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Bay-position organic phosphine bridged perylene bisimide containing phosphorus-sulfur bond structure and preparation method thereof

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

Inactive Publication Date: 2018-10-09
SOUTHWEAT UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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-position organic phosphine bridged perylene bisimide containing phosphorus-sulfur bond structure and preparation method thereof
  • Bay-position organic phosphine bridged perylene bisimide containing phosphorus-sulfur bond structure and preparation method thereof
  • Bay-position organic phosphine bridged perylene bisimide containing phosphorus-sulfur 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 bay-position organic phosphine bridged perylene imide with a phosphorus-sulfur bond structure. In an exemplary embodiment of the preparation method of the bay-position organic phosphine bridged perylene imide containing phosphorus-sulfur bond structure of the present invention, the preparation method may include:

[0025] Step S01, adding tetrabromoperylenetetracarboxylic dianhydride with the structure of formula (II) into the solvent, adding primary amine compounds under stirring conditions, heating the reaction under an inert protective atmosphere, and then cooling to room temperature, removing the solvent The obtained crude product is purified to obtain a tetrabromoperylene imide compound having the structure of formula (III). The reaction formula can be:

[0026]

[0027] In this example, the primary amine compound may include alkylamines, alkylamines containing substituents, cycloalkyls, cycloalkyls...

example 1

[0057] (1) Add 1,6,7,12-tetrabromo-3,4,9,10-perylenetetracarboxylic dianhydride (1.4g, 2mmol) with the structure of formula (II) to 30mL refined anhydrous In the propionic acid, add n-dodecylamine (1.1 g, 6 mmol) with stirring. Under the protection of nitrogen, the reaction was heated to 120°C for 12 hours, and then the reaction was cooled to room temperature. The propionic acid was removed by a rotary evaporator. The crude product obtained was purified by a silica gel column (300-400 mesh) with a solution containing toluene as the eluent , To obtain 1.6 g of 1,6,7,12-tetrabromo-3,4,9,10-perylenetetracarboxylic diimide compound with a chemical structure represented by formula (III-1), with a yield of 76.7%. Mass spectrometric characterization data of the compound of formula (Ⅲ-1): ESI-MS(M+H)(m / z):1043.1,calcd forC 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 .

[0058] (2) Add the perylene imide (1.04g, 1.0mmol) of the chemical structure represented b...

example 2

[0061] (1) Add 1,6,7,12-tetrabromo-3,4,9,10-perylenetetracarboxylic dianhydride (1.4g, 2mmol) with the structure of formula (II) to 30mL refined anhydrous In the propionic acid, add n-dodecylamine (1.1 g, 6 mmol) with stirring. Under the protection of nitrogen, the reaction was heated to 120°C for 12 hours, and then the reaction was cooled to room temperature. The propionic acid was removed by a rotary evaporator. The crude product obtained was purified by a silica gel column (300-400 mesh) with a solution containing toluene as the eluent , To obtain 1.6 g of 1,6,7,12-tetrabromo-3,4,9,10-perylenetetracarboxylic diimide compound with a chemical structure represented by formula (III-1), with a yield of 76.7%. Mass spectrometric 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 .

[0062] (2) Take the peryleneimide (1.04g, 1.0mmol) of the chemical structure represented ...

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Abstract

The invention provides bay-position organic phosphine bridged perylene bisimide containing phosphorus-sulfur bond structure and a preparation method thereof. The structural formula of perylene bisimide is as shown in the description. The preparation method comprises the following steps: adding tetrabromofluorene tetracarboxylic dianhydride into a solvent, adding primary amine compounds while stirring, heating in the presence of an inert gas, cooling, then removing a solvent, purifying to obtain a tetrabromophthalimide compound, dissolving, utilizing freeze-thaw degassing method, cooling, adding a solution of n-butyllithium, reacting, then adding a thiophosphoryl dichloride compound, and dissolving, washing, drying and purifying to obtain bay-position organic phosphine bridged perylene bisimide with phosphorus-sulfur bond structure. Perylene bisimide provided by the invention has greater solubility in a conventional organic solvent, and is simple in preparation, high in yield and easy to implement.

Description

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

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/6568C07D471/06C09K11/06
CPCC07F9/65681C07D471/06C07F9/65685C09K11/06C09K2211/1029C09K2211/1096
Inventor 马佳俊杨军校常冠军
Owner SOUTHWEAT UNIV OF SCI & TECH
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