CN108410202A - A kind of preparation method of seven methine cyanine dyes of quinoline - Google Patents
A kind of preparation method of seven methine cyanine dyes of quinoline Download PDFInfo
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- CN108410202A CN108410202A CN201810145064.9A CN201810145064A CN108410202A CN 108410202 A CN108410202 A CN 108410202A CN 201810145064 A CN201810145064 A CN 201810145064A CN 108410202 A CN108410202 A CN 108410202A
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- cyanine dyes
- quinoline
- methine cyanine
- infrared
- methine
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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
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/10—The polymethine chain containing an even number of >CH- groups
- C09B23/107—The polymethine chain containing an even number of >CH- groups four >CH- groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
-
- 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
- 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
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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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Quinoline Compounds (AREA)
Abstract
The present invention relates to a kind of seven methine cyanine dyes of near-infrared quinolines and preparation method thereof, belong to chemical industry organic dyestuff synthesis field.The nir dye of synthesis has excellent optical property, is such as in 2nd area of near-infrared, compound Stokes shift is big, and photostability is strong, and synthesis step is short, purifies the advantages that facilitating.The most apparent characteristic of such dyestuff is that have stronger absorption in 2nd area of near-infrared, and excellent penetrability is all had to environment, biological tissue, has very high quantum yield in organic solvent such as dichloromethane.It can be used for biomolecular labeling, the fields such as fluorescence imaging.The probe preparation method is simple and practicable, at low cost, good in economic efficiency, is suitable for industrialized production.
Description
Technical field
The invention belongs to organic dyestuff to synthesize field, and in particular to a kind of preparation method of seven methine cyanine dyes of quinoline.
Background technology
Polymethin cyanine dyestuff is a kind of often using the various heterocycles such as indoles, pyridine, quinoline, thiazole, pyrroles as the fluorescence of end group
Dyestuff.The intramolecule of cyanine dyes contains the conjugated chain of methine (also referred to as methine) composition, and conjugated chain both ends or centre connect
There are heterocycle, aromatic compound, cycloalkene compound etc. with conjugation chain group at a big conjugated system, intramolecular hydrogen can be by one
All kinds of substituent group substitutions of fixed number purpose.Quinoline cyanine dyes is an important branch of cyanine dyes, such dyestuff has higher rub
That extinction coefficient, fluorescence emission wavelengths are easier to adjust and maximum absorption wavelength tunable range is big, is readily synthesized and has opposite
Higher stability.In recent years more answer is obtained in bioprobe field, optical memory material, biomolecular labeling etc.
With.
At present use its maximum absorption wavelength of more quinoline dye and fluorescence emission wavelengths it is shorter, fluoroscopic examination it is sensitive
It spends relatively low.The Absorption and emission spectra area of polymethin cyanine dyestuff is at 700nm-1200nm, in this wide spectrum region, biological context
Fluorescence and the interference for scattering light are all very weak, therefore the signal-to-noise ratio being imaged is high.In addition, such dyestuff photostability is preferable, mole disappear
Backscatter extinction logarithmic ratio is higher, and synthesis technology is simple, can directly apply to the fields such as label or the solar cell of biomolecule, have
Wide application prospect.
Invention content
To solve the above-mentioned problems, longer (900-1200nm) it is an object of the invention to synthesize launch wavelength, it can be effective
It avoids biological context fluorescence from interfering, there is larger stoke shift, molar extinction coefficient is big, the good organic molecule of fluorescence property
Dyestuff.The most apparent characteristic of such dyestuff is that in organic solvent, such as toluene, dichloromethane, ethyl alcohol, absorption maximum can be sent out
Near-infrared fluorescent of the wavelength in 1000-1100nm.Synthetic method of the present invention is simple, and mild condition, yield is higher, is biomolecule
Label, solar cell, the fields such as fluorescence imaging provide good application prospect.
The technical scheme is that：
The present invention provides a kind of synthetic method of seven methine cyanine dyes of near-infrared quinolines, and skeleton symbol is as follows：
Wherein, R=(CH2)nCH3, n=0-14 integers；
R of the present invention is preferably C2-C8Alkyl chain；
The present invention also provides a kind of preparation methods of seven methine cyanine dyes of quinolines, include the following steps：
(1) first quinoline compound is heated to reflux in organic solvent, reaction time 6-48 hour with halogenated alkane, is reacted
After the completion, cooling, reaction solution is poured into ether and is filtered；
(2) by step (1) product and N- [(the chloro- 1- cyclohexene -1- bases of 3- (aniline methylene) -2-) methylene] aniline
Hydrochloride is under acetic acid salt action, the back flow reaction in alcoholic solvent, reaction time 1-48h.
