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Red light emitting material based on excited state proton transfer and preparation method and application thereof

A technology of proton transfer and luminescent materials, applied in luminescent materials, nanotechnology for materials and surface science, material excitation analysis, etc., can solve the problems of complex manufacturing process, high cost, poor stability, etc., and achieve high decomposition temperature, High thermal sensitivity and good thermal stability

Pending Publication Date: 2022-08-09
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] Technical problem to be solved: In order to overcome the deficiencies in the prior art, this application proposes a red-light material based on excited state proton transfer and its preparation method and application, in order to solve the complex manufacturing process, high cost and poor stability in the prior art And other issues

Method used

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  • Red light emitting material based on excited state proton transfer and preparation method and application thereof
  • Red light emitting material based on excited state proton transfer and preparation method and application thereof
  • Red light emitting material based on excited state proton transfer and preparation method and application thereof

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preparation example Construction

[0047] The preparation method based on the excited state proton transfer red light material comprises the following steps:

[0048] The first step: take intermediate 3-(benzo[d]thiazol-2-yl)-2-hydroxy-5-methyl-benzaldehyde (HBT-CHO) (0.50g, 1.86mmol) and intermediate 2, 2-Difluoro-4-methyl-6-phenyl-2(1H)-dioxaborane (DMBF 2 ) (0.47g, 2.23mmol) was mixed and added into a 100mL three-necked round-bottomed flask, and a double-row pipe was used to evacuate, blow nitrogen three times, and insert a nitrogen ball;

[0049] The second step: use a syringe to add piperidine (0.16g, 1.86mmol) under nitrogen environment, then add 40mL solvent absolute ethanol with a syringe; Bubble nitrogen for 30 minutes, put the reaction device into the oil bath, and the liquid level in the bottle Slightly higher than the liquid level of the oil bath, heating and refluxing for 12 hours;

[0050] The third step: after the reaction is completed, cool to room temperature, use a rotary evaporator to spin ...

Embodiment 1

[0054] A preparation method for preparing nanoparticles based on excited state proton transfer red light material in an aqueous solution or a PBS solution, specifically comprising the following steps:

[0055] The first step: transfer 1 mg of HBT-BF based on the excited state proton transfer red light material 2 Dissolve in 1mL THF to make a 1mg / mL solution;

[0056] The second step: under 1440W ultrasonic conditions, inject 1 mL of the solution into 10 mL of deionized water or PBS solution, and remove the tetrahydrofuran in the mixed solution by bubbling nitrogen;

[0057] The third step: heating and concentrating the prepared solution under a nitrogen atmosphere at 90 °C, and then filtering with a 0.2 μm filter; HBT-BF can be obtained 2 Nanoparticles in water or PBS solution.

Embodiment 2

[0059] A red light material based on excited state proton transfer and a non-energy transfer temperature-resistant diphenyl(6-(pyrrolidin-1-yl)pyrene-1-yl)phosphine oxide doped in PBS solution was prepared. The preparation method of nanoparticle specifically comprises the following steps:

[0060] Step 1: Weigh the excited state proton transfer red light material HBT-BF 2 Dissolve 1 mg of diphenyl(6-(pyrrolidin-1-yl)pyrene-1-yl)phosphine oxide and temperature-resistant fluorescent material diphenyl(6-(pyrrolidin-1-yl)pyrene-1-yl)phosphine oxide in 1 mL of THF respectively to make a 1 mg / mL solution;

[0061] The second step: proportioning the two solutions prepared by mass fractions of diphenyl (6-(pyrrolidin-1-yl)pyrene-1-yl)phosphine oxide: HBT-BF 2 = 1:3 ratio mixing, with 1440W ultrasonic mixing;

[0062] The third step: under 1440W ultrasonic conditions, inject 1mL of the mixed solution into 10mL of deionized water or PBS solution, and remove the tetrahydrofuran in the ...

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Abstract

The invention discloses a red light emitting material based on excited state proton transfer as well as a preparation method and application of the red light emitting material. An organic boron difluoride complex containing excited state intramolecular proton transfer is prepared and synthesized. The temperature sensing property of the material in an organic solvent diethylene glycol dimethyl ether (MOE) is studied, and the monochromatic temperature sensing property of the material in an aqueous solution and a phosphate (PBS) buffer solution is further studied. The material is doped with temperature-resistant diphenyl (6-(pyrrolidine-1-yl) pyrene-1-yl) phosphine oxide to prepare a non-energy-transfer ratio-type organic fluorescence thermometer, the non-energy-transfer ratio-type organic fluorescence thermometer has excellent sensing characteristics, and temperature indication can be carried out by virtue of fluorescence color change observed by naked eyes. The material disclosed by the invention is simple to prepare, low in price and high in yield. The organic fluorescent temperature sensing probe prepared from the material has high temperature resolution and sensitivity in a wide temperature range, and has very high application value.

Description

technical field [0001] The invention belongs to the technical field of organic fluorescence temperature probe application, and in particular relates to a red light material based on excited state proton transfer and a preparation method and application thereof. Background technique [0002] Temperature is one of the most important physical parameters in our daily life. We predict seasonal changes by sensing subtle changes in ambient temperature. We also recognize disease through elevated body temperature. For proper cooking, the temperature of the pan or oven should be precisely controlled. In science, ambient temperature affects all chemical and biochemical reactions. Temperature exists in a wide range of biological activities, and intracellular temperature plays an important role in the cellular functions and biochemical activities of living cells. Abnormal medical phenomena ranging from inflammation to cancer cell growth are often accompanied by elevated body temperat...

Claims

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Application Information

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IPC IPC(8): C07F5/02C09K11/06G01N21/64B82Y30/00B82Y40/00
CPCC07F5/022C09K11/06G01N21/643G01N21/6447B82Y30/00B82Y40/00C09K2211/1007C09K2211/1037C09K2211/1096
Inventor 钱妍侯伟
Owner NANJING UNIV OF POSTS & TELECOMM
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