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Phenanthroimidazole derivative with ESIPT (excited-state intramolecular proton transfer) and AIE (aggregation-induced emission) properties and preparation method and application thereof

A technology of phenanthroimidazole and derivatives, which is applied to phenanthroimidazole derivatives with ESIPT and AIE properties and their preparation and application fields, can solve problems such as low emission efficiency and concentration quenching

Active Publication Date: 2019-01-04
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But ESIPT also has disadvantages, such as low emission efficiency, concentration quenching phenomenon

Method used

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  • Phenanthroimidazole derivative with ESIPT (excited-state intramolecular proton transfer) and AIE (aggregation-induced emission) properties and preparation method and application thereof
  • Phenanthroimidazole derivative with ESIPT (excited-state intramolecular proton transfer) and AIE (aggregation-induced emission) properties and preparation method and application thereof
  • Phenanthroimidazole derivative with ESIPT (excited-state intramolecular proton transfer) and AIE (aggregation-induced emission) properties and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Example 1 Synthesis of 4,4,5,5-tetramethyl-2-(1,2,2-triphenylethenyl)-1,3,2-dioxaborolane (VI)

[0037] Under nitrogen protection, 2-bromo-1,1,2-triphenylethylene (1.0 g, 3 mmol) represented by formula (IV) was dissolved in anhydrous tetrahydrofuran (20 mL) solvent, and 1.6M n-BuLi (3.0 mL, 7.5 mmol) was stirred for 1 h. Then isopropanol pinacol borate (2.15 mL, 10.7 mmol) represented by formula (V) was slowly added, and the system was heated to room temperature and reacted overnight. After the reaction was completed, the reaction was quenched with saturated aqueous ammonium chloride, extracted with deionized water and dichloromethane, and the obtained organic phase was added with anhydrous MgSO 4 After drying, concentrate under reduced pressure, and then separate and purify by column chromatography. The stationary phase is 300-400 mesh silica gel, and the mobile phase is a mixed solvent of petroleum ether / ethyl acetate (volume ratio 50:1). solution, the solvent was e...

Embodiment 2

[0039] Example 2 Synthesis of 5-bromo-2-(1-phenyl-1H-phenanthrene[9,10-d]imidazol-2-yl)phenol (VII-a)

[0040]Under nitrogen protection, 9,10-phenanthrenequinone (0.57g, 2.74mmol) represented by formula (II), 4-bromo-2-hydroxybenzaldehyde (0.5g, 2.5mmol) represented by formula (III-a), Ammonium acetate (0.96mg, 12.5mmol) was added to a 100mL two-necked flask, aniline (0.3mg, 3mmol) and 30mL of acetic acid were added, the temperature was raised to 120°C, and the reaction was carried out for 12h. After the reaction, cool the system to room temperature, add water and dichloromethane for extraction, combine the organic phases, dry overnight with anhydrous magnesium sulfate, remove the desiccant by suction filtration, evaporate the solvent under reduced pressure, add dichloromethane again to dissolve, Add crude silica gel to mix the sample, and pass through the column by chromatography. The eluent is a mixed solvent of petroleum ether and dichloromethane (volume ratio, 2:1), and fi...

Embodiment 3

[0042] Example 3 Synthesis of 4-bromo-2-(1-phenyl-1H-phenanthrene[9,10-d]imidazol-2-yl)phenol (VII-b)

[0043] The synthetic method is the same as Example 2, and the difference is that 4-bromo-2-hydroxybenzaldehyde shown in formula (III-a) is replaced by 5-bromosalicylaldehyde (201.02g / mol, 2.5mmol, 0.5g), the light yellow target product (VII-b) 1.02g was finally obtained, and the yield was 93%.

[0044] MS (ESI) characterization of 4-bromo-2-(1-phenyl-1H-phenanthrene[9,10-d]imidazol-2-yl)phenol found to be 466.2.

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Abstract

The invention provides a phenanthroimidazole derivative with ESIPT (excited-state intramolecular proton transfer) and AIE (aggregation-induced emission) properties, shown as formula (I-a) or (I-b) which is shown in the description, and a preparation method and application thereof. The phenanthroimidazole derivative synthesized by the preparation method has both ESIPT and AIE effects. The phenanthroimidazole derivative herein is suitable for fluorine ion detection and is a potential fluorescence sensor material.

Description

(1) Technical field [0001] The invention relates to a phenanthroimidazole derivative with ESIPT and AIE properties, a preparation method thereof, and an application of the phenanthroimidazole derivative as a fluoride ion fluorescence detector. (2) Background technology [0002] Organic light-emitting materials have attracted extensive attention from researchers around the world in a large number of cutting-edge scientific fields such as third-generation display technology, photodynamic therapy, and fluorescent sensors. Among them, the luminescent material system with both Excited-State Intramolecular Proton Transfer (ESIPT) and Aggregation-induced emission (AIE) properties has made significant research progress. [0003] ESIPT refers to the fact that organic compound molecules absorb energy under the action of light, heat or electricity, and transition from the ground state to the excited state, and the hydrogen protons in the molecule will be transferred to the adjacent N, ...

Claims

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Application Information

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IPC IPC(8): C07D235/02C09K11/06G01N21/64
CPCC07D235/02C09K11/06C09K2211/1044G01N21/643G01N2021/6432
Inventor 董玉杰沈俊杰宋庆宝
Owner ZHEJIANG UNIV OF TECH
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