A kind of conjugated ligand bridged diarylamine and ruthenium acetylene terminal compound and application thereof

A technology of diarylamines and compounds, applied in the field of organic synthesis

Active Publication Date: 2021-02-23
HENGYANG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Ruthenium metal end groups and triarylamines have excellent electrochemical activity and stability. If the excellent properties of the two can be combined and a compound with strong electronic interaction between the end groups can be synthesized, it will greatly improve the Promote the development of molecular wire materials, but no relevant reports have been found in the prior art

Method used

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  • A kind of conjugated ligand bridged diarylamine and ruthenium acetylene terminal compound and application thereof
  • A kind of conjugated ligand bridged diarylamine and ruthenium acetylene terminal compound and application thereof
  • A kind of conjugated ligand bridged diarylamine and ruthenium acetylene terminal compound and application thereof

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Experimental program
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Effect test

Embodiment 1

[0053]A kind of conjugated ligand bridged diarylamine and ruthenium acetylene terminal compound, its structural formula I-1 is as follows:

[0054]

[0055] The method for preparing the diarylamine and ruthenium acetylene terminal compound bridged by the conjugated ligand comprises the following steps:

[0056] a. Under the protection of nitrogen, 0.3mmol (1,2-bisdiphenylphosphinoethane) ruthenium chloride Cp * Ru(dppe)Cl, 0.25mmol 4-trimethylsilylethynyl-N,N-bis(4-methoxyphenyl)-1-aniline) and 2mmol potassium fluoride were dissolved in 20ml methanol and 3-4ml In the mixed solution of tetrahydrofuran, cool to room temperature after heating to reflux for 24h;

[0057] b. suction filtration, the resulting solids were washed with 10ml of methanol and 10ml of n-hexane, and then recrystallized with dichloromethane and n-hexane;

[0058] c. Acetone and petroleum ether with a volume ratio of 1:2 were selected as eluents for column chromatography to obtain 150 mg of yellow crysta...

Embodiment 2

[0065] A kind of conjugated ligand bridged diarylamine and ruthenium acetylene terminal compound, its structural formula I-2 is as follows:

[0066]

[0067] The method for preparing the diarylamine and ruthenium acetylene terminal compound bridged by the conjugated ligand comprises the following steps:

[0068] a. Under nitrogen protection, 0.3 mmol pentamethylcyclopentadienyl (1,2-bisdiphenylphosphine ethane) ruthenium chloride Cp * Ru(dppe)Cl, 0.25mmol 3-trimethylsilylethynyl-N,N-di(4-methoxyphenyl)-1-aniline) and 2mmol potassium fluoride were dissolved in 20ml methanol and 3-4ml In the mixed solution of tetrahydrofuran, cool to room temperature after heating to reflux for 24h;

[0069] b. suction filtration, the resulting solids were washed with 10ml of methanol and 10ml of n-hexane, and then recrystallized with dichloromethane and n-hexane;

[0070] c. Acetone and petroleum ether with a volume ratio of 1:2 were selected as eluents for column chromatography separation...

Embodiment 3

[0077] A diarylamine and ruthenium acetylene terminal compound bridged by a conjugated ligand, its structural formula I-3 is as follows:

[0078]

[0079] The method for preparing the diarylamine and ruthenium acetylene terminal compound bridged by the conjugated ligand comprises the following steps:

[0080] a. 0.3mmol pentamethylcyclopentadienyl (1,2-bisdiphenylphosphine ethane) ruthenium chloride Cp * Dissolve Ru(dppe)Cl, 0.25mmol 4-trimethylsilylethynyl-N,N-bis(4-methoxyphenyl)-1-naphthylamine) and 2mmol potassium fluoride in 20ml methanol and 2ml tetrahydrofuran In the mixed solution, cool to room temperature after heating to reflux for 24h;

[0081] b. Suction filtration, the obtained solid was washed with 10ml of methanol and 10ml of n-hexane respectively, and then recrystallized with dichloromethane and n-hexane to obtain 180mg of a tea-green solid, yield: 68%.

[0082] The carbon nuclear magnetic resonance spectrum, the proton nuclear magnetic resonance spectrum ...

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Abstract

The invention discloses a conjugated ligand bridged diarylamine and ruthenium ethynyl-terminated compound and an application thereof. The conjugated ligand bridged diarylamine and ruthenium ethynyl-terminated compound is represented by formula I shown in the description; and in the formula I, R is H, Me or OMe, and the conjugated ligand Ar is a phenyl group, a naphthyl group or an anthracenyl group. A result of electrochemical method test shows that strong electronic interaction exists between the end groups of the compound, two consecutive single-electron redox processes can be presented, andthe potential difference deltaE can reach 496-540 mV. The conjugated ligand bridged diarylamine and ruthenium ethynyl-terminated compound can be widely used in molecular lead wire materials, and provides a new research idea for the future development of mixed redox active end group molecular wires and molecular electrons.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a conjugated ligand bridged diarylamine and ruthenium acetylene terminal compound and its application. Background technique [0002] Transition metal ruthenium end groups are widely used in the design of metal-organic molecular wires to study the electron transport ability of conjugated bridging ligands. Triarylamine and its derivatives are an important class of organic molecules, which are widely used in pharmaceutical intermediates, pesticides, dye chemicals, organic materials and other fields. Because of their excellent charge transport properties, they are often used as organic optoelectronic materials. Research. [0003] Ruthenium metal end groups and triarylamines have excellent electrochemical activity and stability. If the excellent properties of the two can be combined and a compound with strong electronic interaction between the end groups can be synthesized, it will g...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F15/00
CPCC07F15/0046
Inventor 欧亚平
Owner HENGYANG NORMAL UNIV
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