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Photochromic compound containing polythiophene radicals

A photochromic and compound technology, applied in the direction of color-changing fluorescent materials, organic chemistry, chemical instruments and methods, etc., can solve the problems of difficult preparation of mixed crystal materials, difficult large-scale production, difficult optical information storage, etc., to achieve good Solubility, convenient bridging, good thermal stability

Active Publication Date: 2014-08-20
SHANGHAI GANTIAN OPTICAL MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the difficulty in the preparation of mixed crystal materials, and not all organic photochromic compounds can maintain good photochromic properties in the crystal state, and more importantly, it is difficult to produce on a large scale, so it is difficult to be practically applied in optical information on storage

Method used

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  • Photochromic compound containing polythiophene radicals
  • Photochromic compound containing polythiophene radicals
  • Photochromic compound containing polythiophene radicals

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Preparation of 2,3,4,5-tetrakis(2,,5,-dimethyl-3,-thiophene) thiophene (compound Ⅰ-1)

[0045]

[0046] In a 50ml two-necked bottle, add 1mmol of tetrabromothiophene (compound 3), Ni(dppp)Cl 2 and THF, evacuated, Ar 2 gas replacement, and then dropwise added 2,5-dimethyl-3-thiophene magnesium bromide (compound 2, which was prepared from 5 mmol 2,5-dimethyl-3-bromothiophene (compound 1) and 6 mmol magnesium chips ), and heated to 80°C for 12 hours under dark conditions. Cool to room temperature, spin off the solvent, and separate by silica gel column chromatography (petroleum ether) to obtain a light yellow solid product. Yield 33%.

[0047] 1 H NMR (400MHz, CDCl 3 ):δ2.04(s,3H,CH 3 ),2.06(s,3H,CH 3 ),2.10(s,3H,CH 3 ),2.34(s,3H,CH 3 ),2.37(s,6H,CH 3 ),2.41(s,3H,CH 3 ),2.54(s,3H,CH 3 ),6.45(s,1H,thiophene-H),6.50(s,1H,thiophene-H),6.81(s,1H,thiophene-H),6.99(s,1H,thiophene-H).MS(ESI) calcd for C 28 h 28 S 5 :524.08;Found:563.0[M+K] + .

Embodiment 2

[0049] Preparation of 2,3,4,5-tetrakis(2’,5’-dimethyl-3’-thiophene) thiophene (compound Ⅰ-1)

[0050]

[0051] In a 50ml two-necked flask, add 2.5mmol 2,5-dimethyl-3-thiophene boronic acid (compound 4), tetrabromothiophene (0.2g, 0.5mmol), tetrakis(triphenylphosphine) palladium (0.173g, 0.15mmol) , 1ml water, potassium carbonate (0.276g), 30ml toluene and 3ml ethanol, vacuum, Ar 2 Gas replacement, protected from light, heated to 80 ° C for 48 hours. Cool to room temperature, separate the layers, extract the aqueous phase with dichloromethane, combine the organic phases, spin off the solvent, and separate by silica gel column chromatography (petroleum ether) to obtain a yellow solid. Yield 40%. The structural characterization data are the same as in Example 1.

Embodiment 3

[0053] Preparation of 3,4-bis(5'-methyl-2'-thiophene)yl-2,5-bis(2',5'-dimethyl-3'-thiophene)ylthiophene (compound Ⅰ-2)

[0054]

[0055] 0.5 mmol of 3,4-bis(5'-methyl-2'-thiophene)-2,5-dibromothiophene (compound 5) and catalyst (Ni(dppp)Cl 2 ) were added together to 30 mL of diethyl ether, and a diethyl ether solution of a metal organic reagent (compound 2) prepared from 1.5 mmol of 2,5-dimethyl-3-bromothiophene and metal powder was added dropwise. After the dropwise addition was completed, the reaction was carried out overnight. Dilute hydrochloric acid was poured into the reaction mixture to terminate the reaction. The organic phase was separated and the aqueous phase was extracted three times with ether. The organic phases were combined and washed with water. After drying over anhydrous magnesium sulfate, diethyl ether was removed by rotary evaporation. The residue was separated by silica gel column (using petroleum ether as eluent) to obtain compound Ⅰ-2 with a yiel...

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Abstract

The invention relates to a photochromic compound containing polythiophene radicals. The photochromic compound containing polythiophene radicals is obtained by arranging substituted thiophene rings in different numbers in the periphery of a five-membered heteroaromatic ring or / and arranging substituted thiophene rings in different bridging positions of the five-membered heteroaromatic ring based on the five-membered heteroaromatic ring as a bridge. According to the photochromic compound containing polythiophene radicals provided by the invention under irradiating lights of different wavelengths, reversible change of various colors can be realized.

Description

[0001] This application is a divisional application with application number: 201010539206.3, application date: November 11, 2010, and title of invention: photochromic compound containing polythiophene groups. technical field [0002] The invention relates to a photochromic compound containing polythiophene groups, which can be used in the fields of building materials, special protection, multi-color display, full-color printing, multi-dimensional molecular switch characteristics, multi-dimensional information storage and readout, and the like. Background technique [0003] Photochromism refers to a reversible conversion of two isomers with different absorption wavelengths under the action of light of specific wavelength and intensity. Its most intuitive performance is the mutual change of colors. This color change can be widely used in fabric color change, lens dimming, decorative anti-counterfeiting, cosmetics, toys and the like. These changes can be realized quickly only ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D333/48C09K9/02
Inventor 罗千福凌祥陈春蕾张国程慧
Owner SHANGHAI GANTIAN OPTICAL MATERIALS