CN104164230B - Preparation method of near-infrared organic luminescent material - Google Patents
Preparation method of near-infrared organic luminescent material Download PDFInfo
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Abstract
The invention discloses a preparation method of a novel near-infrared organic luminescent material, which comprises the following steps: A. stirring 2-methyl cyclohexanone or cyclohexanone or cyclopentanone, chalcone, solid potassium hydroxide and benzyltriethylammonium chloride at room temperature to obtain a compound disclosed as chemical general formula 4; B. mixing the compound disclosed as chemical general formula 4 with R1-CHO to prepare a compound disclosed as chemical general formula 6, or mixing a compound 4a with 5 times of 1,4-dihydro-2,6-dimethoxybenzene to obtain a compound 5. After the compound is recrystallized and purified, the yield is greater than 80% and is much higher than the yield in the document. The method has the advantages of reasonable technological design and high yield, and is economical and feasible.
Description
Technical field
The present invention relates to a kind of preparation method of luminous organic material, more particularly, to a kind of organic pyrans or pyridines
The preparation method of luminescent material.
Background technology
Life science develops rapidly, inseparable with molecular recognition technology.Molecular recognition is the basic training of supramolecular system
One of can, by micro-variations between molecule and the molecule conducting out by fluorescence signal that interacts, referred to as fluorescence chemical passes
Sensor molecule.Because this kind of sensor molecule has the superiority such as sensitivity is high, selectivity is good, the response time is short.Therefore in base
Because of the position of sequencing, gene expression, protein labeling and cellular content and the tracking of current intelligence, and cell is carried out
The aspect such as identification and classification is widely used.
In organic optoelectronic and infrared optical fiber field, such as nonlinear optics, optical frequency-doubling, two-photon absorption, letter
The aspect such as breath storage, electroluminescent, solid-state or organic film stimulated radiation be luminous is it is necessary to efficient luminous operation material
Based on.
The absorption of the organic luminescent compounds of commercialization and launch wavelength has focused largely on UV and visible spectra at present
Scope (350-650nm), but can have near-infrared (650-1000nm) biological tissue " window " wavelength of height penetrability
In the range of the product that uses seldom, particularly on more than 1000nm spectral regions can be used for, organic operation material of conversion is just more
Rare.Due to biological tissue in ultraviolet and visible spectrum area (350-650nm) to the high scattering of light and high-absorbable, when with fluorescence
The autofluorescence of some strength can be showed, severe jamming is simultaneously greatly reduced the sensitivity of detection, thus seriously making during technology for detection
About fluorescent technique application in vivo.Scientific circles are it is believed that only in near-infrared biological tissue " window " wave spectrum
Area, the fluorescence analysis with near-infrared luminous organic material as operation material, could really be filled in histocyte body
The application dividing.Because biological tissue absorbs little, fluorescence background interference in near-infrared " window " area, it is negligible, so inspection
There is during survey high sensitivity.
Infrared and near-infrared luminous organic material is that the high-end technology in the supramolecular chemistry field that last decade grows up is produced
Product, species is in great shortage, expensive.Invention more reasonably synthetic method, develops the master that more inexpensive process route is this patent
Syllabus.
Have been developed over the INFRARED ABSORPTION seven methine pyrylium dye (heptamethine of plurality of stable at present
pyrylium dyes).8- [5- (6,7- dihydro -2,4- diphenyl -5H-1- chromene -8- base) -2,4- front three thiazolinyl -2,
4- pentadiene subunit] -5,6,7,8- tetrahydrochysene -2,4- diphenyl -1- chromene perchlorate is exactly one of which, maximum suction
Receipts wavelength is 1090nm, and this compound can serve as nonlinear optics, optical frequency-doubling, laser, two-photon absorption, bioluminescence divide
Conventional operation material and basic luminous organic material in the modern high end technical fields such as analysis.Document J.Org.Chem.,
Vol.42, No.5,1977,885-888 disclose a kind of synthesis 8- [5- (6,7- dihydro -2,4- diphenyl -5H-1- benzo pyrrole
Mutter -8- base) -2,4- front three thiazolinyl -2,4- pentadiene subunit] -5,6,7,8- tetrahydrochysene -2,4- diphenyl -1- chromene is high
The method of chlorate, the yield of the intermediate 2 in the method is very low, is up to 10%, leads to overall yield relatively low, thus affecting
Its extension produces.
By contrast, the pyrans luminescent material of traditional handicraft either five yuan of unsubstituted or hexa-atomic alicyclic ring alkenes
Condensing agent, the end group of associated light compound molecule, and mutually be condensed after final products all there are synthesis technique imperfection, receipts
The low shortcoming of rate.On the basis of with reference to forefathers' research, invent new pyran compounds synthetic method, make manufacturing work
Skill is more reasonable, and effective reduces cost is the main points of the present invention.It is, thus, sought for synthesis technique more economical, that yield is higher, and
The present invention solves this technical problem.
