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532nm excited rhodamine fluorescent dye and preparation method thereof

A fluorescent dye and fluorescent quantum yield technology, applied in the field of rhodamine-based fluorescent dyes and their preparation, can solve the problems of difficult synthesis, complex structure, rare species and the like, and achieve the effects of high reaction yield and simple synthesis steps

Active Publication Date: 2020-06-26
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are few kinds of 532nm small molecule organic fluorescent dyes available, mainly Alexa532, which has a structure of two sulfonic acid groups introduced at the 1 and 8 positions, methyl-modified aza and five-membered ring rhodamine, which has a complex structure and is difficult to synthesize. Difficult to purify, not conducive to the application of actual biological imaging

Method used

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  • 532nm excited rhodamine fluorescent dye and preparation method thereof
  • 532nm excited rhodamine fluorescent dye and preparation method thereof
  • 532nm excited rhodamine fluorescent dye and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Synthesis of target dye Rho-1

[0038] Synthesis of Intermediate 4

[0039]

[0040] Dissolve 1 g of 5-hydroxyquinoline in 30 mL of dry tetrahydrofuran solution, add 1.7 g of nickel perchlorate hexahydrate, and add 1 g of sodium borohydride to the reaction system in small portions while stirring at room temperature. After stirring overnight at room temperature, add 5mL deionized water and stir for 10min, pour into 100mL: 200mL of dichloromethane and water mixture, extract and separate, collect the organic phase, dry with anhydrous sodium sulfate, filter, and remove the solvent from the filtrate under reduced pressure 840 mg of solid was obtained, and the yield was 82%. The hydrogen spectrum data of the NMR spectrum are as follows:

[0041] 1 H NMR(400MHz, CDCl 3 )δ6.83(t,J=8.0Hz,1H), 6.13(d,J=1.5Hz,1H), 6.11(d,J=1.6Hz,1H), 4.62(s,1H), 3.99(s, 1H), 3.26(dd,J=7.1,3.8Hz,2H), 2.65(t,J=6.6Hz,2H), 1.97(dd,J=6.6,5.5,4.4Hz,2H).

[0042] Synthesis of Intermediate 5

[0043]

[0044] W...

Embodiment 2

[0056] Synthesis of target dye Rho-2

[0057] Synthesis of Intermediate 6

[0058]

[0059] Dissolve 1 g of 5-hydroxyquinoline in 30 mL of dry tetrahydrofuran solution, add 1.7 g of nickel perchlorate hexahydrate, and add 1 g of sodium borohydride to the reaction system in small portions while stirring at room temperature. After stirring overnight at room temperature, add 5mL deionized water and stir for 10min, pour into 100mL: 200mL of dichloromethane and water mixture, extract and separate, collect the organic phase, dry with anhydrous sodium sulfate, filter, and remove the solvent from the filtrate under reduced pressure 871 mg of solid was obtained, and the yield was 85%.

[0060] 1 H NMR(400MHz, CDCl 3 )δ6.81(d,J=8.1Hz,1H), 6.12(dd,J=8.1,2.5Hz, 1H), 6.01(d,J=2.4Hz,1H), 3.46(s,1H), 3.29( t,J=5.7,2H),2.70(t,J=6.4Hz, 2H),1.93(td,J=11.4,6.3Hz,2H)

[0061] Synthesis of target dye Rho-2

[0062]

[0063] Weigh 100 mg of 5-hydroxytetrahydroquinoline and 215 mg of Intermediate 5, and ad...

Embodiment 3

[0069] Synthesis of target dye Rho-3

[0070] Synthesis of Intermediate 7

[0071]

[0072] Take 1 g of 4-hydroxytetrahydroquinoline in 15 mL of acetic acid, slowly add 1 g of sodium borohydride in a small amount, and after stirring for 30 minutes, slowly add the acetaldehyde solution. After stirring for 2h at room temperature, the reaction was stopped. Remove most of the acetic acid under reduced pressure, quench with sodium carbonate aqueous solution, adjust the pH to neutral, extract with ethyl acetate, wash and dry, remove most of the solvent, and separate on silica gel column. The eluent is petroleum ether: ethyl acetate =50:1 (volume ratio) to obtain 1.09 g of orange solid, with a yield of 93%. The hydrogen spectrum data of the NMR spectrum are as follows:

[0073] 1 H NMR(400MHz, CDCl 3 )δ6.82(d,J=8.0Hz,1H), 6.24(s,1H), 6.12(d,J=8.0Hz,1H), 3.33(q,J=7.1Hz,2H), 3.28(t, J = 5.7Hz, 2H), 2.70 (t, J = 6.4Hz, 2H), 2.02-1.91 (m, 2H), 1.18 (t, J = 7.1Hz, 3H).

[0074] Synthesis of I...

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Abstract

The invention provides 532nm excited rhodamine fluorescent dye and a preparation method thereof. The structure of the 532nm excited rhodamine fluorescent dye is shown as (1), and the fluorescence quantum yield is higher and reaches 0.85 or above in ethanol through modification with different six-membered ring positions at the nitrogen end. Meanwhile, the raw materials used in the invention are cheap and easily available, the synthesis operation is simple, the requirements on experimental conditions are low, and the dye can be widely applied to the field of bioluminescence imaging.

Description

Technical field [0001] The invention belongs to the field of fluorescent dyes, and specifically relates to a type of rhodamine fluorescent dyes excited at 532 nm and a preparation method thereof. Background technique [0002] With the continuous innovation of life science technology, a variety of new imaging analysis technologies have emerged. Among them, fluorescence imaging technology, as one of the emerging analysis technologies, has the excellent characteristics of non-invasive, real-time observation, high sensitivity and high selectivity, and has been widely used in the fields of biology, medicine, and environmental science. At present, fluorescent substances can be mainly divided into fluorescent proteins, quantum dots and organic small molecule dyes. Compared with the former two, organic small molecule dyes have small size ( <1nm), the absolute advantage of high brightness, and its advantages such as wavelength adjustment and light stability through structural modificat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B57/00C09K11/06G01N21/64
CPCC09B57/00C09K11/06C09K2211/1007C09K2211/1029C09K2211/1088G01N21/6428
Inventor 徐兆超周伟乔庆龙
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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