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A polymer-based universal fluorescent platform for FRET fluorescent probe donors and its applications

A technology of fluorescent probes and polymers, which is applied in the fields of organic chemistry and polymer material chemistry, can solve problems such as complex synthesis processes, and achieve low cost, intuitive detection by naked eyes, and simple and easy synthesis

Active Publication Date: 2022-05-10
DALIAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, in order to combine two fluorophores with different emission wavelengths into one molecule without affecting the ratiometric fluorescence recognition of target molecules, sophisticated molecular design and complex synthesis processes are required.

Method used

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  • A polymer-based universal fluorescent platform for FRET fluorescent probe donors and its applications
  • A polymer-based universal fluorescent platform for FRET fluorescent probe donors and its applications
  • A polymer-based universal fluorescent platform for FRET fluorescent probe donors and its applications

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Experimental program
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Effect test

Embodiment 1

[0025]

[0026] Synthesis of MS-4: In a solution of 6 g of rhodamine hydrazine hydrate (200 mg, 0.46 mmol) in dimethylformamide (about 3 mL), add phenyl isothiocyanate (94 μl, 0.69 μmol) with a molar mass of 1.5 times , gradually raised the temperature to 60°C, heated and stirred for four hours, and after TLC confirmed that the reaction was complete, the reaction solution was extracted with dichloromethane, the organic phase was rotary evaporated under reduced pressure, and the pink target product was obtained by solid column chromatography with a yield of 50%.

Embodiment 2

[0028]

[0029] Synthesis of MS-3: 1 gram of p-hydroxybenzaldehyde, equimolar allyl chloride, and three times the molar amount of potassium carbonate were placed in a 50-ml flask, and 15 ml of acetonitrile was added. The reaction solution was heated to reflux for two hours, cooled and filtered, and the filtrate was spin-dried under reduced pressure to obtain a white solid powder (MS-3 p-allyloxybenzaldehyde), with a yield of 70%. The product was directly used in the next reaction without purification.

[0030] Synthesis of coumarin hydrazine hydrate: coumarin ester (1g, 3.46mmol) was dissolved in 15ml of methanol solution, slowly dripped into 2ml of hydrazine hydrate, the reaction solution was stirred at room temperature for 30 minutes, after TLC confirmed that the reaction was over, the precipitated solid was filtered 0.54 g of yellow solid powder was obtained, with a yield of 56%. The product was directly used in the next reaction without purification.

[0031] Synthesi...

Embodiment 3

[0033]

[0034] Synthesis of MS-2: Mix 5g methyl methacrylate (0.0499mol) and 3.3687g (0.0207mol) MS-3, and add 0.04g initiator azobisisobutyronitrile (0.0002mol) and 20mL dimethyl Formamide was bubbled with nitrogen for 10 min to remove oxygen from the solution. The reaction solution was placed in a constant temperature oil bath, and heated at 70° C. for 24 hours to obtain a transparent polymer. Then the reaction mixture was poured into methanol (200ml), and the polymer was precipitated in methanol, ultrasonically oscillated, filtered, washed with methanol several times to remove the unreacted monomer in the solid part, and the filtered polymer product was placed in a vacuum oven at 30°C Dry for 24 hours to constant weight. Yield: 4.1557 g.

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Abstract

The invention discloses a polymer universal fluorescent platform and its application which can be used as a FRET fluorescent probe donor, and belongs to the technical fields of organic chemistry and polymer material chemistry. In the present invention, methyl methacrylate and 4-allyloxybenzaldehyde are polymerized in a reasonable ratio, and the coumarin fluorophore is further introduced through an efficient Schiff base reaction to prepare the universal polymer blue light platform MS- 1. MS‑1 was prepared step by step from MS‑1 and MS‑2. The polymer universal fluorescence platform prepared by using the coumarin fluorophore in the invention has easy-to-obtain raw materials, simple synthesis and low cost. When combined with mature long-wavelength fluorescent probes, the ratiometric fluorescence detection of target molecules can be realized, and even visual detection by naked eyes can be realized by color.

Description

technical field [0001] The invention belongs to the technical field of organic chemistry and macromolecule material chemistry, and specifically relates to a polymer universal fluorescent platform that can be used as a FRET fluorescent probe donor and its application. Background technique [0002] Since the 21st century, due to the great application potential of optical fiber sensors in industrial analysis, biochemistry, and drug detection, such sensors have been paid close attention to (Adv Optical Mater. 2021, 9, 2001913). Designing such a sensor requires new functional materials with high sensitivity, which is not easy to achieve. Due to its excellent detection performance and easy preparation into polymer fiber materials, fluorescent sensor polymer materials have become the focus of researchers. However, due to the high concentration of fluorescent sensors, fluorescence quenching is easy to occur, which greatly reduces the detection sensitivity. How to maintain the sensi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08F220/14C08F216/14C08F8/32C09K11/06G01N21/64
CPCC08F8/32C08F220/14C09K11/06G01N21/6428C09K2211/145G01N2021/6432G01N2021/6439C08F216/1416
Inventor 张晓琳马思阳孙颂尧马春艳李建军周涛
Owner DALIAN UNIV
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