WO2018099382A1 - Colorant fluorescent excité par la lumière rouge, son procédé de préparation et ses applications - Google Patents

Colorant fluorescent excité par la lumière rouge, son procédé de préparation et ses applications Download PDF

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WO2018099382A1
WO2018099382A1 PCT/CN2017/113465 CN2017113465W WO2018099382A1 WO 2018099382 A1 WO2018099382 A1 WO 2018099382A1 CN 2017113465 W CN2017113465 W CN 2017113465W WO 2018099382 A1 WO2018099382 A1 WO 2018099382A1
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fluorescent dye
red light
add
preparation
reaction
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PCT/CN2017/113465
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Chinese (zh)
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车团结
徐进章
赵芳
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苏州百源基因技术有限公司
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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B57/00—Other synthetic dyes of known constitution
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
    • G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
    • G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
    • G01N21/64—Fluorescence; Phosphorescence
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
    • G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
    • G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
    • G01N21/64—Fluorescence; Phosphorescence
    • G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
    • G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
    • G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
    • G01N21/64—Fluorescence; Phosphorescence
    • G01N21/6486—Measuring fluorescence of biological material, e.g. DNA, RNA, cells
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/655—Aromatic compounds comprising a hetero atom comprising only sulfur as heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1022—Heterocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • C09K2211/1055—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with other heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]

