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Aromatic ring bridged ferrocene and diphenylamine compound and preparation method and application thereof

A technology of compound and diphenylamine, which is applied in the field of ferrocene and diphenylamine compounds and their preparation, can solve the problems of high cost, defective preparation method, unfavorable production and use, etc., and achieve high synthesis rate, strong electronic interaction, charge Strong delocalization effect

Pending Publication Date: 2021-06-08
HENGYANG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, this strategy requires the use of expensive ferroceneboronic acid raw materials and corresponding metal palladium catalysts, which is costly and unfavorable for production and use.
[0003] It can be seen that the above-mentioned existing ferrocene and triarylamine are connected by a C-C single bond. There are defects in the preparation method, and it is urgent to be further improved.

Method used

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  • Aromatic ring bridged ferrocene and diphenylamine compound and preparation method and application thereof
  • Aromatic ring bridged ferrocene and diphenylamine compound and preparation method and application thereof
  • Aromatic ring bridged ferrocene and diphenylamine compound and preparation method and application thereof

Examples

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Embodiment 1

[0037] In this embodiment, p-nitroaniline I-1a and ferrocene are raw materials, and R is OCH 3 As a specific example, the synthesis of aromatic ring bridged ferrocene and diphenylamine compounds is carried out. Concrete synthetic steps are:

[0038] The first step: the synthesis of intermediate I-1b

[0039] Take 14 g (0.1mol) of raw material I-1a, add 30ml of water and 30ml of concentrated sulfuric acid in sequence, heat to dissolve them all, cool to 5°C in an ice-water bath, and gradually add 7g of NaNO 2 20ml aqueous solution, stirred for 1h, added urea to decompose excess HNO 2 , the resulting yellow diazonium salt solution is set aside.

[0040] Take 9.5g (0.05mol) of raw material ferrocene and dissolve it in 100ml of ether, add 1g of hexadecyltrimethylammonium bromide, stir for 1-2h, add it dropwise to the above diazonium salt solution, after the addition, put it under room temperature After reacting for 0.5h, ether was evaporated, filtered and washed with water. Th...

Embodiment 2

[0054] In this embodiment, m-nitroaniline I-2a and ferrocene are raw materials, and R is OCH 3 As a specific example, the synthesis of aromatic ring bridged ferrocene and diphenylamine compounds is carried out. Concrete synthetic steps are:

[0055] The first step: the synthesis of intermediate I-2b

[0056] Take 14 g (0.1 mol) of raw material I-2a, add 30ml of water and 30ml of concentrated sulfuric acid in sequence, heat to dissolve them all, cool to 5°C in an ice-water bath, and gradually add 7g of NaNO dropwise with a constant pressure dropping funnel 2 20ml aqueous solution, stirred for 1h, added urea to decompose excess HNO 2 , the resulting yellow diazonium salt solution is set aside.

[0057] Dissolve 9.5g (0.05mol) of raw material ferrocene in 100ml of ether, add 1g of hexadecyltrimethylammonium bromide, stir for 1-2h, add dropwise to the above diazonium salt solution, after the addition, put After reacting for 0.5h, ether was evaporated, filtered and washed with ...

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Abstract

The invention discloses an aromatic ring bridged ferrocene and diphenylamine compound ands a preparation method and application thereof, and belongs to the technical field of photoelectric materials. According to the preparation method of the aromatic ring bridged ferrocene and diphenylamine compound, ferrocene and an amino nitro substituted aromatic ring are taken as starting raw materials, and the aromatic ring bridged ferrocene and diphenylamine compound is constructed without participation of noble metal. The aromatic ring bridged ferrocene and diphenylamine compound has an electron coupling effect, a new research thought is provided for synthesis of a novel molecular wire, and the preparation method has the advantages of cheap raw materials, high synthesis rate and great reduction of the production cost.

Description

technical field [0001] The invention relates to the technical field of photoelectric materials, in particular to aromatic ring bridged ferrocene and diphenylamine compounds and their preparation methods and applications. Background technique [0002] Inorganic-organic hetero-redox-active end-group molecular wires have been applied to study intramolecular charge transfer, and it is expected to explore molecular wires with excellent performance, which mainly uses simple electrochemical techniques to explore the electrons between two redox-active end groups. Interaction, so as to judge the charge transport ability of the intermediate bridge chain. Ferrocene and organic triarylamine, as the classic inorganic and organic redox active terminal groups, have been widely used to construct homonuclear and heteronuclear molecular wire models. It is also reported in the literature that ferrocene and triarylamine are connected through a C-C single bond to explore their electronic coupli...

Claims

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Application Information

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IPC IPC(8): C07F17/02
CPCC07F17/02
Inventor 欧亚平张倩庾江喜朱小明张复兴
Owner HENGYANG NORMAL UNIV