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Fluorescent dye having phenazine condensed structure and synthesis method of same

A fluorescent dye and fusion technology, applied in the field of fluorescent dyes, can solve the problems of small Stokes shift value and complex synthesis method, and achieve the effects of reducing the interference of self-quenching, simple synthesis steps and high reaction yield.

Active Publication Date: 2018-10-23
HUNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the absorption wavelength and emission wavelength of phenazine fluorescent dyes are generally between the visible light and near-infrared light regions, and the Stokes shift value is small, and the synthesis method is relatively complicated.

Method used

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  • Fluorescent dye having phenazine condensed structure and synthesis method of same
  • Fluorescent dye having phenazine condensed structure and synthesis method of same
  • Fluorescent dye having phenazine condensed structure and synthesis method of same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Example 1 Synthesis of fluorescent dye (DQF-593) with fused structure of type I phenazine

[0049] Dissolve 12 mmol of 4-methoxy-o-phenylenediamine in 30 mL of ethanol, add 12 mmol of cyclohexanedione and react at 60°C for 8 hours. After the reaction is completed, concentrate and pass through a neutral alumina column to obtain 7-methoxy-1, 2,3,4-Tetrahydrophenazine.

[0050] Dissolve 5mmol of 7-methoxy-1,2,3,4-tetrahydrophenazine in 150mmol of anhydrous toluene, slowly add 50mmol of sodium borohydride and 150mmol of acetic acid at 0°C, and then react at 0°C for 1h , after the reaction is completed, warm up to room temperature first, and then heat at 110°C to reflux for 6 hours; after the reaction, slowly pour into water and extract with ethyl acetate, the organic phase is washed, dried, and concentrated to obtain a yellow viscous Intermediate (5,10-diethyl-7-methoxy-1,2,3,4,4a,5,10,10a- octahydrophenazine) (its structure is as shown in (2) in the reaction equation Sho...

Embodiment 2

[0053] Example 2 Synthesis of fluorescent dye (DQF-562) with fused structure of type II phenazine

[0054]

[0055] With 2-carboxy-2', 4'-dihydroxybenzophenone (its structure is as shown in (1) in the reaction equation) 0.2mmol and 5,10-diethyl-7- Dissolve 0.2mmol of methoxy-1,2,3,4,4a,5,10,10a-octahydrophenazine in 5mL of methanesulfonic acid, heat to 90°C for 6h, after the reaction, pour the reaction liquid Put into ice water, then add 6mL of perchloric acid and let it stand until the solid precipitation is complete, then wash the solid, filter with suction, and dry to obtain the crude product. After the crude product is separated by column, the brown product type II phenazine condensed Structure of the fluorescent dye (DQF-562), with high resolution mass spectrometry ( figure 2 ) and NMR analysis. 1 H NMR (400MHz, MeOD) δ8.31(d, J=6.0Hz, 1H), 7.80(2H), 7.38(d, J=7.6Hz, 1H), 7.18(d, J=8.1Hz, 1H), 7.12(s,1H),7.05(s,1H),6.93(d,J=7.5Hz,1H),6.09(d,J=7.6Hz,1H),3.89(s,1H),3...

Embodiment 3

[0056] Example 3 Synthesis of fluorescent dye (DQF-683) with fused structure of type III phenazine

[0057] Dissolve 12mmol of o-phenylenediamine in 30mL of ethanol, add 14mmol of cyclohexanedione, then react at 60°C for 8h, the mixture is concentrated and passed through a neutral alumina column to obtain 1,2,3,4-tetrahydrophenazine.

[0058] Dissolve 5 mmol of 1,2,3,4-tetrahydrophenazine in 30 mL of anhydrous toluene, slowly add 50 mmol of sodium borohydride and 30 mL of acetic acid at 0°C, and then react at 0°C for 1 hour. After the reaction is completed, first The temperature was raised to room temperature, and then heated to reflux at 110°C for 7 hours; after the reaction, it was slowly poured into water, extracted with ethyl acetate, and the organic phase was washed, dried, and concentrated to obtain a yellow viscous intermediate 5,10- Diethyl-1,2,3,4,4a,5,10,10a-octahydrophenazine (its structure is shown in (2) in the reaction equation).

[0059]

[0060] 4-diethylam...

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Abstract

The invention discloses a fluorescent dye having phenazine condensed structure, of which the structural formula is represented as one of the formulas (I) to (IV). The fluorescent dye having phenazinecondensed structure is prepared through steps of: reactions of cyclohexanedione condensation, sodium borohydride reduction, Vilsmeier formylation and the like are carried out to obtain an intermediatecompound; and then reactions with 4-subsituent amino-2-nitrosophenol, benzophenone acid, trans-4-subsituent amino-salicylaldehyde and the like compounds are carried out. Compared with classical fluorescent dyes (e.g. rhodamine, oxazine, squaric acid, anthocyanin dyes), the fluorescent dye in the invention has high photo-stability, is near-infrared in fluorescence emission wavelength of 635-829 nm, and has large Stokes shift capable of reaching 122 nm and high fluorescence quantum yield capable of reaching 0.43. The fluorescent dye can be applied to fields such as luminescent materials, bio-fluorescence probes, multicolor fluorescence imaging, etc.

Description

technical field [0001] The invention belongs to the technical field of fluorescent dyes, and in particular relates to a fluorescent dye with a phenazine condensed structure and a synthesis method thereof. Background technique [0002] Organic small molecule fluorophores are widely used in biomolecular labeling, enzyme analysis, environmental analysis, cell staining, and clinical laboratory diagnosis. They are indispensable and important tools in chemistry, biology, physics, environmental science, and medical research. Therefore, the development of various functional fluorescent dye molecules with practical value has become a research hotspot that has attracted much attention. In particular, fluorescent dyes with near-infrared emission wavelengths (Em>650nm) are widely used in biological tissues due to their deep tissue penetration ability to biological tissue samples, low light damage, and low biological background fluorescence interference. imaging field. Molecular flu...

Claims

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Application Information

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IPC IPC(8): C07D491/052C07D491/22C07D498/04C07F7/08C09B57/00C09K11/06G01N21/64
CPCC07D491/052C07D491/22C07D498/04C07F7/0816C07F7/0827C09B57/00C09K11/06C09K2211/1029C09K2211/1033C09K2211/1044C09K2211/1088C09K2211/1096G01N21/6428G01N2021/6432
Inventor 袁林任天兵张晓兵张维
Owner HUNAN UNIV
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