Bay organic phosphine bridging fiber perylene diimide containing phosphorus oxide bond structure and preparation method thereof

A technology of biperyleneimide and tetrabromoperyleneimide, applied in the field of organic chemical synthesis, can solve problems affecting device performance, poor solubility of peryleneimide and its derivatives, limitations of molecular synthesis and application research, etc. Achieve the effects of simple preparation reaction conditions, increased solubility and photothermal stability, and high yield

Inactive Publication Date: 2018-04-20
SOUTHWEAT UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the interaction between large π bonds leads to poor solubility of perylene imide and its derivatives. When used as organic acceptor photovoltaic materials and donor materials, the microphase separation formed by the materials will seriously affect The performance of the device, ultimately causing molecular synthesis and application research to be limited to a certain extent

Method used

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  • Bay organic phosphine bridging fiber perylene diimide containing phosphorus oxide bond structure and preparation method thereof
  • Bay organic phosphine bridging fiber perylene diimide containing phosphorus oxide bond structure and preparation method thereof
  • Bay organic phosphine bridging fiber perylene diimide containing phosphorus oxide bond structure and preparation method thereof

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preparation example Construction

[0024] Another aspect of the present invention provides a method for preparing a bay-position organophosphine-bridged peryleneimide containing a phosphorus-oxygen bond structure. In an exemplary embodiment of the preparation method of the b-position organic phosphine bridged perylene imide containing phosphorus-oxygen bond structure of the present invention, the preparation method may include:

[0025] Step S01, adding tetrabromoperylenetetracarboxylic dianhydride having the structure of formula (II) into the solvent, and adding primary amine compounds while stirring. After adding the primary amine compound, heat the reaction under an inert protective atmosphere, then cool to room temperature, remove the solvent and purify the obtained crude product to obtain a tetrabromoperyleneimide compound with a structure of formula (III), the reaction formula Can be:

[0026]

[0027] In this example, the primary amine compounds may include alkylamines, alkylamines containing substit...

example 1

[0058] (1) 1,6,7,12-tetrabromo-3,4,9,10-perylenetetracarboxylic dianhydride (1.4g, 2mmol) as the structure of formula (II) was added to 30mL of refined anhydrous To propionic acid, n-dodecylamine (1.1 g, 6 mmol) was added with stirring. Heated to 120°C for 12 hours under the protection of nitrogen, then cooled the reaction to room temperature, removed propionic acid by rotary evaporator, and purified the obtained crude product on a silica gel column (300-400 mesh) with a solution containing toluene as eluent 1.6 g of 1,6,7,12-tetrabromo-3,4,9,10-perylenetetracarboxylic diimide compound with the chemical structure shown in formula (III-1) was obtained with a yield of 76.7%. Mass spectral characterization data of the compound of formula (Ⅲ-1): ESI-MS (M+H) (m / z): 1043.1, calcd for C 48 h 55 Br 4 N 2 o 4 (m / z), 1042.1, Anal. Calcd for C 48 h 54 Br 4 N 2 o 4 .

[0059] (2) Add perylene imide (1.04g, 1.0mmol) of chemical structure shown in formula (Ⅲ-1) into 30mL of refi...

example 2

[0062] (1) Add 1,6,7,12-tetrabromo-3,4,9,10-perylenetetracarboxylic dianhydride (1.4g, 2mmol) of the structure of formula (II) into 30mL of refined toluene , added n-dodecylamine (1.1 g, 6 mmol) with stirring. Heated to 120°C for 12 hours under the protection of nitrogen, then cooled the reaction to room temperature, removed propionic acid by rotary evaporator, and purified the obtained crude product on a silica gel column (300-400 mesh) with a solution containing toluene as eluent 1.6 g of 1,6,7,12-tetrabromo-3,4,9,10-perylenetetracarboxylic diimide compound with the chemical structure shown in formula (III-1) was obtained with a yield of 76.7%. Mass spectral characterization data of the compound of formula (Ⅲ-1): ESI-MS (M+H) (m / z): 1043.1, calcd for C 48 h 55 Br 4 N 2 o 4 (m / z), 1042.1, Anal. Calcd for C 48 h 54 Br 4 N 2 o 4 .

[0063] (2) Add perylene imide (1.04g, 1.0mmol) with the chemical structure shown in formula (Ⅲ-1) into 30mL of refined anhydrous tetrahy...

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Abstract

The invention provides a bay organic phosphine bridging fiber perylene diimide containing a phosphorus oxide bond structure and a preparation method thereof. A structural formula of perylene diimide is described in the specification. The preparation method comprises the following steps: adding tetrabromo-perylene tertracarboxylic acid dianhydride into a solvent, stirring, adding a primary amine compound while stirring, heating for reaction in presence of inert gas, cooling, then removing the solvent, purifying to obtain a tetrabromo-perylene imine compound, then dissolving, carrying out water-free and oxygen-free treatment, cooling, then adding n-butyl lithium solution, carrying out reaction, then adding a compound containing methyl phosphonic dichloride, dissolving, washing, drying, and carrying out purification treatment, thus obtaining the bay organic phsophine bridging fiber perylene diimide containing the phosphorus oxide bond structure. The perylene diimide provided by the invention has relatively high solubility in the conventional organic solvent, the preparation method is simple, yield is high, and implementation is easy.

Description

technical field [0001] The invention belongs to the field of organic chemical synthesis, and more specifically relates to a bay-position organic phosphine bridged perylene imide with a phosphorus-oxygen bond structure and a preparation method thereof. Background technique [0002] As an important part of fluorescent materials, perylene imide derivatives have excellent photostability, adjustable spectral wavelength, large molar extinction coefficient, mostly single peaks at long wavelengths, simple structure synthesis, and easy modification of functional groups. Therefore, the synthesis, performance research and application of perylene imides have become a new research hotspot in the fields of chemistry, biology and physics. The number of perylene imides is large, the perylene nucleus has a large π-π conjugated electronic structure, and the π electron cloud has a high polarizability, and the interaction between the π electron clouds makes the π electrons form delocalization i...

Claims

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Application Information

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IPC IPC(8): C07F9/6564
CPCC07F9/6564
Inventor 马佳俊杨军校常冠军
Owner SOUTHWEAT UNIV OF SCI & TECH
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