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Bi(diaryl methylene)-dihydro acene compound aggregation-induced emission and aggregation-promoting photochromism

A compound, dialkylamino technology, applied in luminescent materials, chemical instruments and methods, organic chemistry, etc., can solve problems such as unclear mechanism of RIR

Active Publication Date: 2017-08-01
唐本忠
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, some emerging AIE systems do not have multiple rotors, making the RIR mechanism unclear

Method used

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  • Bi(diaryl methylene)-dihydro acene compound aggregation-induced emission and aggregation-promoting photochromism
  • Bi(diaryl methylene)-dihydro acene compound aggregation-induced emission and aggregation-promoting photochromism
  • Bi(diaryl methylene)-dihydro acene compound aggregation-induced emission and aggregation-promoting photochromism

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0101] Step (1): Preparation of 5,12-bis(dibromomethylene)-5,12-dihydrotetracene

[0102] CBr 4 (8.6g, 25.9mmol) with PPh 3 (13.6g, 51.8mmol) in 100mL of dry toluene, stirred at room temperature for 30 minutes, then added 5,12-tetrabenzoquinone (2.06g, 8.0mmol) in one portion, and the solution was heated to reflux for 24 hours. The reaction mixture was cooled to room temperature, and the solid was removed by filtration and washed with toluene. The filtrate was concentrated under reduced pressure to obtain a crude product. The crude product was ground by adding ethanol, and the pure product (4.3 g) was obtained after filtration with a yield of 95%.

[0103] 1H-NMR (CDCl 3 )δ (ppm): 8.26 (s, 2H), 7.86 (m, 4H), 7.3 (dd, J 1 =6.4Hz,J 2 =3.2Hz,2H),7.31(dd,J 1 =5.6Hz,J 2 =3.2Hz,2H). 13 C-NMR (CDCl 3 )δ (ppm): 90.59, 127.25, 127.33, 127.44, 127.93, 128.29, 131.79, 133.36, 136.17, 139.73. MALDI-TOF mass: m / z=569.7479 (cacld.569.7475).

[0104] Step (2): Preparation of 5,12-...

Embodiment 2

[0109] To a solution of 5,12-bis(dibromomethylene)-5,12-dihydronaphthacene (2.26 g, 4.0 mmol) and 2-thionylboronic acid (4.10 g, 32 mmol) in 100 mL of toluene, Add 5 mL of ethanol and 5 mL of water. The mixture was stirred at room temperature with nitrogen bubbled through for 30 minutes. Then add K all at once 2 CO 3 (5.52g, 40mmol) and Pd(PPh 3 ) 4 (0.23g, 0.20mmol), and the mixture was heated to reflux for 24 hours. The reaction mixture was cooled to room temperature, filtered through a filter plate (silica gel thickness: 5 cm), washed with dichloromethane until the filtrate was clear. The filtrate was concentrated under reduced pressure to obtain a crude product. The crude product was ground by adding ethanol, and the product (1.86 g) was obtained after filtration with a yield of 80%.

[0110] After the product was dissolved in chloroform, it was placed in a hexane environment, and high-purity colorless crystals were obtained after 2 days.

Embodiment 3

[0112]

[0113] Method S1 Synthesis of 9,10-bis(diarylmethylene)-9,10-dihydroanthracene (R-DHA)

[0114] Reagents and conditions: (i) CBr 4 ,PPh 3 , toluene, 80°C; (ii) arylboronic acid, [PPh 3 ] 4 Pd, K 2 CO 3 , toluene, 110°C.

[0115] Step (1): Synthesis of 9,10-bis(dibromomethylene)-9,10-dihydroanthracene:

[0116] CBr 4 (14.940g, 45.00mmol) and PPh 3 (20.960g, 80mmol) in 100mL of dry toluene was stirred at room temperature for 20 minutes, then anthracene-9,10-dione (2.080g, 10mmol) was added in one portion, and the solution was heated to 80°C for 24 hours. The reaction mixture was cooled to room temperature, and the solid was removed by filtration, washed with toluene, and the filtrate was rotovapped to obtain a crude product. The crude product was ground by adding ethanol, and the pure product (4.120 g) was obtained after filtration with a yield of 78%. 1 H-NMR (CDCl 3 ), δ(ppm): 7.83(m, J=3.2Hz, 4H), 7.28(m, J=3.2Hz, 4H); 13 C-NMR (CDCl 3 )δ (ppm): 139.5...

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Abstract

The invention provides a series of novel bi(diaryl methylene)-dihydro acene compounds having aggregation-induced emission characteristics and application of the same in organic photochromic materials.

Description

[0001] This application claims priority to US Provisional Application No. 62 / 071,688, filed September 30, 2014. The entirety of the aforementioned application is incorporated by reference into the present application. technical field [0002] The invention relates to a series of novel polycyclic molecular bis(diarylmethylene)-dihydroacene compounds with aggregation-induced luminescent properties and their application as organic photochromic materials. Background technique [0003] Aggregation-induced emission (AIE) refers to the following phenomenon: a type of luminophore does not emit light in the molecular state, but will transform into strong emission when aggregated into aggregates. Luminescent materials with AIE properties have attracted widespread interest and found a variety of applications. Through the mechanistic interpretation of photophysical processes, structure-property relationships have been obtained, and structural design strategies for generating new AIE lu...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07C15/28C07C15/60H01L51/54
Inventor 唐本忠何自开林荣业
Owner 唐本忠
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