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Phenyl-bridged triarylamine and ferrocene end group compound, preparation method and application thereof

A technology of monobrominated phenylferrocene and phenyl bridges, applied in the direction of iron organic compounds, etc., can solve problems such as unseen

Active Publication Date: 2019-01-18
HENGYANG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

If the organic-inorganic hybrid molecular wire model can be combined with ferrocene and triarylamine as redox-active end group conjugated bridges, it will provide another new way for the design and synthesis of new molecular wires, which is regrettable. Yes, haven't seen any reports about it yet

Method used

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  • Phenyl-bridged triarylamine and ferrocene end group compound, preparation method and application thereof
  • Phenyl-bridged triarylamine and ferrocene end group compound, preparation method and application thereof
  • Phenyl-bridged triarylamine and ferrocene end group compound, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Preparation of phenyl-bridged triarylamine and ferrocene end-group compounds: add 0.2 g (0.464 mmol) of borate-substituted triarylamine and 0.143 g (0.420 mmol) of monobromophenylferrocene to a round-bottomed flask , 2 mL of potassium carbonate solution with a concentration of 2 mol / L, 2 mL of ethanol and 10 mL of toluene, the mixed system was stirred and heated to reflux for 24 h, cooled, and the mixed system was mixed with CH 2 Cl 2 solvent extraction, the obtained organic phase was washed with saturated NaCl solution, and then washed with anhydrous NaCl 2 SO 4 Dry, filter, spin the filtrate with a rotary evaporator at a pressure of 0.01 Kpa and a temperature of 30°C, and separate by column chromatography (eluent: ethyl acetate / petroleum ether (V / V = 1:8) to obtain Orange-red solid 182 mg, yield: 77%.

[0030] .

[0031] Elemental analysis (C 36 h 31 FeNO 2 ): theoretical value: C, 76.46; H, 5.53. Found: C, 76.55; H, 5.38.

[0032] Structural data: 1 H NMR...

Embodiment 2

[0035] Preparation of phenyl-bridged triarylamine and ferrocene end-group compounds: add 0.2 g (0.464 mmol) of borate-substituted triarylamine and 0.143 g (0.420 mmol) of monobromophenylferrocene to a round-bottomed flask , 2 mL of potassium carbonate solution with a concentration of 2 mol / L, 2 mL of ethanol and 10 mL of toluene, the mixed system was stirred and heated to reflux for 24 h, cooled, and the mixed system was mixed with CH 2 Cl 2 solvent extraction, the obtained organic phase was washed with saturated NaCl solution, and then washed with anhydrous NaCl 2 SO 4 Dry, filter, spin the filtrate with a rotary evaporator at a pressure of 0.01 Kpa and a temperature of 30°C, and separate by column chromatography (eluent: ethyl acetate / petroleum ether (V / V = 1:8) to obtain Orange-red solid 160 mg, yield: 67%.

[0036]

[0037] Elemental analysis (C 36 h 31 FeNO 2 ): theoretical value: C, 76.46; H, 5.53. Found: C, 76.41; H, 5.60.

[0038] Structural data: 1 H NMR (...

Embodiment 3

[0041] Preparation of phenyl-bridged triarylamine and ferrocene end-group compounds: add 0.4 g (0.928 mmol) of borate-substituted triarylamine and 0.286 g (0.840 mmol) of monobromophenylferrocene to a round-bottomed flask , 5 mL of potassium carbonate solution with a concentration of 2 mol / L, 5 mL of ethanol and 20 mL of toluene, the mixed system was stirred and heated to reflux for 24 h, cooled, and the mixed system was mixed with CH 2 Cl 2 solvent extraction, the obtained organic phase was washed with saturated NaCl solution, and then washed with anhydrous NaCl 2 SO 4 Dry, filter, spin the filtrate with a rotary evaporator at a pressure of 0.01 Kpa and a temperature of 30°C, and separate by column chromatography (eluent: ethyl acetate / petroleum ether (V / V = 1:8) to obtain Orange-red solid 266 mg, yield: 56%.

[0042] .

[0043] Elemental analysis (C 36 h 31 FeNO 2 ): theoretical value: C, 76.46; H, 5.53. Found: C, 76.39; H, 5.62.

[0044] Structural data: 1 H NMR...

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Abstract

The invention discloses a phenyl-bridged compound with triarylamine and ferrocene end groups, a method for preparing the phenyl-bridged compound and application thereof, and relates to the technical field of photoelectric materials. A structural formula of the phenyl-bridged compound with the triarylamine and ferrocene end groups is shown. An R in the structural formula represents H or CH3 or OCH3; intermediate benzene ring joints are positioned at meta-positions or para-positions of respective benzene rings. The phenyl-bridged compound with the triarylamine and ferrocene end groups, the method and the application have the advantages that the phenyl-bridged compound is of a novel molecular structure, strong electron interaction between the end groups of the phenyl-bridged compound is discovered via tests by the aid of electrochemical processes, accordingly, novel molecular conducting wire materials can be developed on the basis of the phenyl-bridged compound, and a novel way for designing and synthesizing novel molecular conducting wires in follow-up procedures can be developed by the phenyl-bridged compound with the novel structure.

Description

technical field [0001] The invention relates to the technical field of photoelectric materials, in particular to a phenyl-bridged triarylamine and a ferrocene end group compound, a preparation method and application thereof. Background technique [0002] Ferrocene is a metallocene compound, which can form metal organic compounds with organic conjugated molecules, such as ferrocene acetylene compounds. 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] It can be known from published literature that both ferrocene and triarylamine have excellent electrochemical activity and stability. In recent years, there have been quite a number of documents disclosing the synthesis method of bis-ferrocene or bis-tri...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F15/02
CPCC07F15/02
Inventor 欧亚平
Owner HENGYANG NORMAL UNIV
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