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Water-soluble PnO2-PODIPY/PnO2-azaPODIPY fluorescent dye and preparation method thereof

A fluorescent dye, water-soluble technology, used in nitro/nitroso dyes, azo dyes, organic dyes, etc.

Inactive Publication Date: 2015-02-18
SHENYANG INSTITUTE OF CHEMICAL TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, methylenedipyrrole / azamethylenedipyrrole as a ligand to complex PnO2 (Pn = P, As, Sb, Bi) dyes has never been reported and investigated.

Method used

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  • Water-soluble PnO2-PODIPY/PnO2-azaPODIPY fluorescent dye and preparation method thereof
  • Water-soluble PnO2-PODIPY/PnO2-azaPODIPY fluorescent dye and preparation method thereof
  • Water-soluble PnO2-PODIPY/PnO2-azaPODIPY fluorescent dye and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0075] Preparation of Fluorescent Dye I-1

[0076]

[0077] (1) Synthesis of intermediate compound III-1.

[0078] Under argon protection, p-nitrophenylaldehyde (300 mg, 0.19 mmol) and 2,4-dimethylpyrrole (0.51 ml, 0.49 mmol) were dissolved in dichloromethane (20 ml), and a drop of trifluoro Acetic acid, stirred at room temperature, reacted for 12 h. The completion of the reaction was detected by TLC, DDQ (900 mg) was added and stirred for 30 minutes. The reaction solution was quenched with ice. It was extracted with dichloromethane, distilled under reduced pressure, and the residue was purified with a silica gel column. The developing solvent was dichloromethane / n-hexane to obtain a yellow solid III-1 (183.2 mg, 30 %).

[0079] (2) Synthesis of PO2-PODIPY dye I-1.

[0080] Under an open system, the obtained solid III-1 (64.2 mg) was dissolved in dichloromethane (20 ml), then triethylamine (0.7 ml) was added, and reacted for 10 minutes. Then, phosphorus oxychloride (1...

Embodiment 2

[0082] Preparation of fluorescent dye IIa-1

[0083]

[0084] (1) Synthesis of intermediate compound IVa-1

[0085] In an open system, add 2,4-diphenylpyrrole (43.8 mg, 0.2 mmol), glacial acetic acid (1 ml), acetic anhydride (0.4 ml), add sodium nitrite (6.9 mg, 0.1 mmol) under ice cooling, React at room temperature for 0.5 h, transfer to 80 °C for 0.5 h, and the reaction ends. The reaction was quenched by adding ice water, a solid would precipitate out, and the solid was filtered out. The filter cake was dissolved in dichloromethane, passed through the column with dichloromethane as the eluent and alumina as the stationary phase, and the solvent was spin-dried to obtain blue-purple solid IVa-1 (35.9 mg, 80%). 1 H NMR (400 MHz, CDCl 3 ) 8.04-8.08 (m, 4H), 7.94-7.97 (m, 4H), 7.33-7.57 (m, 12H), 7.21 (s, 2H) (NH not observed). 13 C NMR (CDCl3) 155.1, 149.6, 142.7, 133.7, 132.2, 130.1, 129.2, 129.1, 128.3, 128.0, 126.6, 114.9.

[0086] (2) Synthesis of PO2-azaPODIPY d...

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Abstract

The invention relates to a dye and a preparation method thereof. The fluorescent dye is a series of novel dye which takes PnO2-PODIPY / PnO2-azaPODIPY developed from dipyrrin / aza-dipyrromethene complexing PnO2 (Pn-P, As, Sb, Bi) as a parent nucleus, and the general formula of the fluorescent dye is as shown in I / II. The fluorescent dye disclosed by the invention has the advantages of spectral property and the like of the classic traditional dye BODIPY / azaBODIPY. Although a central atom Pn is a sexadentate, the fluorescent dye is stable without being decomposed in air and a water solution. The compound has the outstanding characteristics of excellent water solubility and certain cell membrane permeability and can be used for biological dyeing. The novel dye disclosed by the invention has a novel spectral characteristic and can be applied to the aspect of fluorescence imaging.

Description

technical field [0001] The present invention relates to a kind of dye and preparation method thereof, especially relate to a kind of water-soluble PnO2 -PODIPY / PnO2 - azaPODIPY fluorescent dye and preparation method thereof. Background technique [0002] Non-invasive, real-time imaging of physiological and pathological processes in life or in vivo at the molecular and cellular levels is of great significance for accurate diagnosis of diseases before morphological changes occur in the body. Fluorescent dyes, as functional dyes, have been widely used in this field and have attracted much attention. [0003] Among many dyes, BF2-dipyrrolemethene (BODIPY for short) fluorescent dyes have many advantages such as high fluorescence quantum yield, good photostability, absorption and emission wavelengths in the visible light region, and easy regulation, and are widely used. Research, its molecules are easy to modify. [0004] BF2-azadipyrrolemethene (azaBODIPY) dyes are a new t...

Claims

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Application Information

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IPC IPC(8): C09B51/00C09B57/00C09K11/06G01N21/64
Inventor 姜新东赵九丽肖林久习东梅于海峰于秀兰姚晓东周凡
Owner SHENYANG INSTITUTE OF CHEMICAL TECHNOLOGY
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