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A class of near-infrared fluorescent dyes based on rhodamine and its preparation method and application

A fluorescent dye and near-infrared technology, applied in luminescent materials, fluorescence/phosphorescence, coumarin dyes, etc., can solve the problems of large Stokes shift, application limitations, short absorption and emission wavelengths, etc.

Active Publication Date: 2017-03-08
TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Traditional coumarin fluorescent dyes have many advantages such as large Stokes shift, good photostability, relatively small molecular volume, and good oil solubility. However, the absorption and emission wavelengths are too short, which greatly limits its application.

Method used

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  • A class of near-infrared fluorescent dyes based on rhodamine and its preparation method and application
  • A class of near-infrared fluorescent dyes based on rhodamine and its preparation method and application
  • A class of near-infrared fluorescent dyes based on rhodamine and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0140]

[0141] 7-Dimethylamino-4-hydroxycoumarin II-1 was prepared from 3-N,N-dimethylaminophenol according to literature (Chem. Commun., 2006, 3886-3888), with a total yield of 80%.

[0142] Mix 0.233g (0.001mol) of compound II-1 and 0.313g (0.001mol) of compound III-1 in 10ml of tetrachloroethane, add 1.42g (0.01mol) of phosphorus pentoxide in batches, and reflux for 5 hours , add 20 ml of water after cooling, extract three times with 20 ml of chloroform, after the chloroform phase is dried, evaporate the solvent under reduced pressure, dissolve the resulting product in 10 ml of ethanol, add 2 ml of perchloric acid (70%), slowly drop Distilled water, precipitated solid, filtered, vacuum dried, and purified by column chromatography to obtain 0.22 g of compound I-1 with a yield of 36.1%. ESI MS: m / z, 511.2. lambda ab. max / nm=595nm,λ em max / nm=648nm,Ф f =0.32.

[0143] Dissolve 0.194g (0.33mmol) of compound I-1, 0.038g (0.33mmol) of N-hydroxysuccinimide, and dicycl...

Embodiment 2

[0145]

[0146] Compound II-2 was prepared from 8-hydroxyjuloridine according to the literature (Chem.Commun., 2006, 3886–3888), with a total yield of 75%; Compound III-2 was prepared according to the literature (J.Arden-Jacob, Ph.D .Thesis, Verlag Shaker, Aachen, 1993.) Prepared from 8-hydroxy-juloridine and phthalic anhydride with a yield of 20%.

[0147] Mix 0.257g (0.001mol) of compound II-2 and 0.337g (0.001mol) of compound III-2 in 10ml of tetrachloroethane, add 0.71g (0.005mol) of phosphorus pentoxide in batches, and reflux for 8 hours , add 20 ml of water after cooling, extract three times with 20 ml of chloroform, after the chloroform phase is dried, evaporate the solvent under reduced pressure, dissolve the resulting product in 10 ml of ethanol, add 2 ml of perchloric acid (70%), slowly drop Distilled water, precipitated a solid, filtered, dried in vacuo, and purified by column chromatography to obtain 0.25 g of compound I-3 with a yield of 36.1%. ESI MS: m / z, 55...

Embodiment 3

[0150]

[0151] Compound II-3 was prepared from 7-hydroxy-1-methyl-1,2,3,4-tetrahydroquinoline according to literature (Chem.Commun., 2006, 3886-3888), with a total yield of 85%; Compound III -3 According to the literature (J.Arden-Jacob, Ph.D.Thesis, VerlagShaker, Aachen, 1993.) from 7-hydroxy-1-methyl-1,2,3,4-tetrahydroquinoline and phthalate Preparation of formic anhydride with a yield of 25%.

[0152] Mix 0.231g (0.001mol) of compound II-3 and 0.311g (0.001mol) of compound III-3 in 10ml of tetrachloroethane, add 1.42g (0.01mol) of phosphorus pentoxide in batches, and reflux for 2 hours , add 20 ml of water after cooling, extract three times with 20 ml of chloroform, after the chloroform phase is dried, evaporate the solvent under reduced pressure, dissolve the resulting product in 10 ml of ethanol, add 2 ml of perchloric acid (70%), slowly drop Distilled water, precipitated solid, filtered, vacuum dried, and purified by column chromatography to obtain 0.21 g of compoun...

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PUM

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Abstract

The invention discloses a rhodamine based near-infrared fluorescent dye having the following structural formula (I), wherein Y is O or S; Z is NR6R7 or OR8; R1, R2, R6, R7 and R8 respectively independently are hydrogen, alkyl, ether group, substituted alkyl, acyl, or aryl; R3, R4, R5, R9, R10 and R11 independently are hydrogen, low alkyl, lower alkoxy, cyanogroup or halogen; R12, R13, R14, R15 and R16 independently are hydrogen, low alkyl, lower alkoxy, halogen, formyl, formate group, sulfonic group, sulfonate grop, sulfonyl chloride group, formic acid ester group, formyl halide group, formamide group, hydroxyl, amino, cyanogroup, isocyanate group, isothiocyanate group or amine group; X is a negative ion. The invention also discloses a preparation method of the rhodamine based near-infrared fluorescent dye. The rhodamine based near-infrared fluorescent dye has good biocompatibility and photostability, low toxicity, long fluorescence emission and high fluorescence quantum yield, and can be used in covalent fluorescent labeling of biological macromolecules and fluorescent probe fluorophore.

Description

technical field [0001] The invention relates to a class of near-infrared fluorescent dyes and their preparation methods and applications, in particular to a class of rhodamine-based near-infrared fluorescent dyes and their preparation methods and applications. Background technique [0002] In recent years, it is of great significance to the development of fields such as revealing the mysteries of life, clinical diagnosis and drug screening, and fluorescence imaging is becoming an important technology in biological research. This is mainly due to the emergence of more and more fluorescent probes, including small molecule fluorescent probes, nano-quantum dots, and fluorescent proteins. Fluorescent protein tracer technology has been widely used in biomedical research. However, fluorescent proteins have problems such as large molecular weight, large steric hindrance, and interference caused by protein-protein interactions. The safety of nano-quantum dots has always been uncertai...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09B57/02C09K11/06G01N21/64
Inventor 刘卫敏汪鹏飞陈建宏
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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