(3) step (2) product is concentrated, by column chromatography purified product, and is recrystallized to give final product in ether.
The quinoline compound isThe halogenated alkane is iodo, bromo, chloro alkyl chain；The alkyl
Chain is C1-C15Alkyl chain.
The preparation method of seven methine cyanine dyes of quinolines according to the present invention, step (1) described reaction dissolvent are preferred
Be acetonitrile.
The preparation method of seven methine cyanine dyes of quinolines according to the present invention, the reaction reflux described in step (1)
Time is 6-48 hours.
The preparation method of seven methine cyanine dyes of quinolines according to the present invention, quinoline described in step (1) with it is halogenated
It is 1 that molar ratio, which is added, in alkane:1-1:2.
The preparation method of seven methine cyanine dyes of quinolines according to the present invention, step (1) the product recrystallization are molten
Agent is ether.
The preparation method of seven methine cyanine dyes of quinolines according to the present invention, step (2) the reaction acetate add
It is sodium acetate or potassium acetate to add agent.
The preparation method of seven methine cyanine dyes of quinolines according to the present invention, step (2) described reaction dissolvent are second
Alcohol.
The preparation method of seven methine cyanine dyes of quinolines according to the present invention, step (2) reaction time are 1-
48 hours.
The preparation method of seven methine cyanine dyes of quinolines according to the present invention, step (3) are described cold after reaction
But, required recrystallization solvent is ether.
The preparation method of seven methine cyanine dyes of quinolines according to the present invention, cyanine dyes are the change having the following structure
Close object.
Alkyl chain
The synthetic route of the preparation method of seven methine cyanine dyes of quinolines according to the present invention is：
Wherein, R C1-C15Alkyl chain.X is iodine, bromine, chlorine.
Seven methine cyanine dyes wavelength of fluorescence of quinolines provided by the invention reaches 1200nm, and changing long alkyl chains will not shadow
Wavelength of fluorescence is rung, different alkyl chains can meet different requirements, keep such application more extensive.
The beneficial technique effect of the present invention：
Seven methine cyanine dyes of quinolines provided by the invention are absorbed for one kind and all longer fluorescent dye of launch wavelength, this
The invention seven methine cyanine dyes fluorescence emission wavelengths of quinolines reach 950-1250nm, and molar extinction coefficient is high, and light is stablized
Property it is good, can be used for marking biomolecule or applied to the fields such as solar cell.The Dyestuff synthesis method is simple, condition temperature
With, yield is very high, have good application prospect.
Description of the drawings
The positions Fig. 1 seven methine cyanine dyes ultraviolet spectra of quinoline of the present invention；
The positions Fig. 2 seven methine cyanine dyes fluorescence spectrum of quinoline of the present invention；
Specific implementation mode
In order to make the purpose , technical scheme and advantage of the present invention be clearer, present invention following specific examples
It illustrates, but the present invention is limited to absolutely not these examples.It is as described below to be only the preferred embodiment of the present invention, it is only used for explaining this
Invention, it cannot be construed as a limitation to the scope of the present invention.It should be pointed out that it is every the present invention spirit and
Any modification, replacement or the improvement made within principle should all be included in the protection scope of the present invention.
Embodiment 1
(1) 3 grams of 4- methylquinolines are weighed in 100 milliliters of flasks, 50 milliliters of dry acetonitriles are added.It is added after to be dissolved
2.26 grams of bromoethanes, mixture react 6 hours under reflux condition.After the completion of reaction, removed under the conditions of vacuum distillation
Most of acetonitrile, product instill in anhydrous ether, there is yellow solid precipitation.It filters, filter cake is added anhydrous ether and washs 3 times, obtains
To clean product, yield 95%.
(2) 0.8 gram of product in step (1) is weighed, [(the chloro- 1- cyclohexene -1- bases of 3- (aniline methylene) -2-) is sub- by N-
Methyl] 0.5 gram of anilinechloride, 0.9 gram of sodium acetate is dissolved in 50 milliliters of ethyl alcohol.After solvent, mixture is in counterflow condition
Lower reaction 12 hours.After complete reaction, solvent is boiled off, product passes through column chromatography (dichloromethane：Methanol=95:5) it purifies, and
It is dissolved in dichloromethane again, final product, yield 85% is obtained by the way that Diethyl ether recrystallization is added.
1H NMR(400MHz,CDCl3)δ(ppm)8.51(d,2H),8.12(d,2H),8.05(d,2H),7.81-7.91
(m,4H),7.59(t,2H),7.41(d,2H),4.34(t,4H),2.81(t,4H),1.76(t,4H),0.92(t,6H)
Ultraviolet maximum absorption band wavelength is 981nm, and fluorescence maximum emission wavelength is 1020nm.
