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Symmetric benzimidazole ruthenium complex and preparation method thereof

A technology of benzimidazole and ruthenium complexes, applied in the field of synthetic chemistry, can solve the problems of long time, complicated process, and relatively difficult product purification, and achieve sensitive response, low cost, improved conversion rate and target product purity Effect

Active Publication Date: 2015-03-11
KUNMING UNIV OF SCI & TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] The commonly used synthetic method of ruthenium complexes is usually to use ruthenium trichloride and other ruthenium source materials as starting materials, under normal pressure conditions, carry out several complexation reactions by heating and reflux, and obtain specific ligands and ruthenium. Complexes, usually the method for synthesizing ruthenium complexes is complicated, takes a long time and is difficult to purify the product

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  • Symmetric benzimidazole ruthenium complex and preparation method thereof

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Embodiment 1

[0033] Example 1: Symmetric benzimidazole ruthenium complexes, characterized in that: the ruthenium complexes use symmetrical phosphoric acid groups at both ends as immobilizing ligands, and the three N atoms on the imidazole ring of the benzimidazole derivatives are The metal ruthenium ion is coordinated to form a complex, and its chemical structure is as follows:

[0034] .

[0035] The specific steps of the preparation method of the symmetrical benzimidazole ruthenium complex are as follows:

[0036] (1) Synthetic ligand 1-bromomethyl-3,5-bis(diethylphosphonate methyl)-2,4,6-trimethylbenzene, denoted as PO(OEt) 2 Br

[0037] Dissolve 5g, 12.53mmol of 2,4,6-tribromomethyltrimethylbenzene in 25ml of m-xylene in the reactor, add 4.57g, 25.06mmol of triethyl phosphate (2,4,6- The molar ratio of tribromomethyltrimethylbenzene to triethyl phosphate is 1:2) It is dissolved in 25ml of meta-xylene and dropped into the reactor, heated and stirred at 90°C for 20h, and then the solvent is di...

Embodiment 2

[0045] Example 2: Symmetric benzimidazole ruthenium complex, characterized in that: the ruthenium complex uses symmetrical phosphoric acid groups at both ends as the immobilizing ligand, and the three N atoms on the imidazole ring of the benzimidazole derivative are The metal ruthenium ion is coordinated to form a complex, and its chemical structure is as follows:

[0046] .

[0047] The specific steps of the preparation method of the symmetrical benzimidazole ruthenium complex are as follows:

[0048] (1) Synthetic ligand 1-bromomethyl-3,5-bis(diethylphosphonate methyl)-2,4,6-trimethylbenzene, denoted as PO(OEt) 2 Br

[0049] Dissolve 4.2g, 10.53mmol of 2,4,6-tribromomethyltrimethylbenzene in 23ml of m-xylene in the reactor, add 4.22g, 23.16mmol of triethyl phosphate (2,4,6 -The molar ratio of tribromomethyltrimethylbenzene to triethyl phosphate is 1:2.2) Dissolve it in 23ml of meta-xylene and drop it into the reactor. Heat and stir at 100°C for 24h, then distill the solvent under ...

Embodiment 3

[0055] Example 3: Symmetric benzimidazole ruthenium complexes, characterized in that: the ruthenium complexes use symmetrical phosphoric acid groups at both ends as immobilizing ligands, and the three N atoms on the imidazole ring of the benzimidazole derivatives are The metal ruthenium ion is coordinated to form a complex, and its chemical structure is as follows:

[0056] .

[0057] The specific steps of the preparation method of the symmetrical benzimidazole ruthenium complex are as follows:

[0058] (1) Synthetic ligand 1-bromomethyl-3,5-bis(diethylphosphonate methyl)-2,4,6-trimethylbenzene, denoted as PO(OEt) 2 Br

[0059] Dissolve 3.5g, 8.77mmol of 2,4,6-tribromomethyltrimethylbenzene in 20ml of m-xylene in the reactor, add 4.47g, 24.56mmol of triethyl phosphate (2,4,6 -The molar ratio of tribromomethyltrimethylbenzene to triethyl phosphate is 1:2.8) dissolved in 20ml of meta-xylene and dropped into the reactor, heated and stirred at 120°C for 30h, and then distilled under red...

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Abstract

The invention discloses a symmetric benzimidazole ruthenium complex and its preparation method and belongs to the technical field of synthetic chemistry. According to the preparation method, 2,4,6-trismesitylene and triethyl phosphate are used as starting materials, a fixed ligand is synthesized by a two-step method, and the fixed ligand finally reacts with ruthenium trihydrate under the microwave condition so as to synthesize the target product. The synthesized symmetric benzimidazole ruthenium complex has excellent stability and optical and electrochemical properties. Through covalent bond effect between symmetric phosphate groups at two ends of the molecule and the surface of a conductive substrate such as ITO and the like, the symmetric benzimidazole ruthenium complex molecule is fixed to the conductive substrate and layer-by-layer self-assembly is realized. The symmetric benzimidazole ruthenium complex is an excellent photosensitizer. In addition, the designed synthesis process of the symmetric benzimidazole ruthenium complex is simple, costs are low, and the microwave-assisted synthesis technology is rapid and efficient.

Description

Technical field [0001] The invention relates to a symmetrical benzimidazole ruthenium complex and a preparation method thereof, and belongs to the technical field of synthetic chemistry. Background technique [0002] In recent years, more and more researchers have begun to introduce various metal ions (main group metals, transition metals, and rare earth metals) into organic compounds, causing great changes in the photophysical and chemical properties of the system. Such complexes not only have the good luminescence properties of metal complexes, but also have the excellent material properties of organic compounds themselves, which greatly expands the applications of such materials in solar conversion, molecular catalysis, luminescence, information storage and other fields. [0003] As ruthenium complexes have the characteristics of good thermodynamic stability, rich photochemical and photophysical information, high excited state reaction activity, long life and good luminescence p...

Claims

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Application Information

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IPC IPC(8): C07F9/6558C09B57/10
Inventor 王华杨丽李孔斋魏永刚祝星
Owner KUNMING UNIV OF SCI & TECH
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