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A triplet acceptor material with upconversion circularly polarized luminescence and its preparation method and application

A technology of acceptor material and triplet state, which is applied in the direction of luminescent materials, preparation of organic compounds, preparation of amino compounds, etc. It can solve the problems of failing to achieve circularly polarized light emission and circularly polarized light emission.

Active Publication Date: 2018-11-20
THE NAT CENT FOR NANOSCI & TECH NCNST OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, it also failed to achieve circularly polarized light emission
[0006] So far, no circularly polarized light emission has been reported in the field of photon upconversion

Method used

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  • A triplet acceptor material with upconversion circularly polarized luminescence and its preparation method and application
  • A triplet acceptor material with upconversion circularly polarized luminescence and its preparation method and application
  • A triplet acceptor material with upconversion circularly polarized luminescence and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0070] In this embodiment, compound R-1 is synthesized by the following method, and the synthesis process is as follows:

[0071]

[0072] The synthesis method is:

[0073] Weigh 0.28g (R)-1,1'-bi-2-naphthylamine, add it into a reaction tube containing 15mL toluene, add 30mg palladium acetate, 50mg triphenylphosphine, 200mg cesium carbonate and 0.9g 9-( 4-Bromophenyl)-10-phenylanthracene was heated to reflux under the protection of argon, and after 30 hours of reaction, the raw materials were detected by TLC to disappear, that is, the reaction was completed. After cooling down to room temperature, the reaction solution was poured into 100 mL of ethyl acetate for extraction, and the organic phase was dried with anhydrous magnesium sulfate. The solvent was spin-dried and separated by column chromatography to obtain compound R-1 with a yield of 93%.

[0074] NMR 1 H NMR (400MHz, toluene-d8) δ7.99-7.88(m, 6H), 7.85-7.64(m, 8H), 7.44(d, J=8.4Hz, 2H), 7.34-7.23(m, 8H), 7.22-7...

Embodiment 2

[0078] In this example, compound R-1 is synthesized by the following method, the synthetic process is the same as the synthetic process in Example 1, and the synthetic method is:

[0079] Weigh 0.28g of (R)-1,1'-bi-2-naphthylamine, add it into a reaction tube containing 15mL of toluene, add 45.9mg of palladium chloride, 50mg of triphenylphosphine, 318mg of cesium carbonate and 0.4g of 9 -(4-Bromophenyl)-10-phenylanthracene was heated to reflux under the protection of argon, and after 30 hours of reaction, the disappearance of the raw material was detected by TLC, that is, the reaction was completed. After cooling down to room temperature, the reaction solution was poured into 100 mL of ethyl acetate for extraction, and the organic phase was dried with anhydrous magnesium sulfate. The solvent was spin-dried and separated by column chromatography to obtain compound R-1 with a yield of 90%.

[0080] NMR 1 H NMR (400MHz, toluene-d8) δ7.99-7.88(m, 6H), 7.85-7.64(m, 8H), 7.44(d, J...

Embodiment 3

[0083]In this embodiment, compound S-1 is synthesized by the following method, and the synthesis process is as follows:

[0084]

[0085] Weigh 0.28g of (S)-1,1'-bi-2-naphthylamine, add it into a reaction tube containing 15mL of xylene, add 45mg of tetrakis(triphenyl)phosphopalladium, 180mg of sodium bicarbonate and 0.9g of 9 -(4-Bromophenyl)-10-phenylanthracene was heated to reflux under the protection of argon. After 24 hours of reaction, the disappearance of raw materials was detected by TLC, that is, the reaction was completed. After cooling down to room temperature, the reaction solution was poured into 100 mL of ethyl acetate for extraction, and the organic phase was dried with anhydrous magnesium sulfate. Spin dry solvent. Compound S-1 was separated by column chromatography with a yield of 75%.

[0086] NMR 1 H NMR (400MHz, toluene-d8) δ7.99-7.88(m, 6H), 7.85-7.64(m, 8H), 7.44(d, J=8.4Hz, 2H), 7.34-7.23(m, 8H), 7.22-7.15 (m, 6H), 7.14-6.96 (m, 12H), 6.92 (d, J=8....

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Abstract

The invention provides a triplet acceptor material with up-conversion circularly polarized luminescence and a preparation method and application thereof. The triplet acceptor material comprises a chiral structure compound as shown in a formula I or a formula II in the specification. The material has a chiral structure and contains an acene structure in the structure, so that the material can be used as an energy acceptor of a triplet annihilation up-conversion system, and can be matched with an energy donor to achieve the targets of photon up-conversion and emission of circularly polarized light. The triplet acceptor material has great application value in the aspects of chiral photocatalysis, biological imaging, and processing, displaying and storage of optical information.

Description

technical field [0001] The invention belongs to the field of up-conversion materials, and relates to a triplet acceptor material and its preparation method and application, in particular to a triplet acceptor material with up-conversion circularly polarized light emission and its preparation method and application. Background technique [0002] Natural light is composed of rays perpendicular to its propagation direction and vibrating in all directions. If a plane polarizer is placed in the direction of light propagation, only those rays whose vibration direction is parallel to the axis of the polarizer can pass through. This passing light is called plane polarized light. Plane polarized light is superimposed by two circularly polarized lights with the same amplitude and speed but opposite spiral forward directions. When light passes through a medium, if the medium can make the amplitude and speed of left and right circularly polarized light different, elliptically polarized...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C211/58C07C211/61C07C209/10C07D519/00C09K11/06B01J31/02
CPCB01J31/0237B01J31/0244B01J35/004C07C209/10C07C211/58C07C211/61C07D519/00C09K11/06C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1022C09K2211/1029C09K2211/185
Inventor 段鹏飞韩建雷刘鸣华
Owner THE NAT CENT FOR NANOSCI & TECH NCNST OF CHINA
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