Metal aza porphyrin compound containing fluorene diaryl ethylene and its preparation method and application

A diarylethene compound technology, which is applied in the field of diarylethene metal azaporphyrin compounds and its preparation, can solve the problems of destroying information, authenticity and integrity of ring-destroying information records, etc.

Inactive Publication Date: 2006-01-25
方圆环球光电技术盐城有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Obviously, in these two methods of using the difference in the UV-Vis absorption spectrum as a readout method, the light used for readout can also write or erase information, which may cau

Method used

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  • Metal aza porphyrin compound containing fluorene diaryl ethylene and its preparation method and application
  • Metal aza porphyrin compound containing fluorene diaryl ethylene and its preparation method and application
  • Metal aza porphyrin compound containing fluorene diaryl ethylene and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Example 1 Using Method 1 to synthesize target compound M 1

[0051] The synthesis of intermediate: In a 100mL single-necked flask, 3mmol of 2-halo-9,9'-dioctylfluorene, 1,2-dianitrile-1,2-bis(2-methyl-5-halo -3-thiophene)-ethylene 1.3mmol, metal magnesium or sodium; use tetrahydrofuran or ether as solvent, and add a certain catalyst. The system was replaced with argon in vacuum three times, and refluxed overnight in an argon atmosphere, protected from light. Pour into water, separate the layers, extract the inorganic phase with ether, combine the organic layers, and concentrate. Use petroleum ether and dichloromethane as eluents to pass through a silica gel column. The obtained light yellow solid is the intermediate with a yield of 64%. MS(m / e): 1047.8. 1 H-NMR (400MHz, CDCl 3 , Ppm): 0.86 (t, 12H, -CH 3 ), 2.23(s, 6H, -CH 3 ), 6.62(s, 2H, -CH-), 1.02-1.23(m, 48H, -CH 2 -), 1.95(m, 8H, -CH 2 -), 7.25-7.36 (m, 4H, Ar) 7.43-7.48 (m, 6H, Ar) 7.79-7.84 (m, 4H, Ar).

[0052] ...

Embodiment 2

[0055] Example 2 Using method 2 to synthesize target compound M 1

[0056] Under the protection of argon, add 20mmol of metallic magnesium to 100mL of dry isopropanol and reflux for 24 hours; cool to room temperature, and then add 2mmol of 1,2-diconitrile-1,2-bis(2-methyl- The 5-halo-3-thiophene)-ethylene compound was refluxed for 36 hours. The reaction was carried out under protection from light and argon. After the reaction was completed, it was cooled, the solvent was removed under reduced pressure, washed, dried, filtered, concentrated, Silica gel column to obtain pure octahalodithiophene vinyl metal azaporphyrin compound. The yield is about 55%.

[0057]

[0058] Then, the azaporphyrin is reacted with 2-halo-9,9'-dioctylfluorene in a polar solvent under the action of a catalyst, and refluxed overnight in an argon atmosphere, protected from light. Cool to room temperature, filter, concentrate, use chloroform or dichloromethane and petroleum ether as the eluent, and pass thr...

Embodiment 3

[0059] Example 3 Photochromic color development method

[0060] Before being irradiated with ultraviolet light, the target compound in Example 1 or 2-the azaporphyrin compound has three strong absorption peaks, located at 653nm, 340nm and 315nm, and a weak broad absorption band, located between 400-450nm between. When its methylene chloride solution or chloroform is irradiated with ultraviolet light with a wavelength of 300-365nm, its absorption spectrum changes significantly. The figure below shows the dynamic change spectrum obtained at different intervals. We can clearly see that the strong absorption peak at 653nm gradually weakened, while a new absorption peak appeared at about 720nm and gradually increased. After about 30 minutes of irradiation, the system reached a light-stable state, and a set of isoabsorption points appeared at 320, 396, 471, 570, and 683 nm. The color of the solution also changed from blue-green to dark green. The new absorption peak at 720nm is due to t...

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PUM

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Abstract

The invention discloses a fluorine-containing diarylethylene metal aza porphyrin compound, its synthesizing method and application, wherein the compound has a rather large molar absorption coefficient and strong near-infrared fluorescence-emission, the charge of alkyl fluorine can increase the solubility of the material in organic solvent and its light-emitting performance. By employing the opening/closing ring reaction of the dithiofuran ethylene, the fluorescent change of the compound can be adjusted, and the non-destructive reading out can be achieved.

Description

Technical field [0001] The invention belongs to the technical field of photochromic materials, and in particular relates to a diarylvinyl metal azaporphyrin compound and a preparation method and application thereof. Specifically, it relates to a dithiopheneethylene substituted metal azaporphyrin compound containing polyalkyl fluorene, a preparation method thereof, and applications in the fields of luminescence and color change. Background technique [0002] Photochromic compounds have attracted more and more attention due to their potential application value in light energy memory, information storage, coatings, pigments and related industries. With the rapid development of cutting-edge technologies such as modern biology and aerospace, more rapid and super-capacity information storage materials are required. The response time even hopes to reach the nanosecond and picosecond level. The ultimate goal is to store information at the molecular or even atomic level. High-performance ...

Claims

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Application Information

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IPC IPC(8): C07D487/22C07F3/00C07F1/08C07F7/22C07F7/30C07F15/00C07D209/00C07D257/00
Inventor 黄维罗千福
Owner 方圆环球光电技术盐城有限公司
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