Definitions

  • the invention relates to the field of optical functional materials, in particular to a red light excitation fluorescent dye and a preparation method and application thereof.
  • fluorescent dyes Dyes that strongly absorb and radiate fluorescence in the visible range are called fluorescent dyes. Fluorescent dyes emit visible fluorescence after absorption of red light by a substance molecule and absorb visible light with a longer wavelength after absorption of shorter wavelength visible light. Each molecule has a series of strict discrete energy levels. At room temperature, most of the material molecules are in the "ground state”. When these materials absorb light energy under the illumination of light, they enter a new state called “excited state”. The molecular weight of the excited state is unstable, and it can emit light to return to the ground state in a very short time of 10 -9 to 10 -7 seconds, and the process fluoresces. Since the 20th century, fluorescent dyes have been widely used in various industries such as textiles, plastic dyeing, and printing pigments.
  • fluorescent dyes have been widely used to label, detect, and/or quantify components in samples, and various methods for such detection and/or quantification include fluorescence microscopy, fluorescent immunoassays, and flow of cells. Cell count analysis, as well as a variety of other applications.
  • Organic fluorescent compounds having an electron donor group- ⁇ bridge-electron acceptor group structure Specific optical properties are exhibited.
  • the Stokes' displacement is large, and the luminescent properties vary greatly depending on the polarity and viscosity of the solvent, and the two-photon absorption ability is strong, which is receiving more and more attention.
  • They have great application value in many aspects, for example, they can be used to construct photoelectric molecular switches, light-emitting diodes, field effect transistors, information transmission and storage devices.
  • these molecules are highly sensitive to the environment and can be used as fluorescent probe materials (WO2007013601-A1) in the fields of biomarkers, immunoassays and chemical sensing (DE102004059156-A1).
  • red light-excited fluorescent dye that can ensure the stability of the spectral analysis signal, has a high molar absorptivity, has a high fluorescence quantum yield, and has certain chemical activity and easy structure modification. Therefore, its further application in the fields of biology, environment and the like is limited.
  • the invention designs and synthesizes a novel red light-excited fluorescent dye with novel structure, simple preparation method and excellent performance.
  • the technical problem to be solved by the present invention is to overcome the difficulty in synthesizing the red light-excited fluorescent dye in the prior art.
  • red light-excited fluorescent dye having a structure as shown in formula (I):
  • R 1 , R 2 and R 3 are one selected from the group consisting of hydrogen, a C 1 -C 10 hydrocarbon group, a cyano group, an aryl group or a heterocyclic ring.
  • R 1 , R 2 , and R 3 are selected from the group consisting of hydrogen, methyl, ethyl, cyano, phenyl, 2-thienyl, and 3-thienyl.
  • a method of preparing the red light-excited fluorescent dye comprising the steps of:
  • the present invention further provides the red light-excited fluorescent dye in constructing a photoelectric molecular switch, a light emitting diode, a field effect transistor, an information transmission and storage device, and also can be used as a fluorescent probe for biomarking and immunity. Analysis and areas such as chemical sensing.
  • the red light-excited fluorescent dye application method is an application of dissolving in any ratio of dimethylformamide, ethanol, hydroxyethylpiperazineethanesulfonic acid in any ratio.
  • a red light-excited fluorescent dye provided by an embodiment of the present invention, which contains a benzene ring or a hetero ring and has a conjugated double bond, and is excited when the non-bonded electron of the O or N atom is in an excited state.
  • the ⁇ * bond is characterized by expanding the large ⁇ bond of the organic fluorescent molecule, expanding the conjugated system of the entire organic fluorescent molecule, and enhancing the fluorescence of the organic molecule.
  • the fluorescent dye has simple synthesis process, high selectivity, and is not easy to be polymerized, and has a large molar extinction coefficient, high sensitivity, and fluorescence by introducing an electron withdrawing group.
  • High quantum yield and good light stability when used for the detection of substances in living organisms, can greatly reduce the self-absorption and autofluorescence interference of substances in the living body, improve the sensitivity and selectivity of detection, and reduce Damage to life.
  • Example 1 is an excitation and emission spectrum of a red light-excited fluorescent dye in ethanol of Example 1-4 of the present invention
  • the basic chemical raw materials such as reagents used in the embodiments of the present invention can be purchased in the domestic chemical product market, or can be customized in the relevant intermediate preparation factory.
  • the preparation method is as follows:
  • the red light-excited fluorescent dye (II) of the present invention is detected and characterized as follows:
  • the preparation method is as follows:
  • the red light-excited fluorescent dye (III) of the present invention is detected and characterized as follows:
  • the preparation method is as follows:
  • the red light-excited fluorescent dye (IV) of the present invention is detected and characterized as follows:
  • the preparation method is as follows:
  • the red light-excited fluorescent dye (V) of the present invention is detected and characterized as follows:
  • the fluorescence spectrum, the molar extinction coefficient and the fluorescence quantum yield are determined, and the specific determination methods of each parameter are as follows:
  • the compound to be determined was accurately weighed and prepared into a solution having a concentration of 1.0 ⁇ 10 -5 mol/L, and the absorption spectrum thereof was measured, as shown in Fig. 1.
  • the fluorescence spectrum was measured using the maximum absorption wavelength in the measured red spectrum as the excitation wavelength of the fluorescence spectrum.
  • the test compound was weighed, and an ethanol:water (50:50, v/v) solution having a concentration of 1.0 ⁇ 10 -6 mol/L was prepared, and its emission spectrum was measured, as shown in FIG.
  • A represents the absorption intensity
  • ⁇ is the molar absorption coefficient
  • c is the concentration of the compound
  • l is the thickness of the quartz cell for detection.
  • the fluorescence quantum yield of the red-excited fluorescent dye was measured at 20 ° C.
  • the quinine sulfate (0.1 M H 2 SO 4 solvent with a quantum yield of 0.56) was used as a reference to measure the red fluorescent excitation dye and
  • the fluorescence quantum yield is calculated by the fluorescence integrated intensity obtained from the dilute solution of the reference material under the same excitation conditions and the ultraviolet absorption value at the excitation wavelength.
  • the product was dissolved in absolute ethanol.
  • ⁇ is the quantum yield of the analyte
  • subscript R represents the reference.
  • I is the fluorescence integrated intensity
  • A is the ultraviolet absorption value.
  • ⁇ is the solvent refractive index.
  • the absorbances A and A R are less than 0.1.
  • the red light-excited fluorescent dye (IV) described in Example 3 has the largest absorption wavelength, and corresponds to the maximum emission wavelength of 747 nm, the maximum molar absorption coefficient of 8.9, and the maximum fluorescence quantum yield of 88.67%. , which further indicates that the compounds have advantages in constructing photoelectric molecular switches, light-emitting diodes, field effect transistors, information transmission and storage devices, and It is used as a fluorescent probe in the fields of biomarkers, immunoassays, and chemical sensing.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Immunology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Analytical Chemistry (AREA)
  • General Physics & Mathematics (AREA)
  • Pathology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Optics & Photonics (AREA)
  • Biomedical Technology (AREA)
  • Molecular Biology (AREA)
  • Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
  • Luminescent Compositions (AREA)
  • Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)