Embodiment 2：
(1) 3 grams of 4- methylquinolines are weighed in 100 milliliters of flasks, 50 milliliters of dry acetonitriles are added.It is added after to be dissolved
3.9 grams of iodoethane, mixture react 6 hours under reflux condition.After the completion of reaction, removed under the conditions of vacuum distillation big
Partial acetonitrile, product instill in anhydrous ether, there is yellow solid precipitation.It filters, filter cake is added anhydrous ether and washs 3 times, obtains
Clean product, yield 96%.
(2) 0.8 gram of product in step (1) is weighed, [(the chloro- 1- cyclohexene -1- bases of 3- (aniline methylene) -2-) is sub- by N-
Methyl] 0.5 gram of anilinechloride, 0.9 gram of sodium acetate is dissolved in 50 milliliters of ethyl alcohol.After solvent, mixture is in counterflow condition
Lower reaction 12 hours.After complete reaction, solvent is boiled off, product passes through column chromatography (dichloromethane：Methanol=95:5) it purifies, and
It is dissolved in dichloromethane again, final product, yield 85% is obtained by the way that Diethyl ether recrystallization is added.
Embodiment 3：
(1) 3 grams of 4- methylquinolines are weighed in 100 milliliters of flasks, 50 milliliters of dry acetonitriles are added.It is added after to be dissolved
5.24 grams of bromododecanes, mixture react 6 hours under reflux condition.After the completion of reaction, under the conditions of vacuum distillation
Most of acetonitrile is removed, product instills in anhydrous ether, there is yellow solid precipitation.It filters, anhydrous ether washing 3 is added in filter cake
It is secondary, obtain clean product, yield 95%.
(2) 0.8 gram of product in step (1) is weighed, [(the chloro- 1- cyclohexene -1- bases of 3- (aniline methylene) -2-) is sub- by N-
Methyl] 0.5 gram of anilinechloride, 0.9 gram of sodium acetate is dissolved in 50 milliliters of ethyl alcohol.After solvent, mixture is in counterflow condition
Lower reaction 12 hours.After complete reaction, solvent is boiled off, product passes through column chromatography (dichloromethane：Methanol=95:5) it purifies, and
It is dissolved in dichloromethane again, final product, yield 87% is obtained by the way that Diethyl ether recrystallization is added.
Embodiment 4：
(1) 3 grams of 4- methylquinolines are weighed in 100 milliliters of flasks, 50 milliliters of dry acetonitriles are added.It is added after to be dissolved
2.26 grams of bromoethanes, mixture react 6 hours under reflux condition.After the completion of reaction, removed under the conditions of vacuum distillation
Most of acetonitrile, product instill in anhydrous ether, there is yellow solid precipitation.It filters, filter cake is added anhydrous ether and washs 3 times, obtains
To clean product, yield 95%.
(2) 0.8 gram of product in step (1) is weighed, [(the chloro- 1- cyclohexene -1- bases of 3- (aniline methylene) -2-) is sub- by N-
Methyl] 0.5 gram of anilinechloride, 0.9 gram of potassium acetate is dissolved in 50 milliliters of ethyl alcohol.After solvent, mixture is in counterflow condition
Lower reaction 12 hours.After complete reaction, solvent is boiled off, product passes through column chromatography (dichloromethane：Methanol=95:5) it purifies, and
It is dissolved in dichloromethane again, final product, yield 85% is obtained by the way that Diethyl ether recrystallization is added.
Embodiment 5：
(1) 3 grams of 4- methylquinolines are weighed in 100 milliliters of flasks, 50 milliliters of dry acetonitriles are added.It is added after to be dissolved
2.26 grams of bromoethanes, mixture react 48 hours under reflux condition.After the completion of reaction, removed under the conditions of vacuum distillation
Most of acetonitrile, product instill in anhydrous ether, there is yellow solid precipitation.It filters, filter cake is added anhydrous ether and washs 3 times, obtains
To clean product, yield 95%.
(2) 0.8 gram of product in step (1) is weighed, [(the chloro- 1- cyclohexene -1- bases of 3- (aniline methylene) -2-) is sub- by N-
Methyl] 0.5 gram of anilinechloride, 0.9 gram of potassium acetate is dissolved in 50 milliliters of ethyl alcohol.After solvent, mixture is in counterflow condition
Lower reaction 12 hours.After complete reaction, solvent is boiled off, product passes through column chromatography (dichloromethane：Methanol=95:5) it purifies, and
It is dissolved in dichloromethane again, final product, yield 90% is obtained by the way that Diethyl ether recrystallization is added.
