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N-heterocyclic dicarbene metal complex connected with ether chain, method for preparing same and use

A nitrogen heterocyclic carbene and metal complex technology, applied in the direction of mercury organic compounds, copper organic compounds, silver organic compounds, etc., can solve problems such as metal complex research only, achieve adjustable structure, obvious fluorescence photosensitive effect, Prepare concise effects

Inactive Publication Date: 2008-11-19
TIANJIN NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

1968 and Wanzlick et al. discovered metal complexes 1 and 2 of N-heterocyclic carbene, but they were limited to metal complexes

Method used

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  • N-heterocyclic dicarbene metal complex connected with ether chain, method for preparing same and use
  • N-heterocyclic dicarbene metal complex connected with ether chain, method for preparing same and use
  • N-heterocyclic dicarbene metal complex connected with ether chain, method for preparing same and use

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0053] 1,2-bis(2'-iodoethoxy)ethane (1.500 g, 4.0 mmol) and 1-ethylbenzimidazole (1.304 g, 8.9 mmol) were added to 1,4-dioxane, After stirring at 90°C for 3 days, a white precipitate precipitated out, which was filtered and washed with ether to obtain a white powder of 1,2-bis[2'-(3-ethylbenzimidazole)ethoxy]ethane iodide. Yield: 2.060 g (76.6%), Mp: 192-194°C. 1 H NMR (300MHz, DMSO-d 6 ): δ1.62 (t, J=5.5, 6H, CH 3 ), 3.36(t, J=4.2, 4H, CH 2 ), 3.78(t, J=4.2, 4H, CH 2 ), 4.72(t, J=4.2, 4H, CH 2 ), 4.86 (q, J=5.5, 4H, CH 2 ), 7.68 (m, 4H, PhH), 7.90 (d, J=6.3, 2H, PhH), 7.97 (d, J=6.3, 2H, PhH), 11.50 (s, 2H, 2-benzimiH) (benzimi= benzimidazole).

[0054] The experimental process is shown in the figure below:

[0055]

preparation example 2

[0057] 1,2-bis(2'-iodoethoxy)ethane (1.500 g, 4.1 mmol) and 1-pyridylbenzimidazole (2.044 g, 8.9 mmol) in 1,4-dioxane, Stirring at 90°C for 3 days, a white precipitate precipitated, filtered and washed with ether to obtain 1,2-bis[2'-(3-(2"-pyridylmethyl)benzimidazole)ethoxy]ethane iodide Compound as a white powder. Yield: 2.540 g (75.6%), Mp: 156-158°C. 1 H NMR (300MHz, DMSO-d 6 ): δ3.76 (t, J=4.2, 4H, CH 2 ), 4.74(t, J=4.2, 4H, CH 2 ), 4.85(t, J=5.5, 4H, CH 2 ), 5.93 (s, 4H, CH 2 ), 7.39(m, 2H, PhH), 7.66(m, 6H, PhH or PyH), 7.93(m, 4H, PhH or PyH), 8.18(m, 2H, PyH), 8.46(d, 2H, PyH) , 9.87 (s, 2H, 2-benzimiH) (benzimi=benzimidazole).

[0058] The experimental process is shown in the figure below:

[0059]

preparation example 3

[0061] Bis(2-iodoethyl)ether (5.000g, 0.015mol) and 1-ethylbenzimidazole (4.930g, 0.034mol) in 1,4-dioxane were stirred at 90°C for 3 days, A white precipitate precipitated, was filtered and washed with ether to obtain a white powder of bis[2-(3-ethyl)benzimidazole]ether iodide. Yield: 7.460 g (78.7%), Mp: 172-174°C. 1 H NMR (300MHz, DMSO-d 6 ): δ1.64 (t, J=5.5, 6H, CH 3 ), 3.41 (q, J = 4.2, 4H, CH 2 ), 3.71(t, J=4.2, 4H, CH 2 ), 4.77(t, J=4.2, 4H, CH 2 ), 7.70 (m, 4H, PhH), 7.92 (d, J=6.4, 2H, PhH), 7.94 (d, J=6.4, 2H, PhH), 11.23 (s, 2H, 2-benzimiH) (benzimi= benzimidazole).

[0062] The experimental process is shown in the figure below:

[0063]

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Abstract

The invention discloses a cyclic N-heterocyclic bis-carbene metal complex linked by ether and a method for preparing the same. The method comprises the steps of: adding imidazole or benzimidazolium salt linked by the ether and a metallic compound into a reactor according to the mol ratio of 0.5 to 3-2 to 5mol, under the protection of inert gas; and reacting for 12 to 24 hours at a temperature of between 0 and 100 DEG C, after dissolving the mixture by a dewatered high-purity organic solvent; filtering and naturally volatilizing the reacted mixture and solvent to produce a carbene metal complex. The cyclic N-heterocyclic bis-carbene metal complex linked by the ether, which is prepared with the method, is mainly used for preparing fluorescent materials.

Description

[0001] Statement Regarding Funding Research or Development [0002] The present invention is carried out under the support of National Natural Science Foundation of China (fund number 20672081) and Tianjin Natural Science Foundation (fund number 07JCYBJC00300). technical field [0003] The invention belongs to the technical field of organometallic chemistry, and relates to N-heterocyclic biscarbene metal complexes connected by ether chains. More specifically, it is a metal complex of N-heterocyclic biscarbene mercury and silver and its preparation method. And research on the fluorescence properties of N-heterocyclic biscarbene silver metal complexes. Background technique [0004] Since Fischer et al. introduced carbenes into inorganic and metal organic chemistry in 1964, metal carbenes have been widely used in organic synthesis (as reagents and catalysts) and polymer chemistry. 1968 and Wanzlick et al. found metal complexes 1 and 2 of N-heterocyclic carbene, but they wer...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F3/10C07F1/08C07F1/10C07D235/08C09K11/06
Inventor 柳清湘刘书文吴秀梅臧燕
Owner TIANJIN NORMAL UNIVERSITY
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