CN110283586A - A kind of near infrared fluorescent dye and preparation method thereof - Google Patents
A kind of near infrared fluorescent dye and preparation method thereof Download PDFInfo
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- CN110283586A CN110283586A CN201910624037.4A CN201910624037A CN110283586A CN 110283586 A CN110283586 A CN 110283586A CN 201910624037 A CN201910624037 A CN 201910624037A CN 110283586 A CN110283586 A CN 110283586A
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- near infrared
- fluorescent dye
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
- C07D265/38—[b, e]-condensed with two six-membered rings
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- 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
- C09B19/00—Oxazine dyes
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- 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
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- 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
- C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
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- Organic Chemistry (AREA)
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- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Abstract
The present invention relates to a kind of near infrared fluorescent dyes and preparation method thereof, pass through nitration reaction, hydrogen reduction method and air oxidation process, a kind of novel near infrared fluorescent dye of phenoxazine zionoes is rapidly and efficiently synthesized, preparation method is environmentally protective, and industrialized production difficulty is low, profit is high；Near infrared fluorescent dye of the invention has that near infrared emission, quantum yield are high, and yield is up to 27.55%, and dyeability is excellent, favorable solubility and is synthetically prepared simple feature；It can be widely applied to bio-imaging technology, fluorescence probe kit, antibody and protein labeling, cancer target label and drug modification exploitation aspect, it has a good application prospect, it is also widely applied to the industries such as anti-counterfeit printing, pesticide, dyestuff, building and food inspection, application value with higher simultaneously.
Description
Technical field
The invention belongs to dyestuff processing technique fields, and in particular to a kind of phenoxazine zionoes near infrared fluorescent dye and its system
Preparation Method.
Background technique
Near-infrared fluorescent has the characteristics that penetration into tissue is strong, background fluorescence interference is low, biological sample light injury is small, causes
People more and more pay close attention to.But in practical applications, some near infrared fluorescent dyes there are itself easily polymerization, dissolubility compared with
Difference is synthetically prepared the difficult defects such as low with quantum yield.
Small organic molecule fluorescent dye had been widely used in photocatalysis, photoelectric material, analysis detection, biology in recent years
Molecular labeling, clinical diagnosis etc. are works indispensable in chemistry, material science, environmental science and biomedical research
Tool.In current commercialized near infrared fluorescent dye, there are still the defects of some aspects, as stability is poor, is easy to assemble, dissolution
Property is poor, is difficult to modify, and greatly limits application of such dyestuff in all trades and professions.
Summary of the invention
Of the existing technology in order to solve the problems, such as, the present invention provides a kind of near infrared fluorescent dye and its users
Method, near infrared fluorescent dye of the invention are a kind of novel near infrared fluorescent dyes, have near infrared emission, quantum yield
Height, dyeability is excellent, favorable solubility and is synthetically prepared simple feature.
The object of the present invention is to provide a kind of near infrared fluorescent dyes.
Another object of the present invention is to provide the preparation method of above-mentioned near infrared fluorescent dye.
The near infrared fluorescent dye of specific embodiment according to the present invention, the structural formula of the near infrared fluorescent dye is such as
(a) shown in:
The near infrared fluorescent dye of specific embodiment according to the present invention, the reaction equation of the method such as (b) institute
Show:
The preparation method of the near infrared fluorescent dye the following steps are included:
(1) to dense H2SO4Middle addition N, N- diethyl -3- hydroxyanilines, stirring make dissolution of raw material, and NaNO is added3, continue
Stirring pours into reaction solution in ice water to after the reaction was completed, and a large amount of yellow-brown solids are precipitated, and decompression filters, filter cake deionization
Water washing, vacuum drying obtain filter cake compound；
(2) the filter cake compound obtained by step (1) is dissolved in ethyl alcohol, is reacted in atmosphere of hydrogen, to reaction solution face
Hydrogen is removed when color becomes colorless, and is admitted air into reaction flask, solution colour becomes blue black color, continues to be stirred to react 9-11h,
Stop reaction；Then vacuum distillation removes solvent and obtains crude product, by the crude product through chromatography post separation, obtains target chemical combination
Object.
The near infrared fluorescent dye of specific embodiment according to the present invention, wherein in step (1), the addition
NaNO3, the time for continuing stirring is 6-8h.
