Photochromic thiophene-thiazole heterocycle hybrid asymmetric perfluorocyclopentene compound, preparation method and application

A perfluorocyclopentene, photochromic technology, applied in chemical instruments and methods, color-changing fluorescent materials, organic chemistry, etc., can solve the problem that the use has not yet been reported, and achieve good photochromic performance and significant fatigue resistance. , the effect of good chemical and thermal stability

Inactive Publication Date: 2009-12-02
JIANGXI SCI & TECH NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, thiophene and 2-substituted thiazole heterocyclic mixed-type perfluorocyclopentene compounds and their uses have not been reported

Method used

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  • Photochromic thiophene-thiazole heterocycle hybrid asymmetric perfluorocyclopentene compound, preparation method and application
  • Photochromic thiophene-thiazole heterocycle hybrid asymmetric perfluorocyclopentene compound, preparation method and application
  • Photochromic thiophene-thiazole heterocycle hybrid asymmetric perfluorocyclopentene compound, preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] [Example 1]: [Compound 1a]:

[0025] In the molecular structure formula, when R 1 is methyl, R 2 When it is a hydrogen atom, it constitutes the photochromic compound 1a, and its name is: [1-(2,4-dimethylthiazol-5-yl), 2-[2-methyl-5-phenylthiophene-3 -base)] perfluorocyclopentene (1a), the structural formula is as follows:

[0026]

[0027] The synthetic scheme Scheme 1 of this novel diaryl perfluorocyclopentene photochromic compound is shown in Scheme 1: Scheme 1:

[0028]

[0029] Concrete synthetic steps are as follows:

[0030] 1.3,5-Dibromo-2-methylthiophene (5)

[0031] Under ice-bath conditions, dissolve 2-methylthiophene (4) (25.617g, 261.4mmol) in acetic acid, add dropwise acetic acid containing liquid bromine under stirring, continue the ice-bath reaction for 8h, add water, water Na 2 CO 3 After neutralization, extract with ether, combine the organic phases, and wash with saturated Na 2 CO 3 and aqueous solution successively, anhydrous MgSO 4 Dr...

Embodiment 2

[0048] [Example 2]: [Compound 2a]:

[0049] In the molecular structure formula, when R 1 is methyl, R 2 When it is a para-nitrile group, it constitutes a photochromic compound 2a, and its name is: [1-(2,4-dimethylthiazol-5-yl), 2-[2-methyl-5-(4- Nitrile phenyl) thiophen-3-yl)] perfluorocyclopentene (2a), the structural formula is as follows:

[0050]

[0051] The synthetic scheme Scheme 2 of this novel diaryl perfluorocyclopentene photochromic compound is shown in Scheme 2: Scheme 2:

[0052]

[0053] Concrete synthetic steps are as follows:

[0054] 1.3-Bromo-2-methyl-5-(4-cyanophenyl)thiophene (11)

[0055] Under nitrogen protection, 4-cyanobromobenzene (2.5g, 13.74mmol) and Pd(PPh 3 ) 4 (0.5g) was dissolved in 80mlTHF, after stirring for 20min, 6 (3.10g, 14mmol) was added and the concentration was 2.0mol / L Na 2 CO 3 Solution 50ml, heated to reflux for 16h, stop the reaction, cooled to room temperature. The liquids were separated, the aqueous phase was extract...

Embodiment 3

[0060] [Example 3]: [Compound 3a]:

[0061] In the molecular structure formula, when R 1 is methyl, R 2 When it is para-fluorine, it constitutes photochromic compound 3a, and its name is: [1-(2,4-dimethylthiazol-5-yl), 2-[2-methyl-5-(4-fluoro Phenyl) thiophen-3-yl)] perfluorocyclopentene (3a), the structural formula is as follows:

[0062]

[0063] The synthetic scheme Scheme 3 of this novel diaryl perfluorocyclopentene photochromic compound is shown in Scheme 3: Scheme 3:

[0064]

[0065] Concrete synthetic steps are as follows:

[0066] 1. 3-Bromo-2-methyl-5-(4-methoxyphenyl)thiophene (12)

[0067] Under nitrogen protection, 4-methoxybromobenzene (1.24g, 7.07mmol) and Pd(PPh 3 ) 4 (0.4g) was dissolved in 70mlTHF, after stirring for 20min, 6 (1.59g, 7.20mmol) was added and the concentration was 2.0mol / LNa 2 CO 3Solution 30ml, heated to reflux for 16h, stop the reaction, cooled to room temperature. The liquids were separated, the aqueous phase was extracted wit...

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Abstract

The invention discloses a photochromic thiophene-thiazole heterocycle hybrid asymmetric perfluorocyclopentene compound, a preparation method and application. The photochromic material can keep good photochromic performance in solution or films, has good chemical and thermal stability, remarkable fatigue resistance, high cyclized quantum yield, good sensitivity and the like in an open ring state (a colorless state) and a closed ring state (a color state), and has appointed absorption wavelength; the absorption spectrum in the color state is between 400 and 600 nanometers and is just matched with a laser device with the wavelength of 532 nanometers; the photochromic material can be used for the preparation of an organic photochromic photon recording medium with shorter wavelength, and also can be used for fluorescence detection and a fluorescent light-operated switch; and the photochromic material is primarily used for high-density holographic optical storage, and the storage attribute of the photochromic material is erasable photon type storage.

Description

technical field [0001] The invention belongs to the field of organic photochromic materials, in particular to a photochromic thienthiazole heterocyclic mixed-linked asymmetric perfluorocyclopentene compound, a preparation method and an application thereof. Background technique [0002] The rapid development of information technology has put forward higher and higher requirements for the capacity and data transmission rate of optical storage systems: it must not only meet high storage density, high data transmission rate, high storage life and high erasing times, but also have simple and economical features. Advantages of equipment and low price information bits. As a new generation of storage technology, erasable and rewritable optical discs have been practically achieved through breakthroughs in magneto-optic and phase-change materials based on inorganic media. Due to the advantages of long storage life, non-contact read / write / erase, high carrier-to-noise ratio of informat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D409/08C09K9/02G11B7/244H01L51/50H01L51/54
Inventor 蒲守智刘刚杨天赦刘卫军崔士强
Owner JIANGXI SCI & TECH NORMAL UNIV
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