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Preparation and application of thienyl-containing pyrazolone derivatives and their polymer films

A thienyl pyrazolone and polymer film technology is applied in the field of preparation and application of thienyl pyrazolone derivatives and polymer films thereof, and can solve the problems of inconvenient popularization and application of solid powder crystals, fatigue resistance, The thermal stability of photosensitivity cannot meet the problems of practical application, and achieves the effects of good photochromic performance, high sensitivity and simple method.

Inactive Publication Date: 2016-07-06
XINJIANG UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the fatigue resistance, photosensitivity, and thermal stability of the previously synthesized pyrazolone compounds still cannot meet the requirements of practical applications, and the solid powder crystals are not convenient for practical application.

Method used

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  • Preparation and application of thienyl-containing pyrazolone derivatives and their polymer films
  • Preparation and application of thienyl-containing pyrazolone derivatives and their polymer films
  • Preparation and application of thienyl-containing pyrazolone derivatives and their polymer films

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Example 1: Preparation of 1-phenyl-3-thiophene-4-thiophene methylene-5-hydroxypyrazolone phenylsemicarbazide [PD(2 -Th)P-PSC]

[0018] Weigh 1.7627g (5.0mmol) 1-phenyl-3-thiophene-4-thienoyl-5-hydroxypyrazolone [PD(2-Th)P-PSC] and 0.7563g (5.0mmol) phenyl Put semicarbazide (PSC) in a round-bottomed flask, use 5mL ethanol as solvent, 5-7 drops of glacial acetic acid as catalyst, heat to 80°C with magnetic stirring and reflux for 2h, filter with suction, recrystallize, and dry to obtain 2.1368g of white product ( 4.4mmol), yield 88%, melting point: 209.1-210.0°C. The white powder turns yellow after being irradiated with 365nm ultraviolet light; the yellow powder turns from yellow to white after being irradiated with visible light.

[0019] The synthetic route and photochromic mechanism of this type of compound are as follows: figure 1 shown.

Embodiment 2

[0020] Example 2: Preparation of PD(2-Th)P-PSC / PS composite film by method one

[0021] At room temperature, under the condition of magnetic stirring, slowly add 0.25g polystyrene (PS) into 2mL toluene, stir continuously to fully dissolve PS, and form a clear solution. Then, under the condition of avoiding light, 0.02 g of PD(2-Th)P-PSC white powder was slowly added into the clear solution, superceded in the ultrasonic instrument for 5 minutes, and continued to stir for 10 minutes to make PD(2-Th)P-PSC The PSC dispersed well into the clear solution, resulting in a co-suspension. After defoaming by standing in the dark, slowly pour the blended suspension into a clean Petri dish. The PD(2-Th)P-PSC / PS composite polymer film was obtained by natural air-drying at room temperature for 24 hours in the dark, and the content of PD(2-Th)P-PSC was 8wt%. The film has good photochromic properties.

[0022] The optical photographs of PD(2-Th)P-PSC / PS composite films are as follows figu...

Embodiment 3

[0023] Example 3: Preparation of PD(2-Th)P-PSC / PS Composite Film by Method 2

[0024] Use an ordinary square glass sheet (20mm×20mm×2mm) as the substrate, clean and dry it before use. Fix the substrate on a spin coater, drop the blended suspension of PD(2-Th)P-PSC and PS prepared in Example 2 onto the substrate, rotate at a certain speed for 30s, and spin coat The solution was evenly spread into a thin film, and placed in the dark at room temperature to dry naturally to obtain a PD(2-Th)P-PSC / PS composite film with a PD(2-Th)P-PSC content of 8wt%. This film also has photochromic properties.

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Abstract

The invention belongs to an organic photochromic material, and relates to preparations and applications of a thienyl group-containing pyrazolone derivative and its polymer film. The thienyl group-containing pyrazolone derivative is anyone of 1-phenyl-3-substituted-phenyl / thienyl / pyrryl / furyl / pyridyl / naphthyl-4-thienylmethylene-5-hydroxypyrazolone phenylsemicarbazone / methylthiosemicarbazide / ethylthiosemicarbazide / thiosemicarbazide or 1-phenyl-3-thienyl-4-subsituted-phenylmethylene / thienylmethylene / pyrrylmethyl / furylmethylene / pyridylmethylene / naphthylmethylene-5-hydroxypyrazolone phenylsemicarbazone / methylthiosemicarbazide / ethylthiosemicarbazide / thiosemicarbazide, and the polymer is anyone of polystyrene, polymethylstyrene, polyethylene and polypropylene. The thienyl group-containing pyrazolone derivative and its polymer film can be used in the information storage field, the molecular switch field, the false proof field, the optical eyeglass field, the intelligent window field and the like.

Description

technical field [0001] The invention belongs to the field of organic photochromic materials, in particular to the preparation and application of thienyl-containing pyrazolone derivatives and polymer films thereof. Background technique [0002] Photochromic material refers to that when it is irradiated by light of a certain wavelength, it can carry out a specific chemical reaction, and its absorption spectrum changes due to the change of structure, and it can also change its absorption spectrum under the irradiation of light of another wavelength or under the action of heat. A new type of functional material that returns to its original form. Photochromic materials include both inorganic and organic. Inorganic photochromic materials mainly include metal halides and metal oxides. Organic photochromic materials include spiro rings, diarylethenes, salicylaldehyde aniline derivatives, stilbene derivatives, dyes, o-nitrobenzyl derivatives, and the like. Due to the potential app...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D409/04C07D409/14C07D409/06C09K9/02C08L25/06C08L25/16C08L23/06C08L23/12C08K5/45
Inventor 刘浪孙虎斌贾殿赠
Owner XINJIANG UNIVERSITY
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