The near infrared fluorescent dye of specific embodiment according to the present invention, wherein under condition of ice bath, to dense H2SO4In
N, N- diethyl -3- hydroxyanilines is added, stirring makes dissolution of raw material, keeps ice bath that NaNO is added3, room temperature continue stir 6-8h,
After the reaction was completed, reaction solution is poured into ice water, is precipitated a large amount of yellow-brown solids, decompression filters, filter cake with deionized water repeatedly
Washing, at least three times, vacuum drying obtain filter cake compound.Sodium nitrate is solid, according to the number of the amount of addition, need to slowly be divided
It criticizes and is added, addition is too fast to will lead to reaction system local heating unevenness, tobacco of emerging.Sodium nitrate is added under condition of ice bath, it is to be added
Complete sodium nitrate, reaction system the reaction was continued at normal temperature 6-8h.Due to there is a large amount of concentrated sulfuric acids in reaction system, reaction solution needs slow
It pours into ice water, prevents liquid splash.
The near infrared fluorescent dye of specific embodiment according to the present invention, wherein in step (1), the N, N- diethyl
Base -3- hydroxyanilines and the NaNO3Molar ratio be 29-31:33.
The near infrared fluorescent dye of specific embodiment according to the present invention, wherein the N, N- diethyl -3- hydroxyl
Aniline and the NaNO3Molar ratio be 10:11.
The near infrared fluorescent dye of specific embodiment according to the present invention, wherein every dense H of 40mL2SO4Middle addition
The NaNO of the N of 30mmol, N- diethyl -3- hydroxyanilines and 33mmol3。
The near infrared fluorescent dye of specific embodiment according to the present invention, wherein dense to 40mL under condition of ice bath
H2SO4The middle N that 30mmol is added, N- diethyl -3- hydroxyanilines, stirring make dissolution of raw material, and ice bath is kept to be added 33mmol's
NaNO3, room temperature, which continues to stir 7h, until after the reaction was completed, reaction solution is poured slowly into 200mL ice water is precipitated a large amount of brown colors
Solid, decompression filter, and filter cake is washed repeatedly with deionized water, and at least three times, vacuum drying obtains filter cake compound.
The near infrared fluorescent dye of specific embodiment according to the present invention, wherein in step (2), by the filter cake
It closes object to be dissolved in ethyl alcohol, palladium carbon is added as catalyst, reacts in atmosphere of hydrogen, becomes colorless to reaction solution color at room temperature
When remove hydrogen, admit air into reaction flask, solution colour becomes blue black color, continues stirring at normal temperature and reacts 10h, stops anti-
It answers；Then it filters out palladium carbon and is evaporated under reduced pressure removing solvent and obtain crude product, by the crude product through chromatography post separation, obtain target
Compound.
The near infrared fluorescent dye of specific embodiment according to the present invention, further, the crude product is through silica gel color
Post separation is composed, eluant, eluent used is methylene chloride.
Compared with prior art, the invention has the following beneficial effects:
(1) near infrared fluorescent dye of the invention is a kind of novel near infrared fluorescent dye, has near infrared emission, amount
Sub- yield is high, and yield is up to 27.55%, and dyeability is excellent, favorable solubility and is synthetically prepared simple feature.
(2) present invention rapidly and efficiently synthesizes a kind of phenoxazine ketone by nitration reaction, hydrogen reduction method and air oxidation process
The novel near infrared fluorescent dye of class, preparation method is environmentally protective, and industrialized production difficulty is low, profit is high；
(3) near infrared fluorescent dye that is obtained by directional transformation of the present invention can be widely applied to bio-imaging technology, glimmering
Light probe kit, antibody and protein labeling, cancer target label and drug modification exploitation aspect, before there is application well
Scape, while the industries such as anti-counterfeit printing, pesticide, dyestuff, building and food inspection are also widely applied to, it is with higher to apply valence
Value.
Detailed description of the invention
Fig. 1 is the nuclear magnetic resonance spectroscopy of near infrared fluorescent dye of the invention；
Fig. 2 is the carbon-13 nmr spectra figure of near infrared fluorescent dye of the invention；
Fig. 3 is the mass spectrogram of near infrared fluorescent dye of the invention；
Fig. 4 is the fluorescence spectrum of near infrared fluorescent dye of the invention in different solvents.