Embodiment 6：
(1) 3 grams of 4- methylquinolines are weighed in 100 milliliters of flasks, 50 milliliters of dry acetonitriles are added.It is added after to be dissolved
2.26 grams of bromoethanes, mixture react 6 hours under reflux condition.After the completion of reaction, removed under the conditions of vacuum distillation
Most of acetonitrile, product instill in anhydrous ether, there is yellow solid precipitation.It filters, filter cake is added anhydrous ether and washs 3 times, obtains
To clean product, yield 94%.
(2) 0.8 gram of product in step (1) is weighed, [(the chloro- 1- cyclohexene -1- bases of 3- (aniline methylene) -2-) is sub- by N-
Methyl] 0.5 gram of anilinechloride, 0.9 gram of potassium acetate is dissolved in 50 milliliters of ethyl alcohol.After solvent, mixture is in counterflow condition
Lower reaction 48 hours.After complete reaction, solvent is boiled off, product passes through column chromatography (dichloromethane：Methanol=95:5) it purifies, and
It is dissolved in dichloromethane again, final product, yield 88% is obtained by the way that Diethyl ether recrystallization is added.
Claims (10)
1. near-infrared luminous seven methine cyanine dyes of quinoline, general formula of molecular structure are as follows：
Wherein, R=(CH2)nCH3, n=0-14 integers,
Physical property：Bottle green is to black solid, and fusing point is within the scope of 200-400 DEG C.
2. seven methine cyanine dyes of near-infrared luminous quinoline according to claim 1, it is characterised in that：Including synthesizing step as follows
Suddenly
(1) first quinoline compound is heated to reflux in organic solvent with halogenated alkane, reaction time 6-48 hour, it is cooling, it will
Reaction solution is poured into ether and is filtered；
(2) by step (1) product and N- [(the chloro- 1- cyclohexene -1- bases of 3- (aniline methylene) -2-) methylene] aniline hydrochloric acid
Salt is under acetic acid salt action, the back flow reaction in alcoholic solvent, reaction time 1-48h；
(3) step (2) product is concentrated, by column chromatography purified product, and is recrystallized to give final product in ether.
3. seven methine cyanine dyes of near-infrared luminous quinoline according to claim 1, it is characterised in that：Seven first of quinoline
River cyanine dyes is seven methine cyanine dyes of symmetrical quinolines.
4. seven methine cyanine dyes of near-infrared luminous quinoline according to claim 1, it is characterised in that：Described is symmetrical or non-
Symmetrical seven methine cyanine dyes of quinolines, R is alkyl chain in structural formula, and contains 1-15 carbon atom.
5. seven methine cyanine dyes of near-infrared luminous quinoline according to claim 1, it is characterised in that：The symmetrical quinoline
Class near-infrared cyanine dye absorbing wavelength is 700-1100nm.
6. seven methine cyanine dyes of near-infrared luminous quinoline according to claim 1, it is characterised in that：The symmetrical quinoline
Class near-infrared cyanine dye launch wavelength is 900-1400nm.
7. seven methine cyanine dyes of near-infrared luminous quinoline according to claim 1, it is characterised in that：The institute in step (1)
The halogenated alkane stated is alkane iodide or brominated alkanes or chloralkane.
8. seven methine cyanine dyes of near-infrared luminous quinoline according to claim 1, it is characterised in that：The quinoline in step (1)
The ratio of quinoline and N- [(the chloro- 1- cyclohexene -1- bases of 3- (aniline methylene) -2-) methylene] anilinechloride is 2：1.
9. seven methine cyanine dyes of near-infrared luminous quinoline according to claim 1, it is characterised in that：The institute in step (2)
The acetate stated is sodium acetate or potassium acetate.
10. seven methine cyanine dyes of near-infrared luminous quinoline according to claim 1, it is characterised in that：The institute in step (2)
The alcoholic solution stated is ethyl alcohol.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113683562A (en) * | 2021-07-20 | 2021-11-23 | 华东理工大学 | Novel anti-solvent quenching near-infrared two-region dye, and preparation method and application thereof |
| CN114279991A (en) * | 2021-12-30 | 2022-04-05 | 宜宾五粮液股份有限公司 | Method for identifying white spirit brand |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN113683562A (en) * | 2021-07-20 | 2021-11-23 | 华东理工大学 | Novel anti-solvent quenching near-infrared two-region dye, and preparation method and application thereof |
| CN114279991A (en) * | 2021-12-30 | 2022-04-05 | 宜宾五粮液股份有限公司 | Method for identifying white spirit brand |
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Application publication date: 20180817 |
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