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Naphthalimide compound as well as preparation method and application thereof

A naphthalimide and compound technology, applied in the field of photochromic materials, can solve the problems of complex synthesis, fast light response speed, low total yield and the like, and achieve the effects of simple synthesis and low preparation cost

Active Publication Date: 2021-06-22
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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  • Naphthalimide compound as well as preparation method and application thereof
  • Naphthalimide compound as well as preparation method and application thereof
  • Naphthalimide compound as well as preparation method and application thereof

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-Naphthalenetetracarboxylic anhydride (1.41 g, 5.26 mmol) was dissolved in 50 mL of N,N-dimethylformamide, cyclohexylamine (0.52 g, 5.26 mmol)) and aniline (0.49 g, 5.26 mmol), heated to 150 °C for 24 h; the reaction solution was cooled to 20 °C, poured into 500 mL of water, filtered, and the filter cake was subjected to column chromatography (the stationary phase was silica gel, and dichloromethane was the mobile phase) to obtain the Naphthalimide compounds.

[0054] The hydrogen nuclear magnetic spectrum and carbon spectrum of the naphthalimide compounds are as follows figure 1 and figure 2 As shown, the specific chemical shifts are: 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=12.2, 3.7Hz, 1H), 2.54(qd, J=12.4, 3.5Hz, 2H)...

Embodiment 2

[0057] The present embodiment prepares a naphthalimide compound shown in the following structure:

[0058]

[0059] The preparation method is as follows:

[0060]

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

[0062] The hydrogen nuclear magnetic spectrum and carbon spectrum of the naphthalimide compounds are as follows image 3 and Figure 4 As shown, the specific chemical shifts are: 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), 2.63-2.41 (m, 2H), 1.87-1.70 (m, 4...

Embodiment 3

[0065] The present embodiment prepares a naphthalimide compound shown in the following structure:

[0066]

[0067] The preparation method is as follows:

[0068]

[0069] 1,4,5,8-Naphthalenetetracarboxylic anhydride (1.41 g, 5.26 mmol) was dissolved in 50 mL of ethanol, cyclohexylamine (0.52 g, 5.26 mmol)) and 3-aminopyridine (0.50 g, 5.26 mmol) were added , heated to 110°C for 48h; the reaction solution was cooled to 20°C, poured into 500 mL of water, filtered, and the filter cake was passed through column chromatography (the stationary phase was silica gel and chloroform was the mobile phase) to obtain the naphthalimides compound.

[0070] The hydrogen nuclear magnetic spectrum and carbon spectrum of the naphthalimide compounds are as follows Figure 5 and Image 6 As shown, the specific chemical shifts are: 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),2.47 -2.35(m, 2H), 1.92-1.74(m, 3H), 1.71(d, J=1...

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Abstract

The invention relates to a naphthalimide compound as well as a preparation method and application thereof, the structure of the naphthalimide compound is shown as a formula (I), and in the formula (I), R1 is selected from C4-8 chain alkyl and C5-7 cycloalkyl; and R2 is selected from phenyl and 5-7-membered aromatic heterocyclic radical. The naphthalimide compound provided by the invention is a naphthalimide compound with a novel structure, can generate a large number of free radicals under an illumination condition, and has a photochromic characteristic; and the compound is simple to synthesize and low in preparation cost, and can be widely applied to 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 Applications(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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