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Photochromic diaryl ethylene compound with up-conversion luminescence property and application thereof

A diarylethene and 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 ability, and good reversible optical switch performance

Active Publication Date: 2021-05-25
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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  • Photochromic diaryl ethylene compound with up-conversion luminescence property and application thereof
  • Photochromic diaryl ethylene compound with up-conversion luminescence property and application thereof
  • Photochromic diaryl ethylene compound with up-conversion luminescence property and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0102] Synthesis of Photochromic Diarylethene Compound DAE-1 with Upconversion Luminescent Properties

[0103] The synthetic route is:

[0104]

[0105] (1) Synthesis of Intermediate 1

[0106] 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

[0121] Synthesis of Photochromic Diarylethene Compound DAE-2 with Upconversion Luminescent Properties

[0122] The synthetic route is:

[0123]

[0124] Steps (1), (2) and (3) of this embodiment are the same as in Embodiment 1.

[0125] Synthesis of Photochromic Diarylethene Compound DAE-2 with Upconversion Luminescent Properties

[0126] 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%).

[0127] NMR and MS data of photochromic dia...

Embodiment 3

[0129] Synthesis of Photochromic Diarylethene Compound DAE-3 with Upconversion Luminescent Properties

[0130]

[0131] Steps (1), (2) and (3) of this embodiment are the same as in Embodiment 1.

[0132] 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%).

[0133] 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), 7.52-7.58...

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Abstract

The invention provides a photochromic diaryl ethylene compound with up-conversion luminescence performance and application thereof. The photochromic diaryl ethylene compound has a structure as shown in a formula I in the specification. The photochromic diaryl ethylene compound is a switching type single-photon absorption up-conversion luminescent material, can realize up-conversion luminescence of high-vibration energy level absorption, and can realize the switching effect of up-conversion luminescence through regulation and control of light with multiple wavelengths. Due to the fact that light with a long wavelength has a high tissue penetrating power, the photochromic diaryl ethylene compound can also effectively eliminate background noise such as auto-fluorescence, and is expected to be applied to a super-resolution single-photon imaging system.

Description

technical field [0001] The invention belongs to the field of luminescent materials, and in particular relates to a photochromic diarylethene compound with upconversion luminescent 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 a...

Claims

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Application Information

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Patent Type & Authority Applications(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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