Compound and preparation method thereof, and triplet-triplet annihilation up-conversion system

A triplet annihilation and compound technology, applied in chemical instruments and methods, organic chemistry, luminescent materials, etc., can solve the problems of low upconversion quantum yield and high excitation threshold, so as to improve the upconversion quantum efficiency and increase the minimum triplet Effect of state exciton concentration

Inactive Publication Date: 2021-02-09
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The invention provides a compound and its preparation method and triplet-triplet annihilation upconversion system, which solves the problem that most of the upconversion systems of non-transition metal photosensitizers show low upconversion quantum yield and high excitation threshold question

Method used

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  • Compound and preparation method thereof, and triplet-triplet annihilation up-conversion system
  • Compound and preparation method thereof, and triplet-triplet annihilation up-conversion system
  • Compound and preparation method thereof, and triplet-triplet annihilation up-conversion system

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Example 1: Preparation of the compound BTZ-DMAc-2Cl with the structure represented by formula (I).

[0052] (1) intermediate: the synthesis of the compound BTZ-DMAc of the structure shown in formula (II)

[0053]

[0054] Add BTZ-Br (500mg, 2.34mmol), 9,9-dimethylacridine (DMAc, 735mg, 3.51mmol), palladium acetate (78mg, 0.35mmol) and tri-tert-butylphosphine tetrafluoro Borate (305mg, 1.05mmol), sodium tert-butoxide (808mg, 8.42mmol), and 30mL of toluene treated with water and oxygen removal were added under argon atmosphere, and reacted at 120°C for 48 hours. Cool to room temperature, pour the reaction solution into 50 mL of ice water, extract three times with dichloromethane, concentrate the organic phase, and separate by column chromatography (n-hexane:dichloromethane, v:v, 3:1) to obtain 601 mg of red powder, product rate of 75%. MS (EI) m / z: 342.12.

[0055] (2) Synthesis of BTZ-DMAc-2Cl of structure shown in formula (I)

[0056]

[0057] In a 100 mL roun...

Embodiment 2

[0058] Example 2: Preparation of the compound BTZ-2DMAc-4Cl with the structure shown in formula (I).

[0059] (1) intermediate: the synthesis of the compound BTZ-2DMAc of the structure shown in formula (II)

[0060]

[0061] Add BTZ-Br (500mg, 1.71mmol), 9,9-dimethylacridine (DMAc, 787mg, 3.76mmol), palladium acetate (57mg, 0.26mmol) and tri-tert-butylphosphine tetrafluoro Borate (223mg, 0.77mmol), sodium tert-butoxide (591mg, 6.16mmol), add 22mL of toluene treated with water and oxygen removal under argon atmosphere, and react at 120°C for 48 hours. Cool to room temperature, pour the reaction solution into 50 mL of ice water, extract three times with dichloromethane, concentrate the organic phase, and separate by column chromatography (n-hexane:dichloromethane, v:v, 2:1) to obtain 658 mg of red powder, product rate of 70%. MS (EI) m / z: 549.22.

[0062] (2) Synthesis of the compound BTZ-2DMAc-2Cl of the structure shown in formula (I)

[0063]

[0064] In a 100 mL rou...

Embodiment 3

[0065] Example 3: Preparation of the compound BTZ-DMAc-2Br with the structure shown in formula (I).

[0066] (1) intermediate: the synthesis of the compound BTDZ-DMAc of the structure shown in formula (II)

[0067]

[0068] Add BTDZ-Br (500mg, 2.32mmol), 9,9-dimethylacridine (DMAc, 728mg, 3.48mmol), palladium acetate (78mg, 0.34mmol) and tri-tert-butylphosphine tetrafluoro Borate (303mg, 1.04mmol), sodium tert-butoxide (802mg, 8.35mmol), and 30mL of toluene treated with water and oxygen removal were added under argon atmosphere, and reacted at 120°C for 48 hours. Cool to room temperature, pour the reaction solution into 50 mL of ice water, extract three times with dichloromethane, concentrate the organic phase, and separate by column chromatography (n-hexane:dichloromethane, v:v, 3:1) to obtain 574 mg of red powder, product rate of 72%. MS (EI) m / z: 343.11.

[0069] (2) Synthesis of the compound BTDZ-DMAc-2Br of the structure shown in formula (I)

[0070]

[0071] In...

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Abstract

The invention relates to the technical field of up-conversion materials, in particular to a compound and a preparation method thereof and a triplet-triplet annihilation up-conversion system. The invention discloses the compound with a structure as shown in a formula (I). The compound has a thermal activation delayed fluorescence characteristic and a heavy atom effect, and can be used as a thermally-activated delayed fluorescence material and a triplet-triplet annihilation up-conversion photosensitizer, and the heavy atom effect can significantly increase the lowest triplet exciton concentration of the photosensitizer and improve up-conversion quantum efficiency. The up-conversion photosensitizer with the structure shown in the formula (I) has visible light absorption and red light or near-infrared light emission properties and forms a triplet-triplet annihilation up-conversion system with 9,10-diphenylanthracene; and the system realizes up-conversion luminescence under the condition ofhigh excitation light power density in an organic solvent, can effectively convert green light into blue light, and has a up-conversion quantum yield of 24.4%.

Description

technical field [0001] The invention relates to the technical field of upconversion materials, in particular to a compound, a preparation method thereof and a triplet-triplet annihilation upconversion system. Background technique [0002] Up-conversion is the process of converting low-energy long-wavelength light into short-wavelength high-energy light, that is, anti-Stokes luminescence. At present, the methods to achieve upconversion generally include two-photon absorption upconversion, rare earth ion energy transfer upconversion and triplet-triplet annihilation upconversion. Compared with two-photon absorption and rare earth ion energy transfer upconversion, the triplet-triplet annihilation upconversion system can achieve higher quantum yield upconversion luminescence at a lower excitation power density, and can be used in incoherent light, It can even work under sunlight, so it has important application prospects in the fields of photocatalysis, solar power generation, a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/04C07D417/14C07D513/04C09K11/06
CPCC07D417/04C07D417/14C07D513/04C09K11/06C09K2211/1029C09K2211/1051C09K2211/1081
Inventor 刘源欧阳敏婷王姣云胡凯陈乔登
Owner GUANGDONG UNIV OF TECH
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