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Material with long-service-life room-temperature phosphorescence phenomenon, preparation method and application

A room-temperature phosphorescence and long-life technology, applied in luminescent materials, chemical instruments and methods, organic chemistry, etc., can solve problems such as the difficulty in synthesis of inorganic long-lasting materials and the doping of heavy metal elements, and achieve cheap raw materials, simple preparation, and wide application foreground effect

Active Publication Date: 2019-05-17
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Purpose of the invention: The purpose of the invention is to provide a material with long-life room temperature phosphorescence, which overcomes the disadvantages of difficulty in the synthesis of inorganic long-lasting materials and the need for doping with heavy metal elements

Method used

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  • Material with long-service-life room-temperature phosphorescence phenomenon, preparation method and application
  • Material with long-service-life room-temperature phosphorescence phenomenon, preparation method and application
  • Material with long-service-life room-temperature phosphorescence phenomenon, preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Example 1: Synthesis of compound Ben-H.

[0030] Dissolve 1.17g of indole and 1.06g of benzaldehyde in anaerobic dichloromethane, add 0.1mL trifluoroacetic acid in the dark, react in the dark for 24 hours at room temperature, filter the solid with suction and wash with dichloromethane to obtain Compound Ben-H, the yield is 36.5%. 1 H NMR (400MHz, DMSO-d 6 )δ=10.70(s, 2H), 7.34(d, J=7.5Hz, 4H), 7.29(t, J=7.4Hz, 4H), 7.22(dd, J=14.9, 6.9Hz, 4H), 7.08( d, J=7.9Hz, 2H), 6.95(t, J=7.6Hz, 2H), 6.79(t, J=7.5Hz, 2H), 5.70(s, 2H). The compound is dissolved in dimethyl sulfoxide, and crystals are obtained after standing still for a period of time, and the thermal ellipsoid diagram of the crystal is shown in figure 1 shown. The synthetic route is as follows:

[0031]

Embodiment 2

[0032] Example 2: Synthesis of compound Ben-Ox.

[0033] 410.5 mg of Ben-H and 507.6 mg of iodine were dissolved in 30 mL of acetonitrile solvent and reacted in the dark for 8 hours under heating at 80 degrees Celsius. The solid was obtained by suction filtration and washed with cold acetonitrile to obtain the compound Ben-Ox with a yield of 44.1%. 1 H NMR (400MHz, DMSO-d 6 )δ=10.53(s, 2H), 7.78-7.63(m, 10H), 7.45(d, J=8.0Hz, 2H), 7.29-7.22(m, 2H), 7.06(d, J=8.1Hz, 2H ), 6.87-6.77 (m, 2H). The compound is dissolved in dimethyl sulfoxide, and crystals are obtained after standing still for a period of time, and the thermal ellipsoid diagram of the crystal is shown in figure 2 shown. The synthetic route is as follows:

[0034]

Embodiment 3

[0035] Example 3: Synthesis of Compound Ben-2S.

[0036] Dissolve 410.5mg of Ben-H and 5mg of benzyltriethylammonium chloride in 20mL of dimethyl sulfoxide, add 1mL of potassium hydroxide aqueous solution (50% mass ratio) under nitrogen atmosphere, and then slowly add 377.6mg of (S) -1-bromo-2-methylbutane, reacted at room temperature for 2 hours, added a large amount of water to wash away dimethyl sulfoxide to obtain a solid, separated by column chromatography, and the eluent ratio was dichloromethane / petroleum ether= 1:5, the compound Ben-2S was obtained with a yield of 51%. 1 H NMR (400MHz, CDCl 3 )δ=7.52(t, J=7.1Hz, 2H), 7.34(d, J=7.3Hz, 4H), 7.28-7.22(m, 4H), 7.22-7.13(m, 4H), 7.10(m, 2H ), 6.98(m, 2H), 5.82(q, J=3.5Hz, 2H), 3.87-3.58(m, 4H), 1.96-1.80(m, 2H), 1.43-1.28(m, 2H), 1.26- 1.10 (m, 2H), 0.94-0.84 (m, 9H), 0.74 (d, J=6.6Hz, 3H). The compound is dissolved in dichloromethane, and crystals are obtained after standing still for a period of time, and the thermal ...

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Abstract

The invention discloses a material with a long-service-life room-temperature phosphorescence phenomenon, a preparation method and application. The material is prepared from an organic compound takingindolo-indole or indolocarbazole as a basic unit, wherein the organic compound has a structural general formula of a general formula I shown in the description, wherein Ar is an aromatic group or a derivative group thereof; R is a hydrogen atom or an alkyl chain, an olefin chain and a derivative group which contain 1-18 carbon atoms; and an R' position is a hydrogen atom or does not contain atoms.According to the material, the defects that an inorganic long afterglow material is difficult to synthesize and heavy metal elements need to be doped are overcome, and the material disclosed by the invention has the long-service-life room-temperature phosphorescence phenomenon.

Description

technical field [0001] The invention relates to a preparation method and application of an organic phosphorescence luminescent material, in particular to a material with long-life room temperature phosphorescence, a preparation method and an application. Background technique [0002] Long-life room temperature phosphorescent materials are also called long afterglow materials, which essentially use the photoluminescence phenomenon of materials, which means that materials can continue to emit light after absorbing energy and removing the excitation source. Such materials have broad application prospects in anti-counterfeiting, lighting, display, warning signs, biological imaging and other fields. [0003] Among them, inorganic long-lasting materials have a long history of application, and the synthesis process is relatively mature. Many natural ores contain long-lasting materials. However, the preparation of inorganic materials is difficult and the conditions are harsh, and t...

Claims

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Application Information

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IPC IPC(8): C07D487/04C09K11/06
Inventor 刘淑娟李飞阳赵强郭颂黄维
Owner NANJING UNIV OF POSTS & TELECOMM
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