Dithiophene ethene functional material, and its preparing method and use

Abstract

The invention belongs to the technical field of diarylethylene photic color-changing material, relating to a diarylethylene photic color-changing monomer or polymer whose main chain contains a single or plural alkyl fluorenes, which remarkably raise closed loop quantum efficiency of the material; and the long chain alkyl makes the polymer possess very good solubility, beneficial to polymer rotary coating to form film. The fluorescence of the polymer changes obviously before and after photic changing color, and thus the polymer has very good fluorescent ON and OFF performances. The synthesizing route is convenient and compact, and the polymerization degree is high. The material can be applied to the fields of high density information storage, molecular switches, molecular lead wires, etc.

Description

technical field

[0001] The invention belongs to the technical field of diarylethene photochromic materials, and in particular relates to the structural design, preparation method and application performance development of a diarylethene photochromic compound. Specifically, it relates to a preparation method of a diarylethene photochromic monomer or polymer containing single or multiple alkyl fluorenes in the main chain, a color changing method and application conditions of a fluorescent switch. Background technique

[0002] The 21st century is the information century. Massive information storage and high-speed transmission have become the requirements for the further development of high-tech information industries. Optical information storage has become one of the frontier topics in the field of major science and technology recognized today. Moreover, with the rapid development of modern science and technology, faster and larger-capacity information storage materials are req...

Examples

Embodiment 1

[0033] The preparation method of embodiment 1 target polymer A:

[0034] Mix and dissolve halogenated dithiophene-substituted maleic dinitrile and 2,7-diboronic acid ethyl ester-9,9'-dioctylfluorene in a mass ratio of 1:2 in dry solvent tetrahydrofuran or toluene, add 2.5M Concentration of Na 2 CO 3 130 ml of aqueous solution and catalyst triphenylphosphopalladium (2‰ of the mass of halodithiophene substituted malonitrile). The whole reaction system is placed under the protection of inert gas. At 80°C, the reaction was stirred for 8 hours. After the reaction was completed, the mother liquor was cooled to room temperature, poured into a stirred mixed solvent of organic solvent methanol and deionized water (the weight ratio of the two was 8:1), and filtered to obtain a solid product. After washing the product repeatedly with water or methanol, Soxhlet extraction for one day, and vacuum drying to obtain the final product. The yield is about 68%.

Embodiment 2

[0035] The synthesis of embodiment 2 target object B:

[0036] In a 100mL one-necked flask, add ethyl bisborate substituted-dioctylbisdifluorene, 1,2-methyl-1,2-bis(2-methyl-5-halo-3-thiophene)-ethylene 10 mmol, THF was used as the solvent for the reaction (150 ml), and 0.03 mmol of catalyst was added and 50 ml of 2M NaOH aqueous solution was added. Argon vacuum replaced the system three times, and refluxed overnight in an argon atmosphere in the dark. After the reaction is completed, the mother liquor is poured into a mixed solvent of methanol and deionized water, filtered, washed with water and methanol respectively, subjected to Soxhlet extraction for 24 hours, and vacuum-dried to obtain the desired product.

Embodiment 3

[0037] The preparation of embodiment 3 target polymer C:

[0038] Mix and dissolve 5 mmol of brominated diarylmaleic dinitrile and ethyl bisborate substituted-dioctyl tertiary fluorene in a ratio of 1:1 in 120 ml of tetrahydrofuran solvent, add 30 ml of 2M NaOH aqueous solution and 2.5‰ (0.1 mmol) catalyst triphenylphosphopalladium. The reaction system was placed under protection from light and inert gas. The reaction was stirred at 60°C for 72 hours. After the reaction was completed, the mother liquor was cooled to room temperature, poured into a stirred mixed solvent of organic solvent methanol and deionized water (ratio: 10:1), and filtered to obtain a solid product. After washing the product with water or methanol, Soxhlet extraction for 36 hours, and vacuum drying to obtain the final product.

technical field

[0001] The invention belongs to the technical field of diarylethene photochromic materials, and in particular relates to the structural design, preparation method and application performance development of a diarylethene photochromic compound. Specifically, it relates to a preparation method of a diarylethene photochromic monomer or polymer containing single or multiple alkyl fluorenes in the main chain, a color changing method and application conditions of a fluorescent switch. Background technique

[0002] The 21st century is the information century. Massive information storage and high-speed transmission have become the requirements for the further development of high-tech information industries. Optical information storage has become one of the frontier topics in the field of major science and technology recognized today. Moreover, with the rapid development of modern science and technology, faster and larger-capacity information storage materials are req...

Examples

Embodiment 1

[0033] The preparation method of embodiment 1 target polymer A:

[0034] Mix and dissolve halogenated dithiophene-substituted maleic dinitrile and 2,7-diboronic acid ethyl ester-9,9'-dioctylfluorene in a mass ratio of 1:2 in dry solvent tetrahydrofuran or toluene, add 2.5M Concentration of Na 2 CO 3 130 ml of aqueous solution and catalyst triphenylphosphopalladium (2‰ of the mass of halodithiophene substituted malonitrile). The whole reaction system is placed under the protection of inert gas. At 80°C, the reaction was stirred for 8 hours. After the reaction was completed, the mother liquor was cooled to room temperature, poured into a stirred mixed solvent of organic solvent methanol and deionized water (the weight ratio of the two was 8:1), and filtered to obtain a solid product. After washing the product repeatedly with water or methanol, Soxhlet extraction for one day, and vacuum drying to obtain the final product. The yield is about 68%.

Embodiment 2

[0035] The synthesis of embodiment 2 target object B:

[0036] In a 100mL one-necked flask, add ethyl bisborate substituted-dioctylbisdifluorene, 1,2-methyl-1,2-bis(2-methyl-5-halo-3-thiophene)-ethylene 10 mmol, THF was used as the solvent for the reaction (150 ml), and 0.03 mmol of catalyst was added and 50 ml of 2M NaOH aqueous solution was added. Argon vacuum replaced the system three times, and refluxed overnight in an argon atmosphere in the dark. After the reaction is completed, the mother liquor is poured into a mixed solvent of methanol and deionized water, filtered, washed with water and methanol respectively, subjected to Soxhlet extraction for 24 hours, and vacuum-dried to obtain the desired product.

Embodiment 3

[0037] The preparation of embodiment 3 target polymer C:

[0038] Mix and dissolve 5 mmol of brominated diarylmaleic dinitrile and ethyl bisborate substituted-dioctyl tertiary fluorene in a ratio of 1:1 in 120 ml of tetrahydrofuran solvent, add 30 ml of 2M NaOH aqueous solution and 2.5‰ (0.1 mmol) catalyst triphenylphosphopalladium. The reaction system was placed under protection from light and inert gas. The reaction was stirred at 60°C for 72 hours. After the reaction was completed, the mother liquor was cooled to room temperature, poured into a stirred mixed solvent of organic solvent methanol and deionized water (ratio: 10:1), and filtered to obtain a solid product. After washing the product with water or methanol, Soxhlet extraction for 36 hours, and vacuum drying to obtain the final product.

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