Specific embodiment
To make the object, technical solutions and advantages of the present invention clearer, technical solution of the present invention will be carried out below
Detailed description.Obviously, described embodiments are only a part of the embodiments of the present invention, instead of all the embodiments.Base
Embodiment in the present invention, those of ordinary skill in the art are obtained all without making creative work
Other embodiment belongs to the range that the present invention is protected.
Various raw materials used in the present invention are ordinary commercial products, or by well known to a person skilled in the art
Method disclosed in method or the prior art obtains.
Embodiment 1
A kind of near infrared fluorescent dye is present embodiments provided, structural formula is such as shown in (a):
The synthetic route of the near infrared fluorescent dye is such as shown in (b):
The preparation method of the near infrared fluorescent dye the following steps are included:
(1) to dense H2SO4Middle addition N, N- diethyl -3- hydroxyanilines, stirring make dissolution of raw material, and NaNO is added3, continue
Stirring pours into reaction solution in ice water to after the reaction was completed, and a large amount of yellow-brown solids are precipitated, and decompression filters, filter cake deionization
Water washing, vacuum drying obtain filter cake compound；
(2) the filter cake compound obtained by step (1) is dissolved in ethyl alcohol, is reacted in atmosphere of hydrogen, to reaction solution face
Hydrogen is removed when color becomes colorless, and is admitted air into reaction flask, solution colour becomes blue black color, continues to be stirred to react 9-11h,
Stop reaction；Then vacuum distillation removes solvent and obtains crude product, by the crude product through chromatography post separation, obtains target chemical combination
Object.
Embodiment 2
A kind of near infrared fluorescent dye is present embodiments provided, structural formula is such as shown in (a):
The synthetic route of the near infrared fluorescent dye is such as shown in (b):
The preparation method of the near infrared fluorescent dye the following steps are included:
(1) under condition of ice bath, to the dense H of 40mL2SO4The middle N that 30mmol is added, N- diethyl -3- hydroxyanilines, stirring
Make dissolution of raw material, keeps ice bath that the NaNO of 33mmol is added3, room temperature continues to stir 7h, until after the reaction was completed, reaction solution is slow
It pours into 200mL ice water, a large amount of yellow-brown solids is precipitated, decompression filters, and filter cake is washed repeatedly with deionized water, at least three times,
Vacuum drying obtains filter cake compound；
(2) the filter cake compound is dissolved in ethyl alcohol, palladium carbon is added as catalyst, at room temperature in atmosphere of hydrogen instead
It answers, removes hydrogen when reaction solution color becomes colorless, admit air into reaction flask, solution colour becomes blue black color, continues
Stirring at normal temperature reacts 10h, stops reaction；Then it filters out palladium carbon and is evaporated under reduced pressure removing solvent and obtain crude product, by the thick production
Object is methylene chloride through silica gel chromatograph post separation, eluant, eluent used, obtains target compound.
Embodiment 3
A kind of near infrared fluorescent dye is present embodiments provided, structural formula is such as shown in (a):
The synthetic route of the near infrared fluorescent dye is such as shown in (b):
The preparation method of the near infrared fluorescent dye the following steps are included:
(1) under condition of ice bath, dense H is being housed2SO4In the 100mL round-bottomed flask of (40mL), N, N- diethyl -3- is added
Hydroxyanilines (4.9573g, 30mmol), being vigorously stirred makes dissolution of raw material, and ice bath is kept to be slowly added to NaNO3(2.805g,
33mmol), 7h is stirred at room temperature, after the reaction was completed, reaction solution is poured slowly into 200mL ice water, a large amount of yellow-brown solids are precipitated,
Decompression filters, and filter cake washs (50mL*3) with deionized water repeatedly, is dried in vacuo.
(2) gained filter cake compound is dissolved in ethyl alcohol (200mL), a small amount of palladium carbon is added and makees catalyst, at room temperature hydrogen
Atmosphere encloses middle reaction, removes hydrogen when reaction solution color becomes colorless, admits air into reaction flask, solution colour becomes rapidly
For blue black color, continues stirring at normal temperature and react 10h, stop reaction, filter out palladium carbon and be evaporated under reduced pressure removing solvent, crude product is through silica gel
Chromatography post separation, eluant, eluent are methylene chloride, obtain target compound, yield 1.17g, yield 27.55%.
