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Annihilation agent applied to triplet-triplet annihilation upconversion system and its preparation and application method

A technology of triplet annihilation and triplet state, applied in chemical instruments and methods, condensation between hydrocarbons and non-hydrocarbons, organic chemistry, etc., can solve the problems of low fluorescence quantum yield, few types of annihilation agents, and difficult preparations, etc. problems, to achieve the effect of efficient and stable preparation, no pollution in the preparation process, and easy-to-obtain preparation raw materials

Inactive Publication Date: 2019-07-19
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 upconversion system and its preparation and application method
  • Annihilation agent applied to triplet-triplet annihilation upconversion system and its preparation and application method
  • Annihilation agent applied to triplet-triplet annihilation upconversion system and its preparation and application method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

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

[0031] Respectively, 5mmol of phenylboronic acid, 5mmol of bromobenzaldehyde and 5mmol of K 2 CO 3 Add to 12ml of DMF / H2O solution, stir for 2min and add 5mol% Pd(OAc)2 after fully dissolved, fill with nitrogen protection, stir at 25°C, stop the reaction for 5h, add 50ml of acetic acid to the solution, and wash the 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.

[0032] Add 10mmol 2-formyl biphenyl and 5mmol anthracene into a 250ml single-necked flask equipped with 100ml dichloroethane, stir while adding 10mmol acetic anhydride, drop 0.5mmol trifluoromethanesulfonic acid, stir at 25°C, TLC (developed Petroleum ether:ethyl acetate=30:1) detect the end of the reaction...

Embodiment 2

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

[0042] Respectively, 5mmol of phenylboronic acid, 5mmol of bromobenzaldehyde and 5mmol of K 2 CO 3 Add to 12ml of DMF / H2O solution, stir for 2min and add 5mol% Pd(OAc)2 after fully dissolved, fill with nitrogen protection, stir at 25°C, stop the reaction for 8h, add 50ml of acetic acid to the solution, and wash the 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.

[0043] Add 10mmol 2-formyl biphenyl and 5mmol anthracene into a 250ml single-necked flask equipped with 100ml dichloroethane, stir while adding 10mmol acetic anhydride, drop 0.5mmol trifluoromethanesulfonic acid, stir at 25°C, TLC (developed Petroleum ether:ethyl acetate=30:1) detect the end of the reaction...

Embodiment 3

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

[0046] Respectively, 5mmol of phenylboronic acid, 5mmol of bromobenzaldehyde and 5mmol of K 2 CO 3 Add it into 12ml DMF / H2O solution, stir for 2min and add 5mol% Pd(OAc)2 after it is fully dissolved, fill it with nitrogen protection, stir at 25°C, stop the reaction for 12h, add 50ml acetic acid to the solution, and wash the acetic acid 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-formyl biphenyl and 5mmol anthracene into a 250ml single-necked flask equipped with 100ml dichloroethane, stir while adding 10mmol acetic anhydride, drop 0.5mmol trifluoromethanesulfonic acid, stir at 25°C, TLC (developed Petroleum ether:ethyl acetate=30:1) detect the end of the rea...

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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 present invention relates to the field of organic upconversion. It specifically relates to an efficient and stable up-conversion system annihilation agent and its preparation method and application in up-conversion, including a new type of small molecule annihilation agent 9,10-difluorenyl anthracene. Background technique [0002] Up-conversion is a technology that converts low-energy (long-wavelength) light into high-energy (short-wavelength) light through a multi-photon mechanism. The potential application value has attracted extensive attention. At present, there are many technologies for realizing up-conversion, such as using dyes with large two-photon absorption cross section to realize two-photon up-conversion, or using rare earth materials to realize up-conversion of light wave frequency, etc. In recent years, the up-conversion technology based on triplet-triplet annihilation (TTA) has low excitation light energy (which can be realized by ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C2/86C07C15/60C09K11/06C09K9/02
CPCY02P20/52
Inventor 李祥高贾异尤静王世荣肖殷
Owner TIANJIN UNIV
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