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Pyridine-bridged double-ruthenium acetylene terminal group compound and preparation method and application thereof

A pyridine bridged and compound technology is applied in the field of pyridine bridged bisruthenium acetylene end-group compounds and the preparation thereof, can solve problems such as the synthesis method of bisruthenium acetylene end-group compounds that have not been seen, and achieves good electronic interaction, good The effect of charge transport properties

Pending Publication Date: 2020-05-29
HENGYANG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, in the field of molecular wire materials, there have been no relevant reports on pyridine-bridged double ruthenium acetylene terminal compounds and their synthesis methods.

Method used

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  • Pyridine-bridged double-ruthenium acetylene terminal group compound and preparation method and application thereof
  • Pyridine-bridged double-ruthenium acetylene terminal group compound and preparation method and application thereof
  • Pyridine-bridged double-ruthenium acetylene terminal group compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Preparation of pyridine-bridged double ruthenium acetylene terminal compounds: under nitrogen protection, an appropriate amount of pentamethylcyclopentadienyl (1,2-bisdiphenylphosphineethane) ruthenium chloride Cp * Ru(dppe)Cl (preferably 500mg, 0.74mmol), 2,6-bis(trimethylsilylethynyl)pyridine (preferably 80mg, 0.30mmol) and potassium fluoride (preferably 205mg, 3.54mmol) were dissolved in an appropriate amount of methanol ( preferably 20ml) and tetrahydrofuran (preferably 3-4ml), the system is heated to reflux until the reaction is complete (about 24 hours), cooled to room temperature, suction filtered, and the solids are washed with 5-10ml methanol and 5-10ml n-hexane respectively , and then recrystallized with dichloromethane and n-hexane to obtain 250 mg of a brown solid with a yield of 57%. In the obtained pyridine-bridged double ruthenium acetylene terminal compound, R' is H, and the structural formula is: Its NMR spectrum is shown in Figure 1-3 shown.

[004...

Embodiment 2

[0046] Preparation of pyridine-bridged double ruthenium acetylene terminal compounds: under nitrogen protection, an appropriate amount of pentamethylcyclopentadienyl (1,2-bisdiphenylphosphineethane) ruthenium chloride Cp * Ru(dppe)Cl (preferably 500mg, 0.74mmol), 3,5-bis(trimethylsilylethynyl)pyridine (preferably 80mg, 0.30mmol) and potassium fluoride (preferably 205mg, 3.54mmol) were dissolved in an appropriate amount of methanol ( preferably 20ml) and tetrahydrofuran (preferably 3-4ml), the system is heated to reflux until the reaction is complete (about 24 hours), cooled to room temperature, suction filtered, and the solids are washed with 5-10ml methanol and 5-10ml n-hexane respectively , and then recrystallized with dichloromethane and n-hexane to obtain 267 mg of brown solid with a yield of 61%, and the structural formula of the double ruthenium acetylene terminal compound bridged by the gained pyridine is: Its NMR spectrum is shown in Figure 4-6 shown.

[0047] Elem...

Embodiment 3

[0052] Preparation of pyridine-bridged double ruthenium acetylene terminal compounds: under nitrogen protection, an appropriate amount of pentamethylcyclopentadienyl (1,2-bisdiphenylphosphineethane) ruthenium chloride Cp * Ru(dppe)Cl (preferably 500mg, 0.74mmol), 2,5-bis(trimethylsilylethynyl)pyridine (preferably 80mg, 0.30mmol) and potassium fluoride (preferably 205mg, 3.54mmol) were dissolved in an appropriate amount of methanol ( preferably 20ml) and tetrahydrofuran (preferably 3-4ml), the system is heated to reflux until the reaction is complete (about 24 hours), cooled to room temperature, suction filtered, and the solids are washed with 5-10ml methanol and 5-10ml n-hexane respectively , and then recrystallized with dichloromethane and n-hexane to obtain 289 mg of brown solid with a yield of 61%, and the structural formula of the double ruthenium acetylene terminal compound bridged by the gained pyridine is: Its NMR spectrum is shown in Figure 7-9 shown.

[0053] Elem...

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Abstract

The invention relates to the technical field of photoelectric materials, in particular to a pyridine-bridged ruthenium acetylene-terminated compound, which has a structural general formula shown in the specification, in the formula, Py is one of H or CH3, and R' is one of H, F, CH3, OCH3, CHO, COOEt and CN. According to the compound, pyridine and derivatives thereof are used as conjugated bridge chains, metal ruthenium is used as an oxidation-reduction active end group, and an electrochemical method test shows that the compound shows two continuous single-electron oxidation-reduction processes, shows good electron interaction (coupling), has the good charge transmission performance and has the good potential application prospects in the field of molecular wires.

Description

technical field [0001] The invention relates to the technical field of optoelectronic materials, in particular to a pyridine-bridged double ruthenium acetylene terminal compound and a preparation method and application thereof. Background technique [0002] Transition metal ruthenium end groups have been used to design metal-organic molecular wire materials due to their good redox reversibility and stability. Formally explore the electron transport ability of conjugated bridging ligands. [0003] As a class of aromatic heterocyclic organic molecules, pyridine and pyridine derivatives have good coordination ability and bonding properties. As auxiliary ligands, they have been used in the construction of metal-organic frameworks (MOFs) and pure organic compounds. frame material (COF), and apply it in gas adsorption, energy storage and other fields. [0004] If it is possible to synthesize a molecular wire material with good charge transport performance using pyridine and its ...

Claims

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Application Information

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IPC IPC(8): C07F17/02
CPCC07F17/02
Inventor 欧亚平庾江喜朱小明李俊华
Owner HENGYANG NORMAL UNIV
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