Acenaphthylene derivative

A technology of derivatives, acenaphthylene, applied in the field of acenaphthylene derivatives, can solve the problems of increasing costs, various parameters, harsh reaction conditions, etc., and achieve the effect of simple synthesis route and mild reaction conditions

Active Publication Date: 2009-12-30
丹玥光学(上海)有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The bigger the molecule, the more combinations of properties, the more harsh the reaction conditions, so it will inevitably lead to an increase in cost, or the average of various parameters, and it is still rare to find an ideal material that can truly achieve marketization.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Preparation of 1,2-bis(3-methyl-2-thienyl)acenaphthylenene.

[0028] 6.2 g of the haloacenaphthylene compound and the catalyst were added to 50 ml of ether, and a reagent made of 2-halo-3-methylthiophene and magnesium powder was added dropwise at room temperature. After the dropwise addition was completed, the reaction was carried out for 12 hours. Dilute hydrochloric acid was poured into the reaction mixture to terminate the reaction. The organic phase was separated and the aqueous phase was extracted with ether (3 x 25ml). 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 through a short silica gel column with petroleum ether as the eluent to obtain 5.1 g of solid with a yield of about 74%.

[0029] H NMR spectrum of the product: 1 H-NMR (500MZ, CDCl 3 , ppm) δ H 7.90 (m, 4H), 7.65 (m, 2H), 7.37 (d, 2H), 6.98 (d, 2H), 1.99 (s, 6H). Ma...

Embodiment 2

[0031] Synthesis of 1,2-bis(3,5-dimethyl-2-thienyl)acenaphthylenene.

[0032] 3,5-Dimethyl-2-thiopheneboronic acid (20mmol) and 1,2-dihaloacenaphthylenene (10mmol) were respectively added into a 100mL one-necked flask. Use tetrahydrofuran as a solvent for the reaction; and add a catalyst. Argon vacuum replaced the system three times, and refluxed overnight in an argon atmosphere in the dark. Pour into water, separate the layers, extract the inorganic phase with ether, combine the organic layers, and concentrate. Using petroleum ether and dichloromethane as the eluent, pass through a silica gel column. An orange-red solid was obtained in 81% yield.

[0033] H NMR spectrum of the product: 1 H-NMR (500MZ, CDCl 3 , ppm) δ H 7.81 (d, 2H), 7.64 (d, 2H), 7.55 (m, 2H), 6.60 (s, 2H), 2.41 (s, 6H), 2.22 (s, 6H). Mass spectrometry: EI-MS, M + / e:372.4

Embodiment 3

[0035] Preparation of 1,2-bis(3,4,5-trimethyl-2-thienyl)acenaphthylenene.

[0036] Add 20 mmol of dihaloacenaphthylene compound and catalyst together into 50 mL of ether, and dropwise add an organic reagent made of 2-halogenated 3,4,5-trimethylthiophene and magnesium powder. 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 through a short silica gel column with petroleum ether as the eluent to obtain a pure product with a yield of about 69%.

[0037] Proton NMR spectrum: 1 H-NMR (500MZ, CDCl 3 , ppm) δ H 7.91 (d, 2H), 7.74 (d, 2H), 7.59 (m, 2H), 2.25 (s, 6H), 2.41 (s, 6H), 2.12 (s, 6...

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Abstract

The invention relates to an acenaphthylene derivative of which structure is shown in formula I. The acenaphthylene derivative designed in the invention has the unique structure that the color of the derivative can be red, yellow or blue by regulating the bridging position of the thiophene of the acenaphthylene derivative under the irradiation of lights of different wavelengths. The acenaphthylene derivative of the invention can applied in the fields of building decoration, special protection, full color display, multi-dimensional information storage and readout and the like. In the formula I, R1, R2 and R3 are respectively one of hydrogen, alkyl group, aryl group, halogen, hydroxyl group, aldehyde group, carboxyl group, sulfonic group, -COOMe and -SO3Me(Me is metal); n is an integer between one to three and m is an integer between one to three.

Description

technical field [0001] The present invention relates to an acenaphthylene derivative. Background technique [0002] Among many organic photochromic materials, due to the good thermal stability of diarylethene (-20-80 ℃ no configuration transformation for a long time); ); high closed-loop quantum efficiency (mostly can reach more than 30%); fast response time (switching ring is between several picoseconds), and it is considered to be possible to meet the high potential of high speed and large capacity One of the storage materials. Due to the series of useful properties of dithienylethylene, scientists have devoted a lot of enthusiasm and energy in designing and synthesizing these compounds in recent years. The purpose of these research and development, on the one hand, is to expect to construct new molecular materials that may have advanced or new properties; match the condition. [0003] Although many molecular materials in this area have been researched and developed, e...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/08C09K9/02
Inventor 罗千福刘熠陈春蕾凌祥
Owner 丹玥光学(上海)有限公司
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