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ECL marker of binuclear bipyridyl ruthenium/osmium connected by saturated carbon chains of different lengths

A technology of nuclear bipyridyl ruthenium and markers, applied in the field of binuclear bipyridyl ruthenium/osmium ECL markers, can solve the problems of small number of reactive centers and low electron transfer efficiency, and achieve the effect of enhancing ECL intensity

Inactive Publication Date: 2009-09-30
DALIAN UNIV OF TECH
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  • Abstract
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Problems solved by technology

[0009] The purpose of the invention is to improve Ru(bpy) in the existing blend system 3 2+ -The number of reactive centers in the amine co-reactant system is small, the electron transfer efficiency of the intermolecular interaction is low, and the shortcomings of a large excess of amine co-reactants must be used to provide a simple method that can reduce the amount of amine co-reactants Connect two Ru(bpy) with saturated carbon chain 3 2+ Molecular formation of dinuclear bipyridyl markers that can significantly enhance the intensity of electrochemiluminescence

Method used

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  • ECL marker of binuclear bipyridyl ruthenium/osmium connected by saturated carbon chains of different lengths
  • ECL marker of binuclear bipyridyl ruthenium/osmium connected by saturated carbon chains of different lengths
  • ECL marker of binuclear bipyridyl ruthenium/osmium connected by saturated carbon chains of different lengths

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Experimental program
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Embodiment 1

[0026] Synthesis method of ECL marker Ru-8c-Ru:

[0027] The reaction formula is as follows:

[0028]

[0029] (1) Synthesis of Intermediate 1:

[0030] The methyl lithiation and subsequent 1,6-dibromohexane substitution reaction strictly followed the Schlenk procedure. Mix 2.67ml (5.88mmol) of 2.2mol / L n-butyllithium n-hexane solution with 0.82ml dehydrated diisopropylamine (5.88mmol) to prepare lithium diisopropylamide solution (LDA). 1g of 4-methyl-2,2'-bipyridine (5.88mmol) was dissolved in 40ml of dehydrated THF, and the previously prepared LDA solution was injected, and after 1 hour of reaction, 0.5ml of 1,6-dibromohexane was added. After reacting for 3 hours, stop the reaction with 50ml of phosphate buffer (pH=7), extract with dichloromethane (3×50ml), dry the organic phase over anhydrous sodium sulfate, and separate by silica gel column chromatography (dichloromethane-ethyl acetate ester, 10:1) to obtain 1.05 g of white solid, yield 85%.

[0031] (2) Synthesis o...

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Abstract

The invention belongs to the field of fine chemical industry, in particular to an ECL marker of binuclear bipyridyl ruthenium / osmium connected by saturated carbon chains of different lengths. The binuclear pyridine ruthenium / osmium ECL marker has structural general formula of L2M-L'-M'(L)2, wherein M and M' are Ru or Os, L is selected from 2,2'-bipyridyl and the derivate thereof or 1,10-o-phenanthroline (naphthisodiazine) and the derivate thereof, L' is selected from the ligand having the formula in the above figure, in the formular, n is a whole number from 7 to 20, the total carbon number of alkyl chains is a whole number from 7 to 20, and A is a methyl group (-CH3) or H. For the marker, 4-methyl bipyridyl is used as raw material, and the double-bipyridyl ligand connected by saturated carbon chains of different lengths is compounded by the 4-methyl bipyridyl after methyl lithiation and the substitution reaction of dihalogenated substance, and the double-bipyridyl ligand is processed by complexation reaction with metal ruthenium or osmium. The saturated soft carbon chains of different lengths are used as connecting arms, and the binuclear bipyridyl ruthenium / osmium molecular containing two metal cores is compounded. Compared with the traditional mononuclear terpyridyl ruthenium Ru(bpy)3<2+>, and in the ECL check under the synergic action of amine coreaction agents, the ECL strength of the binuclear bipyridyl ruthenium / osmium molecular is obviously improved.

Description

technical field [0001] The invention belongs to the field of fine chemical industry, and specifically relates to a class of dinuclear bipyridyl ruthenium / osmium ECL markers connected by saturated carbon chains of different lengths. Background technique [0002] Electrochemiluminescence Electrogenerated chemiluminescence (also known as electrochemiluminescence, ECL) is the electroactive species generated on the electrode surface undergoes an electron transfer reaction to form an excited state, and then the energy of the excited state is released in the form of light. In practical applications, the most widely used luminescent substance is terpyridine ruthenium metal complex. With the increasing field of modern analytical science, how to enhance Ru(bpy) 3 2+ ECL strength and further improvement of detection sensitivity have become one of the key issues to be solved urgently. The establishment of a binuclear and multinuclear ruthenium metal complex system is to introduce more...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C07D213/22C07D471/04G01N21/66
Inventor 孙世国杨洋樊江莉彭孝军刘凤玉
Owner DALIAN UNIV OF TECH
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