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Annihilation agent applied to triplet-triplet annihilation up-conversion system, and preparation and application methods thereof

A technology of triplet annihilation and triplet state, which is applied in the preparation of organic compounds, carbon-based compounds, chemical instruments and methods, etc., can solve the problems of low fluorescence quantum yield, few types of annihilation agents, poor stability, etc., and achieve Efficient and stable preparation, pollution-free preparation process, and high stability

Inactive Publication Date: 2017-01-25
TIANJIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The currently reported annihilation agents have fewer types, are difficult to prepare, and their fluorescence quantum yield is not high, and their stability in air is poor.

Method used

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  • Annihilation agent applied to triplet-triplet annihilation up-conversion system, and preparation and application methods thereof
  • Annihilation agent applied to triplet-triplet annihilation up-conversion system, and preparation and application methods thereof
  • Annihilation agent applied to triplet-triplet annihilation up-conversion system, and preparation and application methods thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Synthesis of 9,10-difluorenylanthracene (DFA).

[0031] Respectively mix 5mmol of phenylboronic acid, 5mmol of pro-bromobenzaldehyde and 5mmol of K 2 CO 3 Add to 12ml DMF / H2O solution, stir for 2min until fully dissolved, add 5mol% Pd(OAc)2, fill with nitrogen protection, stir at 25℃, reaction stop for 5h, add 50ml acetic acid to the solution, wash ethyl acetate with water The ester was extracted 3 times, dried with anhydrous magnesium sulfate, and rotary evaporated under reduced pressure to obtain a crude product, which was purified by column chromatography (silica gel, petroleum ether: ethyl acetate 50:1) to obtain a colorless liquid product.

[0032] Add 10mmol 2-aldehyde biphenyl and 5mmol anthracene into a 250ml single-neck flask filled with 100ml dichloroethane, add 10mmol acetic anhydride while stirring, add 0.5mmol trifluoromethanesulfonic acid dropwise, stir at 25℃, TLC (expanded Petroleum ether: ethyl acetate=30:1) It is detected that the reaction is over. It was ...

Embodiment 2

[0041] Synthesis of 9,10-difluorenylanthracene (DFA).

[0042] Respectively mix 5mmol of phenylboronic acid, 5mmol of pro-bromobenzaldehyde and 5mmol of K 2 CO 3 Add to 12ml DMF / H2O solution, stir for 2min to fully dissolve, add 5mol% Pd(OAc)2, fill with nitrogen protection, stir at 25℃, and stop the reaction for 8h, add 50ml acetic acid to the solution, wash ethyl acetate with water The ester was extracted 3 times, dried with anhydrous magnesium sulfate, and rotary evaporated under reduced pressure to obtain a crude product, which was purified by column chromatography (silica gel, petroleum ether: ethyl acetate 50:1) to obtain a colorless liquid product.

[0043] Add 10mmol 2-aldehyde biphenyl and 5mmol anthracene into a 250ml single-neck flask filled with 100ml dichloroethane, add 10mmol acetic anhydride while stirring, add 0.5mmol trifluoromethanesulfonic acid dropwise, stir at 25℃, TLC (expanded Petroleum ether: ethyl acetate=30:1) It is detected that the reaction is over. It ...

Embodiment 3

[0045] Synthesis of 9,10-difluorenylanthracene (DFA).

[0046] Respectively mix 5mmol of phenylboronic acid, 5mmol of pro-bromobenzaldehyde and 5mmol of K 2 CO 3 Add to 12ml DMF / H2O solution, stir for 2min to fully dissolve, add 5mol% Pd(OAc)2, fill with nitrogen protection, stir at 25℃, reaction stop for 12h, add 50ml acetic acid to the solution, wash ethyl acetate with water The ester was extracted three times, dried with anhydrous magnesium sulfate, and rotary evaporated under reduced pressure to obtain a crude product, which was purified by column chromatography (silica gel, petroleum ether: ethyl acetate 50:1) to obtain a colorless liquid product.

[0047] Add 10mmol 2-aldehyde biphenyl and 5mmol anthracene into a 250ml single-neck flask filled with 100ml dichloroethane, add 10mmol acetic anhydride while stirring, add 0.5mmol trifluoromethanesulfonic acid dropwise, stir at 25℃, TLC (expanded Petroleum ether: ethyl acetate=30:1) It is detected that the reaction is over. It was...

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Abstract

The invention relates to an annihilation agent applied to a triplet-triplet annihilation up-conversion system, and a preparation method and an application method thereof. The annihilation agent is 9,10-difluorenyl anthracene. The preparation method includes: generating an intermediate product by using Suzuki reaction, and then substituting 9, 10 positions of anthracene with the intermediate product by using carbanion reaction. A photosensitizer of the annihilation agent on the triplet-triplet annihilation up-conversion system is a metalloporphyrin compound: octaethylporphyrin palladium. The up-conversion system converts green light of 532nm into blue light of 440nm, and conversation rate of the up-conversion system is 5.86%. The disclosed small organic molecule annihilation agent material easy to prepare and efficient and stable is prepared through raw material easy and simple to obtain, uses the preparation process simple and free from pollution, conforms to development requirements of green chemistry, and is suitable for industrial mass production.

Description

Technical field [0001] The invention relates to the field of organic upconversion. Specifically, it relates to a high-efficiency and stable up-conversion system annihilator and its preparation method and application in up-conversion, including a novel small molecule annihilator 9,10-difluorenylanthracene. Background technique [0002] Upconversion is a technology that converts low-energy (long-wavelength) light into high-energy (short-wavelength) light through a multiphoton mechanism. It is used in solar cells, artificial photosynthesis, photocatalysis, and optoelectronic devices. The potential application value has received widespread attention. At present, there are many technologies for up-conversion, such as using dyes with larger two-photon absorption cross-sections to achieve two-photon up-conversion, or using rare earth materials to achieve up-conversion of lightwave frequencies. In recent years, the up-conversion technology based on triplet-triplet annihilation (TTA) re...

Claims

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Application Information

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IPC IPC(8): C07C2/86C07C15/60C09K11/06C09K9/02
CPCY02P20/52C07C2/867C07C45/68C09K9/02C09K11/06C07C15/60C07C47/546
Inventor 李祥高贾异尤静王世荣肖殷
Owner TIANJIN UNIV
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