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Synthesis method of 3,6-halogen atom-substituted 1,8-naphthalimide

A technology of naphthalimide and synthesis method, applied in the direction of organic chemistry, etc., can solve the problems of difficult separation and purification, harsh preparation conditions, etc., and achieve the effect of simple separation and purification and mild reaction conditions

Active Publication Date: 2017-05-31
NANCHANG UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the literature, it is prepared by direct bromination of 1,8-naphthalene dicarboxylic anhydride (Tetrahedron Letters 2013, 54, 4963–4965), which has the disadvantages of harsh preparation conditions and difficult separation and purification

Method used

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  • Synthesis method of 3,6-halogen atom-substituted 1,8-naphthalimide
  • Synthesis method of 3,6-halogen atom-substituted 1,8-naphthalimide
  • Synthesis method of 3,6-halogen atom-substituted 1,8-naphthalimide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Example 1: 3,6-dibromo-N-(2-octyldodecyl)-1,8-naphthalimide (B 1 )

[0017]

[0018] In a 50mL flask, add reactant A (0.102g, 0.20mmol), 7mL 42% hydrobromic acid aqueous solution, stir it with a magnetic stirrer to fully form a salt, and then slowly add 0.110g dissolved in 4mL water in an ice-salt bath (1.59mmol)NaNO 2 After dripping, stir under ice-salt bath for 0.5h, then slowly add 0.110g (0.77mmol) CuBr solution dissolved in 6mL of 42% hydrobromic acid aqueous solution, stir and react until the solution is clear or stir overnight, react After stopping, it was extracted with dichloromethane, washed with water, dried with anhydrous magnesium sulfate, filtered, and separated by column to obtain 0.058 g of light yellow solid with a yield of 45.4%. 1 HNMR (300MHz, CDCl 3 )δ H :8.63(s,2H),8.26(s,2H),4.07(d,2H),1.22-1.29(m,33H),0.85-0.87(m,6H); HRMS: Calcd for C 32 h 45 Br 2 NO 2 633.1817, found: 633.1836 (M - , MALDI-TOF).

Embodiment 2

[0019] Example 2: 3,6-diiodo-N-(2-octyldodecyl)-1,8-naphthalimide (C 1 )

[0020]

[0021] In a 50mL flask, add reactant A (0.102g, 0.20mmol), 7mL of 37% hydrochloric acid aqueous solution, stir it with a magnetic stirrer to make it fully salt, then slowly add dropwise 0.110g (1.59 mmol)NaNO 2 After dripping, stir in an ice-salt bath for 0.5h, then slowly add 0.30g (1.81mmol) KI solution dissolved in 5mL of water dropwise, stir until the solution is clear or stir overnight, and extract with dichloromethane after the reaction stops , washed with water, dried with anhydrous magnesium sulfate, filtered, and column separated to obtain 0.060 g of a dark red solid with a yield of 41.2%. 1 HNMR (300MHz, CDCl 3 )δ H :8.78(s,2H),8.45(s,2H),4.07(d,2H),1.22-1.29(m,33H),0.85-0.87(m,6H); HRMS: Calcd forC 32 h 45 I 2 NO 2 729.1540, found: 729.1522 (M - , MALDI-TOF).

Embodiment 3

[0022] Example 3: 3,6-dibromo-N-(2-octyldodecyl)-1,8-naphthalimide (B 1 )

[0023]

[0024]In a 50mL flask, add reactant A (0.102g, 0.2mmol), 7mL 42% hydrobromic acid aqueous solution, add 7mL water and stir it with a magnetic stirrer to fully form a salt, then add 7mL THF, and then Slowly add 0.110g (1.59mmol) NaNO dissolved in 4mL of water dropwise 2 After dripping, stir under ice-salt bath for 0.5h, then slowly add 0.110g (0.77mmol) CuBr solution dissolved in 6mL of 42% hydrobromic acid aqueous solution, stir and react until the solution is clear or stir overnight, react After stopping, it was extracted with dichloromethane, washed with water, dried with anhydrous magnesium sulfate, filtered, and separated by column to obtain 0.051 g of a light yellow solid with a yield of 40%. 1 HNMR (300MHz, CDCl 3 )δ H :8.63(s,2H),8.26(s,2H),4.07(d,2H),1.22-1.29(m,33H),0.85-0.87(m,6H); HRMS: Calcd for C 32 h 45 Br 2 NO 2 633.1817, found: 633.1836 (M - , MALDI-TOF).

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Abstract

The invention discloses a synthesis method of 3,6-halogen atom-substituted 1,8-naphthalimide. The synthesis method comprises the following steps of introducing halogen atoms to 3 and 6 bits of 1,8-naphthalimide; taking 3,6-diamido-1,8-naphthalimide, sodium nitrite and cuprous halide as raw materials, wherein the molar ratio of the 3,6-diamido-1,8-naphthalimide to the sodium nitrite is 1:(1-10), and the molar ratio of the 3,6-diamido-1,8-naphthalimide to the cuprous halide is (1:1) to (1:10); and reacting for 1-48h at a low temperature of -10 DEG C to 10 DEG C under a mixed solvent to obtain the 3,6-halogen atom-substituted 1,8-naphthalimide. The 3,6-halogen atom-substituted 1,8-naphthalimide is greatly prepared through mild conditions. The method has the advantages of being simple and convenient to separate and purify and mild in reaction conditions.

Description

technical field [0001] The invention belongs to the field of organic chemical industry and fine chemical industry, and specifically relates to a method for synthesizing 1,8-naphthalimide substituted by 3,6 halogen atoms. Background technique [0002] 1,8-Naphthimide is a new type of organic semiconductor unit used in the construction of organic semiconductor materials, and has been successfully used in the field of solar cells (ACS Appl.Mater.Interfaces 2016,8,5475-5483), showing Excellent device performance. [0003] 1,8-naphthoimides substituted with 3,6 halogen atoms are an important class of organic semiconductor intermediates, which can be used to construct high-performance organic semiconductor materials. In the literature, the direct bromination method of 1,8-naphthalene dicarboxylic anhydride (Tetrahedron Letters 2013, 54, 4963–4965) has the disadvantages of harsh preparation conditions and difficult separation and purification. Contents of the invention [0004]...

Claims

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Application Information

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IPC IPC(8): C07D221/14
CPCC07D221/14
Inventor 袁忠义朱国民廉小翠胡昱陈义旺
Owner NANCHANG UNIV
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