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Multiple thiophene group-containing photochromic compound

A photochromic and compound technology, applied in the fields of silicon organic compounds, color-changing fluorescent materials, organic chemistry, etc., can solve the problems of difficult optical information storage, difficult preparation of mixed crystal materials, and difficulty in mass production, and achieve good dissolution. high stability, easy bridging and good thermal stability

Active Publication Date: 2011-04-13
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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  • Multiple thiophene group-containing photochromic compound
  • Multiple thiophene group-containing photochromic compound
  • Multiple thiophene group-containing photochromic compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Preparation of 2,3,4,5-tetrakis(2',5'-dimethyl-3'-thiophene) basethiophene (compound I-1)

[0044]

[0045] In the 50ml two-necked bottle, add tetrabromothiophene 1mmol (compound 3), Ni(dppp)Cl successively 2 and THF, evacuated, Ar 2 Gas displacement, then dropwise thereinto 2,5-dimethyl-3-thiophene magnesium bromide (compound 2, it is made of 5mmol 2,5-dimethyl-3-bromothiophene (compound 1) with 6mmol 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%. 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; Fo...

Embodiment 2

[0047] Preparation of 2,3,4,5-tetrakis(2',5'-dimethyl-3'-thiophene) basethiophene (compound I-1)

[0048]

[0049] 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

[0051] Preparation of 3,4-two (5'-methyl-2'-thiophene) base-2,5-bis(2',5'-dimethyl-3'-thiophene) base thiophene (compound I-2)

[0052]

[0053] 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 in 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 wit...

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Abstract

The invention relates to a multiple thiophene group-containing photochromic compound. A five-membered aromatic heterocycle is taken as a bridge, different numbers of substitute thiophene rings are arranged at the periphery of the five-membered aromatic heterocycle, or / and substitute thiophene rings are arranged at different bridging positions of the five-membered aromatic heterocycle, and the multiple thiophene group-containing photochromic compound is obtained. The multiple thiophene group-containing photochromic compound can realize reversible change of a plurality of colors under the radiation of light with different wavelengths.

Description

technical field [0001] 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 [0002] 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 by using light without special processing, which makes it have broad application prospects in various high-tech fields such as photonic switches, especially organic controllable optical information storage mater...

Claims

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Application Information

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IPC IPC(8): C07D333/08C07F7/08C07D333/48C09K9/02
Inventor 罗千福凌祥陈春蕾张国程慧
Owner SHANGHAI GANTIAN OPTICAL MATERIALS
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