Content of the invention
It is an object of the invention to provide a kind of preparation method of new near-infrared organic luminescent material, mainly pyrans
Or the preparation method of pyridines luminescent material.
The chemical general formula of a kind of organic pyrans or pyridines luminescent material is as follows：
Wherein X is oxygen or N-methyl；R1For 1,3,3- tri-methyl indole quinoline -2- subunit or 3- methylbenzothiazole quinoline -2-
Subunit or 3- methyl benzo oxazoline -2- subunit or 3- methoxyl group -4 hydroxy phenyl or 4- hydroxy phenyl or phenyl are therein arbitrarily
A kind of；N is 0 or 1.
Described X is oxygen, R1For 1,3,3- tri-methyl indole quinoline -2- subunit or 3- methylbenzothiazole quinoline -2- subunit or 3-
Methyl benzo oxazoline -2- subunit or 3- hydroxyl -4- methoxyphenyl or 4- hydroxy phenyl or phenyl therein any one；n
For 1.
Described X is N-methyl, R1For 1,3,3- tri-methyl indole quinoline -2- subunit or 3- methylbenzothiazole quinoline -2- subunit
3- methyl benzo oxazoline -2- subunit or 3- hydroxyl -4- methoxyphenyl or 4- hydroxy phenyl or phenyl therein any one
Kind；N is 1.
Described X is N-methyl, R1For 1,3,3- tri-methyl indole quinoline -2- subunit or 3- methylbenzothiazole quinoline -2- subunit
3- methyl benzo oxazoline -2- subunit or 3- hydroxyl -4- methoxyphenyl or 4- hydroxy phenyl or phenyl therein any one
Kind；N is 0.
A kind of organic pyrans or the preparation method of pyridines luminescent material, comprise the steps：
A. the synthesis formula of chemical general formula 4
By general structure 1, chalcone, solid potassium hydroxide and benzyltriethylammoinium chloride mol ratio 20：10：1.2：
1.2 mixing, wherein n is 0 or 1, R2For hydrogen atom or methyl, reaction 3-4 hour is stirred at room temperature, then reactant liquor chloroform extracts
Take, extract Na2SO4It is dried, after vacuum steams solvent, mother liquor carbon tetrachloride/hexane (3:1) solution stirring mixing, separates out
Precipitation, obtains almost colourless solid product 4-1, yield 80-90% after filtration.Product 4-1 is dissolved in dichloromethane, addition rubs
You form red reaction mixture than the mixed liquor of 1.1 times of first ammonia and acetonitrile, react 12 hours, then reduced pressure concentration reaction mixing
Liquid becomes pasty state, adds absolute ether, so that paste product is mixed with ether, filters.Filter cake ice absolute ethanol washing, does
Product, yield 90% is recrystallized to obtain with absolute ethyl alcohol after dry.
B. the synthesis formula of chemical general formula 5 or 6
Chemical general formula 4 is dissolved in a small amount of pyridine, wherein X is oxygen, R2For methyl, n is 1, then plus 5 times amount Isosorbide-5-Nitrae-dihydro-
After 2,6- dimethoxy benzene mixing, it is warming up to and dissolves each other, after forming reactant mixture, continue stirring 10-15 minute.Successively anhydrous
Pyridine, triethylamine is separately added in reaction mixture, continues to be stirred at reflux 10-15 minute.After stopping heating, sodium perchlorate will be contained
Ethanol solution be added in reactant liquor, be stirred for 10 minutes, after cooling, have Precipitation, filter, use absolute ethanol washing filter cake,
Recrystallized with nitromethane after drying, obtain the glossy powder compounds of aterrimus 5, yield 85%.
By in chemical general formula 4 plus acetic acid, wherein X is oxygen or N-methyl, and n is 0 or 1, R2For hydrogen atom, stirring forms anti-
Answer mixed solution.Then preparing R1-CHO(R1For 3- hydroxyl -4- methoxyphenyl or 4- methoxyphenyl or 4- hydroxy phenyl
Or phenyl), the solution of acetic acid is added in above-mentioned reaction mixture, then drips sulfuric acid, flows back 30 minutes, and cooled and filtered precipitates.
Filter cake is dried after being washed with cold acetic acid, obtains product 6 (R after Recrystallisation from acetic acid1For 3- hydroxyl -4- methoxyphenyl or 4- methoxyl group
Phenyl or 4- hydroxy phenyl or phenyl), yield 80-85%.
