Diimide derivative containing isothioindene and preparation method thereof

A technology of imide and derivative is applied in the field of isothianaline-containing imide derivative and preparation thereof, can solve problems such as difficulty in synthesis, achieve low cost of raw materials, lower LUMO energy level, and large conjugation system effect

Pending Publication Date: 2022-07-12
WUHAN INSTITUTE OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are difficulties in its synthesis. The present invention discloses a new type of imide derivative containing isothioindene and its preparation method

Method used

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  • Diimide derivative containing isothioindene and preparation method thereof
  • Diimide derivative containing isothioindene and preparation method thereof
  • Diimide derivative containing isothioindene and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] A kind of imide derivative containing isothiane, the concrete preparation method is as follows:

[0054] (1) Put 1 g of compound 1 (6.57 mmol) into a dry three-necked flask, evacuate for 10-15 minutes, add 100 mL of dry tetrahydrofuran with a syringe, transfer it into a -78°C ethanol ice bath, and stir for 15 min to obtain a uniform solution, 2.75 g of bis(trimethylsilyl) lithium amide (16.42 mmol) was added dropwise to the solution with a syringe, the temperature was slowly raised to 25 °C, stirred for 3 h, and deoxygenated to obtain compound 2. Compound 2 did not need to be purified. used for the next reaction.

[0055] The reaction formula is as follows:

[0056]

[0057] (2) 600mg of compound 2 (4.47mmol) was dissolved in 100mL of tetrahydrofuran, transferred to -78°C ethanol ice bath, and 1.30g of N,N,N',N'-tetramethylethylenediamine (11.18mmol) was added with a syringe , stirred for 15 min, then added 4.11 mL of n-butyllithium (10.28 mmol) dropwise with a syr...

Embodiment 2

[0076] A kind of imide derivative containing isothiane, the concrete preparation method is as follows:

[0077] (1) 500mg of compound 1 (1.09mmol), 1.19g of compound 2 (2.72mmol) and 62.83mg of tetrakis(triphenylphosphine)palladium (0.109mmol) were added to the reaction tube successively, protected from light, and evacuated for 10-15min , and then 20 mL of toluene was added to the reaction tube with a syringe, the temperature was raised to 110 ° C and the reaction was performed overnight, the product was extracted three times with dichloromethane, the organic phases were combined, dried with anhydrous sodium sulfate, and the solvent was removed by rotary evaporation. A mixture of petroleum ether (dichloromethane and petroleum ether in a volume ratio of 1:2) was used as the eluent to carry out silica gel column chromatography separation to obtain product 3 in a yield of 25%.

[0078] The reaction formula is as follows:

[0079]

[0080] (2) Dissolve 2.66g of potassium hydro...

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Abstract

The invention relates to an isoindane-containing diimide derivative and a preparation method thereof. The structural formula of the isoindane-containing diimide derivative is shown in the specification, r and R'are respectively and independently selected from alkyl, alkoxy and alkyl or alkoxy substituted aryl, the alkyl in the alkyl or alkoxy is selected from one of straight-chain or branched-chain alkyl with the carbon atom number of 1-30, and n is an integer between 1 and 5. The isothioindene-containing diimide derivative provided by the invention has good solubility and relatively high electron affinity, and has great application potential in the fields of organic semiconductors, organic magnets and the like.

Description

technical field [0001] The invention belongs to the technical field of heterocyclic compounds, and relates to an isothianaphthene-containing imide derivative and a preparation method thereof. Background technique [0002] Imide-based materials are a class of materials that are widely used in bioimaging, organic optoelectronics, organic magnets, and other fields. Therefore, new imide-based materials need to be developed. These novel diimide-based materials are usually based on aromatic rings and their fused ring compounds, including fused ring compounds of benzene rings, as well as nitrogen-doped six-membered rings, thiophene rings, and the like. Different from general aromatic rings and their condensed ring compounds, isothianaphthenes tend to form quinoid configuration, which has a great influence on material properties. The introduction of sulfur atoms can lower its LUMO energy level and achieve effective electron orbital overlap. In addition to this, isothianaphthene ha...

Claims

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Application Information

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IPC IPC(8): C07D495/16H01L51/30
CPCC07D495/16H10K85/657H10K10/46Y02E10/549
Inventor 高翔
Owner WUHAN INSTITUTE OF TECHNOLOGY
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