A kind of photochromic diarylethene compound with up-conversion luminescence properties and its application

A diarylethene, photochromic technology, applied in organic chemistry, color-changing fluorescent materials, chemical instruments and methods, etc., to achieve the effect of eliminating background noise, strong tissue penetration, and good reversible optical switching performance

Active Publication Date: 2022-05-03
THE NAT CENT FOR NANOSCI & TECH NCNST OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Thus limiting the application of such up-conversion materials

Method used

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  • A kind of photochromic diarylethene compound with up-conversion luminescence properties and its application
  • A kind of photochromic diarylethene compound with up-conversion luminescence properties and its application
  • A kind of photochromic diarylethene compound with up-conversion luminescence properties and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0101] Synthesis of Photochromic Diarylethene Compound DAE-1 with Upconversion Luminescence Properties

[0102] The synthetic route is:

[0103]

[0104] (1) Synthesis of Intermediate 1

[0105] Under an argon atmosphere, slowly add n-butyllithium hexane solution (53mL, 1.6M) dropwise into a tetrahydrofuran solution (100mL) containing benzothiophene (10g, 75mmol) at -78°C. The reaction was continued at °C for 1 h, then ethyl bromide (3.2 mL, 84 mmol) was slowly added dropwise at -78 °C. After dropping, slowly return to room temperature, and continue to react for 12h. After the reaction was complete, add saturated aqueous sodium chloride solution (50mL) to quench the reaction, remove the solvent under reduced pressure, then add saturated aqueous sodium chloride solution (100mL), extract with petroleum ether (100mL), use sodium sulfate to dry the organic phase, spin off Solvent, using petroleum ether for column chromatography, isolated intermediate 1 (11 g, yield 82%).

...

Embodiment 2

[0120] Synthesis of Photochromic Diarylethene Compound DAE-2 with Upconversion Luminescence Properties

[0121] The synthetic route is:

[0122]

[0123] Steps (1), (2) and (3) of this embodiment are the same as in Embodiment 1.

[0124] Synthesis of Photochromic Diarylethene Compound DAE-2 with Upconversion Luminescence Properties

[0125] Weigh intermediate 4 (1.72g), 4-(2-bromoethoxy)phenylboronic acid (0.5g), potassium carbonate (0.6g), Pd 2 (dba) 3 (0.3g) was dissolved in dioxane (10mL), tricyclohexylphosphonium toluene solution (0.8mL, 18wt%) was added, refluxed under argon atmosphere for 12h, cooled to room temperature after the reaction was completed, the solvent was rotated, extracted with chloroform , dry the organic phase with sodium sulfate, spin off the solvent and perform column chromatography (developing solvent: petroleum ether / ethyl acetate volume ratio = 20:1) to obtain a light yellow solid (0.15g, yield 83%).

[0126] NMR and MS data of photochromic d...

Embodiment 3

[0128] Synthesis of Photochromic Diarylethene Compound DAE-3 with Upconversion Luminescence Properties

[0129]

[0130] Steps (1), (2) and (3) of this embodiment are the same as in Embodiment 1.

[0131] Weigh intermediate 4 (0.86g), thienothiophene boronic acid (0.4g), potassium carbonate (0.4g), Pd 2 (dba) 3 (0.2g) was dissolved in dioxane (10mL), tricyclohexylphosphonium toluene solution (0.4mL, 18wt%) was added, refluxed for 4h under argon atmosphere, cooled to room temperature after the reaction was completed, the solvent was spun off, and extracted with chloroform , dry the organic phase with sodium sulfate, spin off the solvent and perform column chromatography (developing solvent: petroleum ether / ethyl acetate volume ratio = 20:1) to obtain an orange solid (0.3 g, yield 70%).

[0132] NMR and MS data of photochromic diarylethene compound DAE-3 with upconversion luminescence properties: 1 HNMR (400MHz, chloroform-d) δ7.85-7.92(m, 2H), 7.74-7.76(m, 1.3H), 7.52-7.5...

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Abstract

The invention provides a photochromic diarylethene compound with upconversion luminescence performance and application thereof. The photochromic diarylene compound has the structure shown in formula I. The photochromic diarylethene compound of the present invention is a type of switch-type single-photon absorption up-conversion luminescent material, which can realize up-conversion luminescence with high vibration energy level absorption, and can realize up-conversion luminescence through multiple wavelength light regulation Due to the strong tissue penetration ability of long wavelength, the photochromic diarylethene compound can also effectively eliminate background noise such as autofluorescence, which is expected to be applied in super-resolution single-photon imaging systems.

Description

technical field [0001] The invention belongs to the field of luminescent materials, and in particular relates to a photochromic diarylethene compound with up-conversion luminescence performance and an application thereof. Background technique [0002] Up-conversion luminescent materials can convert low-energy long-wavelength light into high-energy short-wavelength light. The methods that can achieve photon upconversion generally include two-photon absorption upconversion, rare earth material upconversion, and triplet-triplet annihilation upconversion developed in recent years. In addition, there is another way of upconversion, single photon upconversion. Absorption upconversion (phonon-assisted upconversion), although this type of material is relatively less studied. However, single-photon absorption upconversion has multiple advantages: firstly, no oxygen removal is required, secondly, low light intensity is required, thirdly, high upconversion efficiency and single-photon...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D333/54C07D495/04C07D519/00C09K9/02
CPCC07D333/54C07D519/00C07D495/04C09K9/02C09K2211/1092C09K2211/1007
Inventor 段鹏飞韩建雷
Owner THE NAT CENT FOR NANOSCI & TECH NCNST OF CHINA
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