydes as raw material in the presence of the catalyst VB1. And then,2-hydroxy-1,2-diarylethanone reacted with different acylating reagents under mildreaction conditions, benzoin carboxylates were obtained in excellent yields (88.5%–96.2%).Secondly,2-substituted-4,5-di(aryl)imidazoles were produced from benzoincarboxylates on solid supports alumina as a dispersant impregnated with ammoniumacetate in the yield of38.5%–83.3%, and seven of them have not been reported. Thesynthesized compounds were characterized by IR, HRMS and1H and13C NMRspectral. All compounds were characterized to determine their structures and thereaction mechanism was proposed.Thirdly,2-substituted-4,5-di(aryl)imidazoles as a material, to explore thenitrogen of trisubstituted imidazoles containing furan rings to introduce the fourthsubstituted groups. The reaction of trisubstituted imidazole and benzyl chloride inanhydrous THF was investigated, As a result, fifteen new imidazole compoundscontaining furan rings were synthesized in better yield59.0%89.8%. Thesynthesized products were characterized by IR, elemental analysis, HRMS spectra,1HNMR and13C NMR. In addition, Imidazole ring is considered as good organic non-linear opticalmaterial owing to its special nature. Therefore, the UV–vis and photoluminescencespectra of the synthesized compounds were mensurated, the fluorescence quantumyields were calculated, which is the groundwork for the further application of furanderivatives to optical materials.
Keywords/Search Tags:trisubstituted imidazoles, tetrasubstituted imidazoles, aromaticaldehydes, 2-hydroxy-1, 2-diarylethanone, organic synthesis, luminescent property
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