The present invention carries out table by nuclear magnetic resonance spectroscopy (Fig. 1), carbon spectrum (Fig. 2) and mass spectrum (Fig. 3), to product structure
Sign determines, the optical property (Fig. 4) of dyestuff is studied by fluorescence emission spectrometry.The core of near infrared fluorescent dye of the invention
Magnetic resonance hydrogen spectrogram is as shown in Figure 1, carbon-13 nmr spectra figure is as shown in Fig. 2, and mass spectrogram is as shown in figure 3, illustrate to have synthesized this hair
Bright near infrared fluorescent dye.
The hydrogen nuclear magnetic resonance spectrogram of near infrared fluorescent dye of the invention as shown in Figure 1,1H NMR(600MHz, CDCl3-
d1): δ (ppm): 7.55 (d, J=9.1,1H), 6.73 (dd, J=9.1,2.7,1H), 6.52 (d, J=2.6,1H), 6.48 (s,
1H), 6.37 (s, 1H), 4.85 (s, 2H), 3.46 (q, J=7.1,4H), 1.25 (t, J=7.1,6H)；Near-infrared of the invention
The carbon-13 nmr spectra figure of fluorescent dye as shown in Fig. 2,13C NMR(150MHz,CDCl3-d1):δ(ppm):179.58,
149.53,149.47,145.66,144.22,142.43,129.89,110.59,103.56,102.20,96.12,45.05,
12.61；Near infrared fluorescent dye of the invention is analyzed by mass spectrometry, mass spectrogram is as shown in figure 3, ESI-MS m/z:[M+H]+
Calcd.for C16H18N3O2 +284.1394；Found 284.1397；Illustrate to have synthesized near infrared fluorescent dye of the invention.
Synthesized dyestuff is configured to the DMSO solution of 2mM, take respectively 5 μ L be added equipped with 2mL different solvents (methanol,
Dimethyl sulfoxide, methylene chloride, tetrahydrofuran, 1,4- dioxane, ethyl alcohol, ethyl acetate, N,N-dimethylformamide, trichlorine
Methane, water, totally ten kinds of solvents) fluorescence cuvette in, exciting slit is set and transmite slit is 2.5nm, research dyestuff exists
Fluorescence emission spectrum in different solvents, as a result as shown in figure 4, illustrating that near infrared fluorescent dye of the invention has fluorescence property
Excellent characteristic.
Comparative example 1
Unique difference of this comparative example and embodiment 3 is that Raney's nickel is used to replace palladium carbon as catalyst, obtains target chemical combination
Object, yield 0.85g, yield 20.11%.Compared with Example 3, reduction efficiency is low, low yield.
Comparative example 2
Unique difference of this comparative example and embodiment 3 is to replace palladium carbon hydrogenation to restore with sodium hydrosulfite adding sodium hydroxide solution
Nitro obtains target compound, yield 0.71g, yield 16.74%.Compared with Example 3, reduction efficiency is low, low yield, and
Liquid waste processing is difficult.
By comparison, illustrate that the palladium carbon that the present invention uses shares reduction nitro as catalyst, and with hydrogen, efficiency is most
Height, subsequent processing is most easy, and energy conservation and environmental protection.
The above description is merely a specific embodiment, but scope of protection of the present invention is not limited thereto, any
Those familiar with the art in the technical scope disclosed by the present invention, can easily think of the change or the replacement, and should all contain
Lid is within protection scope of the present invention.Therefore, protection scope of the present invention should be based on the protection scope of the described claims.
Claims (10)
1. a kind of near infrared fluorescent dye, which is characterized in that the structural formula of the near infrared fluorescent dye is such as shown in (a):
2. the method for preparing near infrared fluorescent dye described in claim 1, which is characterized in that the reaction equation of the method
As shown in (b):
The preparation method of the near infrared fluorescent dye the following steps are included:
(1) to dense H2SO4Middle addition N, N- diethyl -3- hydroxyanilines, stirring make dissolution of raw material, and NaNO is added3, continue to stir
To after the reaction was completed, reaction solution is poured into ice water, a large amount of yellow-brown solids are precipitated, decompression filters, and filter cake is washed with deionized water
It washs, vacuum drying obtains filter cake compound；
(2) the filter cake compound obtained by step (1) is dissolved in ethyl alcohol, is reacted in atmosphere of hydrogen, become to reaction solution color
Hydrogen is removed when being colourless, is admitted air into reaction flask, solution colour becomes blue black color, continues to be stirred to react 9-11h, stops
Reaction；Then vacuum distillation removes solvent and obtains crude product, by the crude product through chromatography post separation, obtains target compound.
