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Preparation method of 9, 10-bis (di(pyridine-4-yl) methylene)-9, 10-dihydroanthracene

A technology of dibromomethylene and 10-, which is applied in the field of preparation of organic compounds, achieves the effect of wide application value and simple preparation method

Pending Publication Date: 2021-10-08
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, according to the current research, the various properties of photochromic compounds cannot fully meet the needs of people's daily life applications.

Method used

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  • Preparation method of 9, 10-bis (di(pyridine-4-yl) methylene)-9, 10-dihydroanthracene
  • Preparation method of 9, 10-bis (di(pyridine-4-yl) methylene)-9, 10-dihydroanthracene
  • Preparation method of 9, 10-bis (di(pyridine-4-yl) methylene)-9, 10-dihydroanthracene

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Add 9,10-bis(dibromomethylene)-9,10-dihydroanthracene, 4-pyridineboronic acid, anhydrous sodium carbonate, triphenylphosphine into 500ml 1,4-dioxane / H 2 O (V:V=4 / 1) mixed solvent, after heating to 120° C. under nitrogen atmosphere, palladium acetate was added to react for 24 hours.

[0034] After the reaction solution was cooled to room temperature, it was transferred to a separatory funnel and added with 300ml of water to shake well, then 200ml of ethyl acetate was added to extract three times, the organic phases were combined and dried with anhydrous sodium sulfate, filtered and rotary evaporated under reduced pressure.

[0035] The crude product was obtained by flash column chromatography using methanol / dichloromethane (V / V=1:10) as the eluent, and 3 g of the crude product was added to 150 ml of acetonitrile, heated and stirred until boiling and then filtered while hot, and this operation was repeated for 3 Once, the product white solid powder 9,10-bis(bis(pyridin-4-...

Embodiment 2

[0041] 9,10-bis(dibromomethylene)-9,10-dihydroanthracene (5.2g, 10mmol), 4-pyridineboronic acid (9.8g, 80mmol), anhydrous sodium carbonate (10.6g, 100mmol), Triphenylphosphine (1.3g, 5mmol) was added to 500ml 1,4-dioxane / H 2 O (V:V=4 / 1) mixed solvent, after heating under nitrogen atmosphere, add palladium acetate to react, the reaction temperature and reaction time are shown in Table 2.

[0042] After the reaction solution was cooled to room temperature, it was transferred to a separatory funnel and added with 300ml of water to shake well, then 200ml of ethyl acetate was added to extract three times, the organic phases were combined and dried with anhydrous sodium sulfate, filtered and rotary evaporated under reduced pressure.

[0043] The crude product was obtained by flash column chromatography using methanol / dichloromethane (V / V=1:10) as the eluent, and 3 g of the crude product was added to 150 ml of acetonitrile, heated and stirred until boiling and then filtered while hot...

Embodiment 3

[0048] 9,10-bis(dibromomethylene)-9,10-dihydroanthracene (5.2g, 10mmol), 4-pyridineboronic acid (9.8g, 80mmol), anhydrous sodium carbonate (10.6g, 100mmol), Triphenylphosphine (1.3g, 5mmol) was added to 1,4-dioxane / H 2 In a mixed solvent of O, after heating to 120°C under a nitrogen atmosphere, add palladium acetate to react for 24 hours; where 1,4-dioxane / H 2 The volume and volume ratio of O mixed solvent are shown in Table 3.

[0049] After the reaction solution was cooled to room temperature, it was transferred to a separatory funnel and added with 300ml of water to shake well, then 200ml of ethyl acetate was added to extract three times, the organic phases were combined and dried with anhydrous sodium sulfate, filtered and rotary evaporated under reduced pressure. The crude product was obtained by flash column chromatography using methanol / dichloromethane (V / V=1:10) as the eluent, and 3 g of the crude product was added to 150 ml of acetonitrile, heated and stirred until b...

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Abstract

The invention discloses a preparation method of 9, 10-bis (di(pyridine-4-yl) methylene)-9, 10-dihydroanthracene with a photochromic effect. The 9, 10-bis (di(pyridine-4-yl) methylene)-9, 10-dihydroanthracene is synthesized by mainly using 9, 10-bis (dibromomethylene)-9, 10-dihydroanthracene and 4-pyridylboronic acid as raw materials, water and 1, 4-dioxane as solvents, and triphenylphosphine palladium generated by reaction of triphenylphosphine and palladium acetate as a catalyst under the alkaline condition of sodium carbonate. The preparation method is simple and convenient in synthesis, mild in condition, easy to control and relatively high in yield, and the prepared organic matter has an obvious photochromic effect.

Description

technical field [0001] The invention relates to a preparation method of an organic compound with photochromic effect, in particular to a preparation method of 9,10-bis(bis(pyridin-4-yl)methylene)-9,10-dihydroanthracene. Background technique [0002] Photochromism refers to the reversible transformation of a chemical substance between two isomers with different absorption spectra under light irradiation conditions. There are many kinds of organic photochromic materials, and the reaction mechanisms are also different, mainly including: Heterolysis of bonds, homolysis of bonds, electron transfer tautomerization, cis-trans isomerization, redox reactions, pericyclization reactions, etc. [0003] Photochromic molecules have important applications in the fields of optical memory, switches and actuators (or molecular machines), bioimaging, anti-counterfeiting, and fluorescent sensing (Chem. Rev. 2014, 114, 12174-12277.). After continuous exploration and research, photochromic molec...

Claims

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Application Information

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IPC IPC(8): C07D213/127C09K9/02
CPCC07D213/127C09K9/02C09K2211/1029C09K2211/1011
Inventor 张金方林卓李文静
Owner JIANGNAN UNIV
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