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Study Of Electrogenerated Chemiluminescence Property Of Indole Derivative Molecules

Posted on:2014-04-18Degree:MasterType:Thesis
Country:ChinaCandidate:J L LiuFull Text:PDF
GTID:2251330425996950Subject:Applied Chemistry
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In this paper, we investigated the electrochemiluminescence (ECL) of some heterocyclic organic molecules, and specifically studied the electrogenerated chemiluminescence of some indole carboxylic acid and the indole-based organic compounds with electron-withdrawing group on the5-position in detail. Their electrochemiluminescence conditions were optimized and the substituent’s impact on ECL of indole was discussed. At last we proposed a possible ECL reaction pattern and mechanism. In another experiment, we synthesized a kind of core-shell structure magnetic mesoporous silicon nanoparticles and designed a stimulus-response controlled release drug carrier which based aptamer-capped MMSNs. Depending on specifically recognition between aptamer and target cell, the application of this drug delivery carrier in targeted drug release in vitro was studied. The detail contents are listed below:1. ECL substrates selection from some N-heterocyclic organic small molecules.The electrochemiluminescence of some nitrogen-containing heterocyclic organic molecules was studied in this chapter. After comparison and analysis of their electrochemiluminescence data, several heterocyclic small molecule monomers have a strong and stable ECL signal were selected out for further studying. By analysis of their structure, we found the compounds with good ECL signal all have the indole-based structure, including indole, indole-3-carboxylic acid, indole-5-carboxylic acid, indole-5-formaldehyde and indole-5-carboxylate. So we first optimized the ECL condition of Indole monomer in ACN:0.05mol/L Bu4NPF6as supporting electrolyte, cyclic voltammetry potential was-2.2-0.2V,.scan speed was0.2V/s. under this condition, ECLmax potential was-0.2V.2. Study of the electrochemiluminescence of some indole carboxylic acid.In this chapter we investigated the electrochemiluminescence of some indole carboxylic acid organic small molecules, optimized the ECL condition of indole-3-carboxylic acid and indole-5-carboxylic acid and determined their maximum emission wavelength under optimized condition. Optimum condition of indole-3-carboxylic acid is:scanning potential-2.2-0.1V in0.5mol/L Bu4NFP6acetonitrile solution, scan rate0.2V/s, the maximum ECL potential-0.25V. Optimum condition of indole-5-carboxylic acid is:scanning potential-2.2-0.2V in0.05mol/L Bu4NFP6ACN solution, sweep speed0.3V/s, the maximum ECL potential-0.18V. Through other means of characterization and molecular structure level analysis, we proposed a possible ECL reaction mechanism of3-electron-withdrawing substituted indole-3-carboxylic acid.3The electrochemiluminescence study of5-substituted indole organic molecules.In this chapter we studied ECL of several5-electron-withdrawing substituted indole monomers and optimized5-formyl-indole and methyl indole-5-carboxylate and determinated the maximum ECL emission wavelength under optimized conditions. The optimum conditions ECL5-formyl-indole:scanning potential-2.2-0.2V in0.1mol/L BU4NFP6ACN solution, scan rate0.2V/s, the maximum ECL potential was0.11V; methyl indole-5-carboxylate’s optimization conditions:0.05mol/L BU4NFP6acetonitrile solution as supporting electrolyte, scan potential-2.2-0.2V, sweep speed0.2V/s, under this conditions the maximum emission potential was0.01V. We proposed a possible ECL reaction mechanism of5-position substituted indole with electron-withdrawing group and discussed the relationship between ECL and polymerization reaction, summarized the influence of substituents on the indole ECL reaction mechanism.4. Targeted controlled release system based on magnetic mesoporous silica.In this chapter we prepared APTS functionalized core-shell magnetic mesoporous silica composite microspheres. After loading ruthenium fluorescent dye, capped the mesopore with Ramos aptamer relying on the electrostatic adsorption to prevent the release of the guest molecules. Due to the specificity of the aptamer with target cell binding target Ramos cells and induced endocytosis. After competition off aptamer, opened pores and released the loaded guest molecules. With the help of CLSM, we evaluated the effect of the drug delivery carrier of such a cell targeted stimulus-response controlled release system in vitro. The result suggested that this system with good features of "zero premature release" and "controllable release", but also showed magnetic-aptamer dual targeting effect and could be used in tumor targeting and drug delivery.
Keywords/Search Tags:Electrochemiluminescence, Indole, Magnetic mesoporous silica, Controlled release, Drug delivery
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