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Bis(1,3-dithiol-2-carbonyl) fused naphthyl imide derivative and synthesis method thereof

A technology of naphthalenediimide and derivatives, applied in the field of naphthalenediimide derivatives and synthesis thereof, can solve the problems of consumption, occupation, unfavorable aromatic ring system functionalization and derivatization, etc., and achieves simple structure, The effect of simple synthesis route and simple structure

Inactive Publication Date: 2016-04-06
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] However, usually the introduction of sulfur heterocycles will consume and occupy the reaction sites in the original aromatic ring system while improving the performance of photoelectric materials, which is not conducive to the further functionalization and derivatization of the aromatic ring system [X.Gao, et al. , J.Am.Chem.Soc., 132, 3697 (2012)]

Method used

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  • Bis(1,3-dithiol-2-carbonyl) fused naphthyl imide derivative and synthesis method thereof
  • Bis(1,3-dithiol-2-carbonyl) fused naphthyl imide derivative and synthesis method thereof
  • Bis(1,3-dithiol-2-carbonyl) fused naphthyl imide derivative and synthesis method thereof

Examples

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Effect test

Embodiment 1

[0033] Add 2,3,6,7-tetrabromonaphthaloyl-n-butylimide (694mg, 1mmol) and N-methylimine potassium dithiocarbonate (1098mg, 6mmol) into a 100mL three-neck round bottom flask ; N 2 Under protection, add 50-60mL of anhydrous THF solvent to the above mixture, reflux and stir for 12h, and cool; transfer the cooled reaction mixture to a single-necked round-bottomed flask, and spin the solvent to dry under reduced pressure; Be 20mL mixed solvent that 1 / 5 joins in the reaction mixture that obtains, and at 90 o C stirred and reacted for 24 hours; the reaction mixture was filtered under reduced pressure, and the solid was washed with deionized water until the filtrate was neutral, and then washed three times with ethanol to obtain a purple-red filter cake; the obtained purple-red solid was dissolved in 30-40 mL of Add 2 to 3 g of silica gel to methyl chloride and mix well, spin the solvent under reduced pressure to obtain a purple solid powder; the purple solid powder is separated and p...

Embodiment 2

[0035] According to the method and steps described in Example 1, only 2,3,6,7-tetrabromonaphthalene diamide (750 mg, 1 mmol) was used instead of 2,3,6,7-tetrabromonaphthalene diamide n-Butylimine (694 mg, 1 mmol), 276 mg of orange-red solid powder was obtained, yield 45%. 1 HNMR (400MHz, CDCl 3 )δ(ppm):0.95-1.05(m,6H,-CH 3 ),1.40-1.56(m,12H,-CH 2 -),1.67-1.82(m,4H,-CH 2 -),4.25-4.35(m,2H,-CH 2 -N).

Embodiment 3

[0037] According to the method and steps described in Example 1, except that N-methylimine potassium dithiocarbonate (1464mg, 8mmol) was used instead of N-methylimine potassium dithiocarbonate (1098mg, 6mmol) to obtain an orange-red solid Powder 232mg, yield 42%. 1 HNMR (400MHz, CDCl 3 )δ(ppm):0.96-1.07(m,6H,-CH 3 ),1.41-1.52(m,4H,-CH 2 -),1.68-1.83(m,4H,-CH 2 -),4.23-4.36(m,2H,-CH 2 -N).

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Abstract

The invention relates to a bis(1,3-dithiol-2-carbonyl) fused naphthyl imide derivative and a synthesis method thereof, in particular to a method for synthesizing a bis(1,3-dithiol-2-carbonyl) fused naphthyl imide intermediate by performing nucleophilic substitution on halogenated naphthyl imide and carrying out imine hydrolysis under the circumstance that 2,3,6,7-naphthyl imide is taken as a raw material and N-methyl imine dithiocarbonic acid alkali metal salt as a sulfurizing agent. The bis(1,3-dithiol-2-carbonyl) fused naphthyl imide derivative is a kind of an important organic photoelectric material intermediate; according to the synthesis method of the bis(1,3-dithiol-2-carbonyl) fused naphthyl imide derivative, transition metal catalysis, high temperature, water absence, oxygen absence and other severe conditions required for the conventional sulfur atom introduction method are avoided; not only is an intermediate which is simple in structure and easy to derive provided, but also a novel method for conveniently synthesizing bis(1,3-dithiol-2-carbonyl) fused naphthyl imide in a relatively large scale is provided.

Description

technical field [0001] The present invention relates to a kind of bis(1,3-dithio-2-carbonyl) fused naphthalene diimide derivative and its synthesis method, especially in N-methyl imine dithiocarbonate alkali metal salt As a sulfidation reagent, the halogenated naphthalene diimide is subjected to nucleophilic substitution, and the synthesis method of bis(1,3-dithio-2-carbonyl) fused naphthalene diimide intermediate is obtained by imine hydrolysis. Background technique [0002] Organic photoelectric materials containing large aromatic ring conjugated structures have unparalleled advantages over traditional inorganic materials such as diverse structures, low cost, easy processing, light weight, and large-area production. They are widely used in light-emitting diodes, field-effect transistors, thermal batteries, Solar cells and other fields have a wide range of applications. One of the important factors determining the performance of organic optoelectronic devices is the carrie...

Claims

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Application Information

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IPC IPC(8): C07D495/22
CPCC07D495/22
Inventor 陈光明高彩艳
Owner INST OF CHEM CHINESE ACAD OF SCI
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