Abstract

La présente invention concerne le domaine des matériaux à fonction optique et, plus particulièrement, un colorant fluorescent excité par la lumière rouge ayant une structure représentée par la formule (I). Le colorant fluorescent excité par la lumière rouge selon la présente invention présente un spectre d'excitation très large, une bonne stabilité à la lumière et une stabilité élevée dans la détection de traces, peut être utilisé dans différents domaines d'application tels que l'imagerie cellulaire, les sondes fluorescentes, les colorants à laser et les capteurs de fluorescence et présente une bonne aptitude à la mise en œuvre. Le procédé de préparation selon la présente invention présente de faibles coûts de matière première, ne produit pas de pollution, nécessite des technologies simples et a un rendement élevé ; le colorant fluorescent préparé présente une nouvelle structure et de bonnes performances et est approprié pour être largement utilisé dans les domaines tels que la biologie et l'environnement.
PCT/CN2017/113465 2016-11-30 2017-11-29 Colorant fluorescent excité par la lumière rouge, son procédé de préparation et ses applications WO2018099382A1 (fr)

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CN201611085796.0 2016-11-30

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Cited By (4)

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Publication number Priority date Publication date Assignee Title
CN110563609A (zh) * 2019-09-26 2019-12-13 河南省农业科学院农业质量标准与检测技术研究所 一种检测***根的近红外荧光探针的制备方法及应用
CN113185550A (zh) * 2021-05-13 2021-07-30 井冈山大学 一种用于Pickering乳液凝胶化程度检测的荧光传感器及其制备和应用
CN114907836A (zh) * 2022-05-07 2022-08-16 西北工业大学 一种多级光响应型荧光液晶基元及其聚合物及制备方法
CN115215849A (zh) * 2022-07-15 2022-10-21 浙江工业大学 具有大斯托克斯位移的红色双光子荧光化合物及其合成与应用

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* Cited by examiner, † Cited by third party
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CN108913157A (zh) * 2018-06-21 2018-11-30 张楠楠 一种高荧光有机硼液晶新材料的制备方法
CN110108682B (zh) * 2019-05-08 2021-09-24 济南大学 几种非典型红光含硅染料的应用

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110563609A (zh) * 2019-09-26 2019-12-13 河南省农业科学院农业质量标准与检测技术研究所 一种检测***根的近红外荧光探针的制备方法及应用
CN113185550A (zh) * 2021-05-13 2021-07-30 井冈山大学 一种用于Pickering乳液凝胶化程度检测的荧光传感器及其制备和应用
CN113185550B (zh) * 2021-05-13 2022-04-19 井冈山大学 一种用于Pickering乳液凝胶化程度检测的荧光传感器及其制备和应用
CN114907836A (zh) * 2022-05-07 2022-08-16 西北工业大学 一种多级光响应型荧光液晶基元及其聚合物及制备方法
CN114907836B (zh) * 2022-05-07 2023-10-27 西北工业大学 一种多级光响应型荧光液晶基元及其聚合物及制备方法
CN115215849A (zh) * 2022-07-15 2022-10-21 浙江工业大学 具有大斯托克斯位移的红色双光子荧光化合物及其合成与应用
CN115215849B (zh) * 2022-07-15 2024-01-12 浙江工业大学 具有大斯托克斯位移的红色双光子荧光化合物及其合成与应用

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