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A kind of naphthalimide compound and its preparation method and application

A naphthalimide and compound technology, applied in the field of photochromic materials, can solve the problems of fast photoresponse, complex synthesis, low total yield, etc., and achieve the effect of low preparation cost and simple synthesis

Active Publication Date: 2022-04-05
PINGXIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The sulfuryl fluoride atmosphere is used in the synthesis process of this type of material, which has very high raw material cost and process cost, and it is difficult to achieve large-scale application
[0005] CN111808120A discloses a spirooxazine photochromic compound from colorless to blue and its preparation method and application. The spirooxazine photochromic compound from colorless to blue prepared by the invention not only has light response speed Fast, at the same time, fades quickly, and the closed-loop state has stable performance when used outdoors, does not contain precious metals, but the activity of nanozymes is low, and the antibacterial performance is weak
And the synthesis is complicated, requiring 4-5 steps of organic reaction, the total yield is not high, and the price of raw materials is high

Method used

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  • A kind of naphthalimide compound and its preparation method and application
  • A kind of naphthalimide compound and its preparation method and application
  • A kind of naphthalimide compound and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] This embodiment prepares a kind of naphthalimide compound shown in the following structure:

[0050]

[0051] The preparation method is as follows:

[0052]

[0053]1,4,5,8-naphthalene tetracarboxylic anhydride (1.41g, 5.26mmol) was dissolved in 50mL N,N-dimethylformamide, cyclohexylamine (0.52g, 5.26mmol)) and aniline (0.49 g, 5.26mmol), heated to 150°C and kept at a constant temperature for 24h; after the reaction solution was cooled to 20°C, it was poured into 500mL of water, filtered, and the filter cake was passed through column chromatography (stationary phase was silica gel, dichloromethane was used as mobile phase) to obtain the described Naphthalimide compounds.

[0054] The proton nuclear magnetic spectrum and the carbon spectrum of this naphthalimide compound are as follows respectively figure 1 and figure 2 Shown, the specific chemical shift is: 1 H NMR (400MHz, CDCl 3 )δ=8.82-8.75(m,4H),7.62-7.56(m,2H),7.56-7.50(m,1H),7.36-7.31(m,2H),5.04(tt,J=1...

Embodiment 2

[0057] This embodiment prepares a kind of naphthalimide compound shown in the following structure:

[0058]

[0059] The preparation method is as follows:

[0060]

[0061] Dissolve 1,4,5,8-naphthalene tetracarboxylic anhydride (1.41 g, 5.26 mmol) in 50 mL of N,N-dimethylformamide, add cyclohexylamine (0.52 g, 5.26 mmol)) and 4-amino Pyridine (0.50g, 5.26mmol), heated to 130°C and kept at a constant temperature for 36h; after the reaction solution was cooled to 20°C, poured into 500mL of water, filtered, and the filter cake was passed through column chromatography (stationary phase was silica gel, chloroform was used as mobile phase), The naphthalimide compound is obtained.

[0062] The proton nuclear magnetic spectrum and the carbon spectrum of this naphthalimide compound are as follows respectively image 3 and Figure 4 Shown, the specific chemical shift is: 1 H NMR (400MHz, CDCl 3 )δ=8.87(d,J=6.3Hz,2H),8.83-8.76(m,4H),7.40(d,J=5.8Hz,2H),5.03(tt,J=12.3,3.7Hz,1H),...

Embodiment 3

[0065] This embodiment prepares a kind of naphthalimide compound shown in the following structure:

[0066]

[0067] The preparation method is as follows:

[0068]

[0069] Dissolve 1,4,5,8-naphthalene tetracarboxylic anhydride (1.41 g, 5.26 mmol) in 50 mL of ethanol, add cyclohexylamine (0.52 g, 5.26 mmol)) and 3-aminopyridine (0.50 g, 5.26 mmol) , heated to 110°C and kept at a constant temperature for 48h; after the reaction solution was cooled to 20°C, it was poured into 500mL of water, filtered, and the filter cake was passed through column chromatography (stationary phase was silica gel, and chloroform was used as mobile phase) to obtain the naphthalimides compound.

[0070] The proton nuclear magnetic spectrum and the carbon spectrum of this naphthalimide compound are as follows respectively Figure 5 and Figure 6 Shown, the specific chemical shift is: 1 H NMR (400MHz, DMSO-d 6 )δ8.84-8.53(m,7H),7.94(dt,J=8.1,1.7Hz,2H),7.64(dd,J=8.0,4.8Hz,1H),5.00-4.79(m,1H),...

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Abstract

The present invention relates to naphthalimide compound and its preparation method and application, the structure of described naphthalimide compound is shown in formula (I), wherein, R 1 from C 4‑8 Alkanes, C 5‑7 Cycloalkyl; R 2 Selected from phenyl, 5-7 membered aromatic heterocyclic groups. The naphthalimide compound involved in the present invention is a novel structure naphthalimide compound, which can generate a large amount of free radicals under light conditions and has photochromic properties; and its synthesis is simple, and the preparation cost is low. It can be widely used in the preparation of photochromic materials.

Description

technical field [0001] The invention belongs to the technical field of photochromic materials, and relates to a naphthalimide compound and its preparation method and application, in particular to a naphthalimide compound, its preparation method and photochromic compounds with simple synthesis and low cost. Applications in chromogenic materials. Background technique [0002] Compared with inorganic photochromic materials, organic photochromic materials have been widely studied due to their fast response and easy processing, and have been applied in the fields of photochromic lenses, optical information recording materials, molecular wires and molecular switches. [0003] The discoloration mechanism of organic photochromic materials has the following two types: 1. Certain changes in organic molecular structure (chemical bond dissociation, heterogeneous cleavage / photocyclization, cis-trans isomerization, protonation or deprotonation processes, etc.); 2. Redox active organic mo...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/06C09K9/02
CPCC07D471/06C09K9/02C09K2211/1044C09K2211/1029
Inventor 廖建珍柯华
Owner PINGXIANG UNIV
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