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9,10-diphenyl anthracene derivative as reactive luminescent agent, preparation method thereof and high-efficiency weak light up-conversion system prepared from reactive luminescent agent 9,10-diphenyl anthracene derivative

A diphenylanthracene and luminescent agent technology, applied in the field of photon frequency upconversion, can solve the problems of limiting weak light upconversion, unfavorable molecular modification and polymerization, and the upconversion efficiency has not yet exceeded DPA.

Active Publication Date: 2018-12-14
SUZHOU UNIV OF SCI & TECH
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  • Abstract
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AI Technical Summary

Problems solved by technology

In order to further improve the upconversion efficiency, our research group has designed a series of DPA derivatives, such as connecting naphthalene ring, thiophene ring or furan at the 9,10-position of anthracycline; atoms and methyl groups; even modified by anthracycline 9,10-position multi-branching, however, the upconversion efficiencies obtained by these new luminescent agents have not yet surpassed DPA, which makes DPA molecules the current green-to-blue upconversion The star luminescent agent in the material
However, there is no active site in the molecular structure of 9,10-diphenylanthracene (DPA), which is not conducive to further modification and polymerization of the molecule, thus limiting the application of weak light upconversion

Method used

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  • 9,10-diphenyl anthracene derivative as reactive luminescent agent, preparation method thereof and high-efficiency weak light up-conversion system prepared from reactive luminescent agent 9,10-diphenyl anthracene derivative
  • 9,10-diphenyl anthracene derivative as reactive luminescent agent, preparation method thereof and high-efficiency weak light up-conversion system prepared from reactive luminescent agent 9,10-diphenyl anthracene derivative
  • 9,10-diphenyl anthracene derivative as reactive luminescent agent, preparation method thereof and high-efficiency weak light up-conversion system prepared from reactive luminescent agent 9,10-diphenyl anthracene derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] Add 2-formylphenylboronic acid (5.63 g, 2.5 equiv, 37.5 mmol) and 9,10-dibromoanthracene (5.05 g, 1 equiv, 15 mmol) in 120 mL toluene and 24 mL ethanol to a 250 mL three-necked flask, and K 2 CO 3 (9.84 g, 69mmol) was dissolved in 48mL of distilled water and mixed into the above solution. Argon was then bubbled into the mixed solution for 15 minutes, followed by the addition of tetrakis(triphenylphosphine) palladium (0) (0.39 g, 1.2 mmol), and then argon was bubbled in for 5 minutes, and heated to reflux in an argon atmosphere to react During the process, the progress of the reaction was tracked by spotting the plate. The developer was dichloromethane / petroleum ether at a ratio of 1:1. After 48 hours, the spot of the raw material 9,10-dibromoanthracene almost disappeared, and the reaction was stopped.

[0058] After the reaction was over, the reaction solution was distilled under reduced pressure to obtain a black solid mixture, and the organic phase was extracted and...

Embodiment 2

[0065] The reaction solution of Example 1 was distilled under reduced pressure to obtain a black solid mixture, and the organic phase was extracted and separated by dichloromethane and saturated brine several times, and anhydrous Na was added 2 SO 4 After removing water, use column chromatography to separate the product, the developer used is dichloromethane 2:petroleum ether 3, and then undergo secondary purification by recrystallization to obtain a light yellow powder, which is cis 9,10-(2-formyl ) phenylanthracene, hereinafter referred to as cis-o - FDPA, 2.62 g (6.8 mmol), 45.4% yield.

[0066] Melting point: 311.1-312.6°C.

[0067] Mass spectrometry (ESI: m / z ): Calculated 386.13, found 387.14 [M+H] +

[0068] 1 H NMR (400 MHz, DMSO- d 6 ) δ 7.35 – 7.55 (m, 8H), 7.57 – 7.71 (d, J = 7.3Hz, 2H), 7.79 – 7.93 (t, J = 7.4 Hz, 2H), 7.93 – 8.10 (s, 2H), 8.12 – 8.29(d, J = 7.8 Hz, 2H), 9.31 – 9.46 (d, J = 3.3 Hz, 2H).

[0069] The molecular structural formula o...

Embodiment 3

[0072] Add 3-formylphenylboronic acid (2.82 g, 2.5 equiv, 18.8 mmol), 9,10-dibromoanthracene (2.53 g, 1 equiv, 7.5 mmol) in 60 mL toluene and 12 mL ethanol into a 150 mL three-necked flask, and K 2 CO 3 (5.92 g, 34.5 mmol) was dissolved in 23 mL of distilled water and mixed into the above solution. Argon was then bubbled into the mixed solution for 15 minutes, followed by the addition of tetrakis(triphenylphosphine) palladium (0) (0.25 g, 0.82 mmol), and then argon was bubbled in for 5 minutes, then heated to reflux in an argon atmosphere, and the reaction During the process, the progress of the reaction was tracked by spotting the plate. The developer was dichloromethane 3: petroleum ether 4. The reaction lasted for 48 hours, and the spots of the raw material 9,10-dibromoanthracene almost disappeared, so the reaction was stopped.

[0073] After the reaction was over, the reaction solution was distilled under reduced pressure to obtain a black solid mixture, and the organic...

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Abstract

The invention discloses a 9,10-diphenyl anthracene derivative as reactive luminescent agent, a preparation method thereof and a high-efficiency weak light upconversion system prepared from the reactive luminescent agent 9,10-diphenyl anthracene derivative. Reactive upconversion luminescent agents are obtained by introducing reactive groups (such as benzaldehyde and decyl alcohol) into the 9,10-position of the anthracene ring; meanwhile, by introducing an aldehyde group and hydroxyl formaldehyde into different positions (such as ortho-, meta-, and para-), energy level difference (DEST) of singlet state (ES) and triplet state (ET) of the reactive luminescent agent is changed, and a plurality of novel luminescent agents with higher upconversion efficiency than that of a current star luminescent agent DPA are obtained. The luminescent agent has selective upconversion response characteristic to solvent polarity, and the upconversion efficiency obtained by a binary system prepared from the luminescent agent and a photosensitizer exceeds the highest value reported in the prior art.

Description

technical field [0001] The invention belongs to the technical field of photon frequency up-conversion, and specifically relates to a class of singlet / triplet energy level difference (∆E ST ) triplet annihilation agent as a reactive luminescent agent in a green-to-blue weak-light up-conversion system has high-efficiency weak-light up-conversion efficiency, including its preparation method and its application as a luminescent agent in a high-efficiency weak-light up-conversion system. Background technique [0002] Optical frequency up-conversion is to convert long-wave light waves into short-wavelength light waves to achieve frequency up-conversion. At present, there are two main types of optical frequency upconversion technologies through organic materials: one is the upconversion by the two-photon absorption mechanism (TPA-UC for short, or Two-photon absorption upconversion), and the other is the upconversion by the triplet annihilation mechanism. (TTA-UC for short, namely ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C47/546C07C45/68C07C29/14C07C33/26C09K11/06
CPCC07C33/26C07C47/546C09K11/06C09K2211/1007C09K2211/1011
Inventor 王筱梅谢先格于雪叶常青陈佳宋飒飒何秋实
Owner SUZHOU UNIV OF SCI & TECH
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