3. the preparation method of near infrared fluorescent dye according to claim 2, which is characterized in that described to add in step (1)
Enter NaNO3, the time for continuing stirring is 6-8h.
4. the preparation method of near infrared fluorescent dye according to claim 3, which is characterized in that in step (1), in ice bath
Under the conditions of, to dense H2SO4Middle addition N, N- diethyl -3- hydroxyanilines, stirring make dissolution of raw material, keep ice bath that NaNO is added3,
Room temperature continues stirring 6-8h and after the reaction was completed pours into reaction solution in ice water, and a large amount of yellow-brown solids are precipitated, and decompression filters, filter
Cake is washed repeatedly with deionized water, and at least three times, vacuum drying obtains filter cake compound.
5. the preparation method of near infrared fluorescent dye according to claim 2, which is characterized in that in step (1), the N,
N- diethyl -3- hydroxyanilines and the NaNO3Molar ratio be 29-31:33.
6. the preparation method of near infrared fluorescent dye according to claim 5, which is characterized in that the N, N- diethyl-
3- hydroxyanilines and the NaNO3Molar ratio be 10:11.
7. the preparation method of near infrared fluorescent dye according to claim 6, which is characterized in that every dense H of 40mL2SO4In plus
Enter the N of 30mmol, the NaNO of N- diethyl -3- hydroxyanilines and 33mmol3。
8. the preparation method of near infrared fluorescent dye according to claim 7, which is characterized in that under condition of ice bath, often
The dense H of 40mL2SO4The middle N that 30mmol is added, N- diethyl -3- hydroxyanilines, stirring make dissolution of raw material, and ice bath is kept to be added
The NaNO of 33mmol3, room temperature continues to stir 7h, until after the reaction was completed, reaction solution is poured slowly into 200mL ice water, is precipitated big
Yellow-brown solid is measured, decompression filters, and filter cake is washed repeatedly with deionized water, and at least three times, vacuum drying obtains filter cake compound.
9. the preparation method of near infrared fluorescent dye according to claim 2, which is characterized in that, will be described in step (2)
Filter cake compound is dissolved in ethyl alcohol, and palladium carbon is added as catalyst, reacts in atmosphere of hydrogen at room temperature, becomes to reaction solution color
Hydrogen is removed when being colourless, is admitted air into reaction flask, solution colour becomes blue black color, continues stirring at normal temperature and reacts 10h, stops
Only react；Then it filters out palladium carbon and is evaporated under reduced pressure removing solvent and obtain crude product, by the crude product through chromatography post separation, obtain
Target compound.
10. the preparation method of near infrared fluorescent dye according to claim 8, which is characterized in that the crude product is through silicon
Glue chromatography post separation, eluant, eluent used are methylene chloride.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113603654A (en) * | 2021-07-14 | 2021-11-05 | 江苏大学 | Difunctional fluorescent probe for detecting lipid droplets and/or protein aggregates and preparation method and application thereof |
| CN114394947A (en) * | 2022-01-24 | 2022-04-26 | 中国药科大学 | Oxazine near-infrared fluorescent dye and preparation method and application thereof |
| WO2022199140A1 (en) * | 2021-03-24 | 2022-09-29 | 深圳先进技术研究院 | Lipid droplet targeted fluorescent dye, and preparation method therefor and use thereof |
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| CN105985363A (en) * | 2015-01-29 | 2016-10-05 | 中南大学 | Synthesis and application of fluoro-boron-type fluorescent dye |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2022199140A1 (en) * | 2021-03-24 | 2022-09-29 | 深圳先进技术研究院 | Lipid droplet targeted fluorescent dye, and preparation method therefor and use thereof |
| CN113603654A (en) * | 2021-07-14 | 2021-11-05 | 江苏大学 | Difunctional fluorescent probe for detecting lipid droplets and/or protein aggregates and preparation method and application thereof |
| CN113603654B (en) * | 2021-07-14 | 2022-07-22 | 江苏大学 | Difunctional fluorescent probe for detecting lipid droplets and/or protein aggregates as well as preparation method and application thereof |
| CN114394947A (en) * | 2022-01-24 | 2022-04-26 | 中国药科大学 | Oxazine near-infrared fluorescent dye and preparation method and application thereof |
| CN114394947B (en) * | 2022-01-24 | 2023-10-27 | 中国药科大学 | Oxazine near-infrared fluorescent dye and preparation method and application thereof |
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