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Triplet annihilation agent and preparation method and application thereof

A triplet annihilation and triplet technology, applied in chemical instruments and methods, catalysts, carbon compound catalysts, etc., to achieve the effect of great application value and high luminous quantum efficiency

Active Publication Date: 2021-07-23
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

[0004] So far, the highest quantum efficiency reported in the field of triplet-triplet annihilation photon upconversion is 38%, which is much lower than 50%

Method used

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  • Triplet annihilation agent and preparation method and application thereof
  • Triplet annihilation agent and preparation method and application thereof
  • Triplet annihilation agent and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0068] This embodiment provides a triplet annihilation agent (compound 1), and its structure and preparation flow diagram are as follows:

[0069]

[0070] The synthesis method is:

[0071] Weigh 300mg of 4,12-dibromo[2.2]paracyclic aromatic hydrocarbon, 47mg of tetrakis(triphenylphosphine)palladium, and 783mg of 4,4,5,5-tetramethyl-2-(10-tert-butylperylene-3 -base)-1,3,2-dioxaborolane was added to a 50mL reaction tube, 12mL of toluene was added, 3mL of ultrapure water dissolved with 87mg of sodium carbonate was added, and heated to reflux under nitrogen protection to react 24 After 1 hour, the raw material of 4,12-dibromo[2.2]paracyclic aromatic hydrocarbon was detected by TLC to disappear, that is, the reaction ended. The temperature was lowered to 25°C, the reaction liquid was poured into 50 mL of ethyl acetate for extraction, and the organic phase was dried with anhydrous sodium sulfate. The solvent was removed by rotary evaporation, and compound 1 was obtained by sil...

Embodiment 2

[0076] This embodiment provides a triplet annihilation agent (compound 1), and its structure and preparation flow diagram are as follows:

[0077]

[0078] The synthesis method is:

[0079] Weigh 300mg 4,12-dibromo[2.2]paracyclic aromatic hydrocarbon, 107mg triphenylphosphine, 13.56mg palladium acetate and 1070mg 4,4,5,5-tetramethyl-2-(10-tert-butylperylene- Add 3-yl)-1,3,2-dioxaborolane into a 50mL reaction tube, add 12mL of dioxane, add 3mL of ultrapure water dissolved with 130mg of sodium bicarbonate, under nitrogen protection, Heating to reflux, and reacting for 30 hours, the raw material of 4,12-dibromo[2.2]p-ring aromatic hydrocarbon disappeared by TLC, that is, the reaction ended. The temperature was lowered to 25°C, the solvent was removed by rotary evaporation, the mixture was dissolved in 50 mL of dichloromethane for extraction, and the organic phase was dried over anhydrous sodium sulfate. The solvent was removed by rotary evaporation, and compound 1 was obtain...

Embodiment 3

[0083] This embodiment provides a triplet annihilation agent (compound 2), and its structure and preparation flow diagram are as follows:

[0084]

[0085] The synthesis method is:

[0086]Weigh 300mg of 4,12-dibromo[2.2]paracyclic aromatic hydrocarbon, 69mg of tricyclohexylphosphine, 9mg of palladium chloride and 674mg of [1,1':4',1"-terphenyl]-4-ylboronic acid, Add to a 50mL reaction tube, add 12mL o-xylene, add 3mL ultrapure water dissolved with 316mg sodium bicarbonate, under nitrogen protection, heat to reflux, react for 18 hours, detect 4,12-dibromo[2.2] by TLC The p-ring aromatic hydrocarbon raw material disappears, that is, the reaction is over. Lowered to 25 ° C, the mixture is dissolved in 50 mL of ethyl acetate for extraction, and the organic phase is dried with anhydrous sodium sulfate. The solvent is removed by rotary evaporation, and compound 2 is obtained by silica gel column chromatography. The rate is 91%.

[0087] The NMR data are: 1 H NMR (500MHz, Chlo...

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Abstract

The invention relates to a triplet annihilation agent as well as a preparation method and an application thereof. The triplet annihilation agent comprises a [2.2] para-cyclic aromatic hydrocarbon structure compound with a structure as shown in a formula I, wherein R is a substituted or unsubstituted group with a biphenyl structure or an acene structure. The triplet annihilation agent provided by the invention has a [2.2] para-cyclic aromatic hydrocarbon structure, and the structure contains two biphenyl or acene structures, so that the triplet annihilation agent can ensure that the triplet annihilation agent has high light-emitting quantum efficiency, can be used as an energy acceptor of a triplet annihilation up-conversion system, and can be matched with a sensitizing agent to realize photon up-conversion emission with extremely high efficiency; and the triplet annihilation agent material has great application value in the aspects of biological imaging, photocatalysis, photovoltaic solar cells, display, processing and storage of optical information and the like.

Description

technical field [0001] The invention belongs to the technical field of up-conversion materials, and relates to a triplet annihilation agent and its preparation method and application, in particular to a double chromophore triplet annihilation agent and its preparation method and application. Background technique [0002] Photon up-conversion is a technology that can convert low-energy long-wavelength light into high-energy short-wavelength light, and is an important method to improve the efficiency of solar energy utilization. The methods that can realize photon upconversion generally include rare earth material upconversion, two-photon absorption upconversion, and triplet-triplet annihilation upconversion developed in recent years. Compared with the former two, triplet-triplet annihilation upconversion requires low light intensity, high upconversion efficiency, and flexible and adjustable excitation and emission wavelengths, so triplet-triplet annihilation upconversion is w...

Claims

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Application Information

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IPC IPC(8): C07C13/70C07C1/32C07D487/22C09K11/06
CPCC07C13/70C07C1/321C07D487/22C09K11/06C09K2211/1011C09K2211/1007C09K2211/185C07C2603/92C07C2603/50C07C2603/24C07C2603/44C07C2603/52C07C2531/24Y02E10/52
Inventor 段鹏飞赵炵翰孙文静
Owner THE NAT CENT FOR NANOSCI & TECH NCNST OF CHINA
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