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Organic luminogens

A technology of groups and compounds, applied in the field of organic luminophores

Active Publication Date: 2019-11-15
THE HONG KONG UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the development of OSMWLEs or single molecules with two suitable luminescences faced many challenges in the past

Method used

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  • Organic luminogens
  • Organic luminogens
  • Organic luminogens

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0156] Synthesis and Characterization of TriPO-N

[0157] An exemplary reaction scheme for preparing TriPO-N is as follows:

[0158]

[0159] Synthesis of compound 2

[0160] Benzoyl chloride (0.82 mL, 7.00 mmol) was added to a solution of compound 1 (1.00 g, 4.73 mmol) and pyridine (1.11 mL, 14.10 mmol) in 1,2-dichloroethane (30 mL), and Medium reflux for 12h. The reaction mixture was cooled to room temperature and washed with Na 2 CO 3 solution (3 x 30 mL) was washed. The organic layer was dried over anhydrous sodium sulfate. After solvent evaporation in vacuo, the residue was purified by flash column chromatography with hexane / EA (20:1, v / v) to give 2 as a white solid (1.10 g, 74%). 1 H NMR (400MHz, CDCl 3 )δ8.01(d, J=7.3Hz, 2H), 7.59(t, J=7.4Hz, 1H), 7.48(t, J=7.6Hz, 2H), 7.41(d, J=7.0Hz, 2H) ,7.28–7.09(m,8H),5.35(s,2H). 13 C NMR (100MHz, CDCl 3 )δ 192.86, 170.12, 143.42, 134.67, 134.52, 133.03, 129.21, 128.47, 128.27, 128.16, 127.41, 127.12, 126.93, 126.1...

Embodiment 2

[0165] Synthesis and Characterization of TPO

[0166] An exemplary reaction scheme for preparing TPO is as follows:

[0167]

[0168] Synthesis of Compound 4a

[0169] To a solution of compound 3a (2.12 g, 10.00 mmol) and aniline (1.12 g, 12 mmol) in toluene / ethanol (toluene / ethanol=10:1, 40 mL) was added 10 drops of concentrated HCl. The reaction mixture was stirred and refluxed for 12h. After the reaction mixture was cooled to room temperature, the precipitate was filtered in vacuo. The solid was added to ethyl acetate and K 2 CO 3 in solution. The aqueous phase was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by flash column chromatography with hexane / EA (10:1 to 2:1, v / v) to afford the desired compound 4a (2.41 g, 84%) as a bright white solid. 1 H NMR (400MHz, MeOD) δ8.05(d, J=7.5Hz, 2H), 7.53(t, J=7.1Hz, 1H), 7.49–7.37(...

Embodiment 3

[0176] 1Synthesis and characterization of MOTPO

[0177] An exemplary reaction scheme for the preparation of 1MOTPO is as follows:

[0178]

[0179] Synthesis of compound 4b

[0180] To a solution of compound 3a (2.12 g, 10.00 mmol) and 4-methoxyaniline (1.48 g, 12 mmol) in toluene / ethanol (toluene / ethanol=10:1, 40 mL) was added 10 drops of concentrated HCl. The reaction mixture was stirred and refluxed for 12h. After the reaction mixture was cooled to room temperature, the precipitate was filtered in vacuo. The solid was added to ethyl acetate and K 2 CO 3 in solution. The aqueous phase was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by flash column chromatography with hexane / EA (10:1 to 2:1, v / v) to afford the desired compound 4b (2.54 g, 80%) as a bright white solid. 1 H NMR (400MHz, acetone) δ8.14–8.08(m,2H),7.56–7.49(m...

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Abstract

The invention relates to small molecule compounds having aggregation-induced emission (AIE) characteristics. The compounds include organic, aromatic salts having anion-pai+ interactions. In some embodiments, the anion-pai+ interactions can include heavy-atom-anion- pai+ interactions. The heavy atom anions can include bromine or iodide, for example. The compounds can be water-soluble. The compoundscan be useful as probes for bioimaging, as room temperature luminogens for electroluminescent devices, and white organic light-emitting applications.

Description

technical field [0001] The subject matter generally relates to a series of compounds with aggregation-induced luminescent properties and their use in bioimaging, electroluminescent devices and / or 3D printing. Background technique [0002] Organic luminophores are useful in a variety of applications including, for example, electroluminescent devices, optoelectronic devices, chemical sensors, and biosensors. However, the application of traditional organic luminophores is greatly limited by the aggregation-induced quenching (ACQ) effect. Traditional organic luminophores have strong luminescence in dilute solutions, but weak or even no luminescence in high-concentration solutions during aggregation or in solid state. Because the ACQ effect is unfavorable for practical applications, many steps have been taken to avoid the aggregation of conventional luminophores, including chemical reactions, physical methods, and / or engineering processes. Unfortunately, these methods have limi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/30C07D263/32C07D403/12C07F15/00C07F19/00C09K11/07H01L51/50
CPCC07D263/32C09K11/06C09K11/07C07D233/58C07D277/22H10K85/656H10K85/6565H10K85/654H10K50/11H10K2101/10A01N43/76C09K2211/1018G01N21/6486
Inventor 唐本忠王建国顾星桂张鹏飞
Owner THE HONG KONG UNIV OF SCI & TECH
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