Chemical general formula 4 is dissolved in isopropanol/acetonitrile (1：1) in solution, wherein X is oxygen or N-methyl, and n is 0 or 1, R2
For hydrogen atom, stirring formation reaction mixture.Add R1-CHO(R1For 1,3,3- tri-methyl indole quinoline -2- subunit or 3- methyl
Benzothiazoline -2- subunit or 3- methyl benzo oxazoline -2- subunit), after stirring 15-30 minute, cooling, filter precipitation.Filter
Cake ice absolute ethyl alcohol and ice absolute ether wash respectively, are dried, and absolute ethyl alcohol recrystallizes, and obtains compound 6 (R1For 1,3,3- tri-
Methyl indol quinoline -2- subunit or 3- methylbenzothiazole quinoline -2- subunit or 3- methyl benzo oxazoline -2- subunit), yield 90
95%.
Specific embodiment
Example below is used for further describing the present invention, but the invention is not limited in any way.
Embodiment 1
8- [5- (6,7- dihydro -2,4- diphenyl -5H-1- chromene -8- base) -2,4- front three thiazolinyl -2,4- pentadiene
Subunit] -5,6,7,8- tetrahydrochysene -2,4- diphenyl -1- chromene perchlorate compounds (5) synthesis
2,4- diphenyl -8- methyl -5,6,7,8- tetrahydrochysene -1- chromene perchlorate 4a (wherein X is oxygen, and n is 1,
R2For methyl) (1mmol), be first dissolved in a small amount of pyridine, then plus Isosorbide-5-Nitrae-dihydro -2,6- dimethoxy benzene (5mmol) mixing after, rise
Temperature, to dissolving each other, after forming reactant mixture, continues stirring 10-30 minute.Successively anhydrous pyridine 5ml, triethylamine (5mmol) point
Jia Ru not continue to be stirred at reflux 10-30 minute in reaction mixture.After stopping heating, the ethanol solution containing sodium perchlorate is added
To in reactant liquor, it is stirred for 10 minutes, after cooling, has Precipitation, filter, use absolute ethanol washing filter cake, after being dried, use nitro
Methane recrystallizes, and obtains the glossy powder of aterrimus, yield 85%.290-291 DEG C of fusing point, decomposes (nitromethane).
Elementary analysis：C50H43ClO6Calculated value %：C 77.5；H 5.6
Test value %：C 77.4；H 5.4
Embodiment 2
8-'s (4- benzylidene) -5,6,7,8- tetrahydrochysene -2,4- diphenyl -1- chromene perchlorate (6a)
Synthesis
By 2,4- diphenyl -5, (wherein X is oxygen to 6,7,8- tetrahydrochysene -1- chromene perchlorate 4b, and n is 1, R2For
Hydrogen) in (4mmol) plus acetic acid 8ml, stirring forms reaction mixture.Then the 4-methoxybenzaldehyde (4mmol) preparing,
The solution of acetic acid 3ml is added in above-mentioned reaction mixture, then drips sulfuric acid 0.7-1ml, and flow back 30-50 minute, cooled and filtered
Precipitation.Filter cake is dried after being washed with cold acetic acid, obtains product, yield 85% after Recrystallisation from acetic acid.Fusing point：223-224℃.
Elementary analysis：C29H25ClO6Calculated value %：C 68.98；H 4.96
Test value %：C 69.03；H 5.04
With reference to the synthetic method of compound 6a described in the present embodiment, respectively with 3- methoxyl group -4 hydroxy benzaldehyde, to hydroxyl
Benzaldehyde, benzaldehyde replace 4-methoxybenzaldehyde to be reacted, and obtain compound 6b, 6c, 6d.
Embodiment 3
1- methyl -2,4- diphenyl -8- [2- (1,3,3- trimethyl indoline -2- subunit) vinyl] -5,6,7,8-
The synthesis of tetrahydroquinoline perchlorate (6e)
Under agitation, in isopropanol and acetonitrile (volume ratio 1:1), in mixed solution, 2,4- diphenyl -5 are added,
(wherein X is N-methyl to 6,7,8- tetrahydrochysene -1- chromene perchlorate 4c, and n is 1, R2For hydrogen) (2.5mmol), Ran Houjia
Heat to dissolving formed reaction mixture, then plus (1,3,3- tri-methyl indole quinoline -2- subunit)-formaldehyde (2.5mmol), stir 15-
After 30 minutes, filtration product precipitates.Filter cake ice absolute ethyl alcohol and ice absolute ether wash respectively, use absolute ethyl alcohol weight after being dried
Crystallization, yield 95%, 203-204 DEG C of fusing point.
Elementary analysis：C35H35ClN2O4Calculated value %：Cl 6.1；N 4.8
Test value %：Cl 6.1；N 5.0
With reference to the synthetic method of compound 6e described in the present embodiment, (3- methylbenzothiazole quinoline -2- subunit)-first respectively
Aldehyde or (3- methyl benzo oxazoline -2- subunit)-formaldehyde, to be reacted, obtain compound 6f, 6g.
Embodiment 4
3- methyl -2- { 2- (2,4- diphenyl -5,6,7,8- tetrahydrochysene cyclohexadiene simultaneously [b] pyrans -7- base) vinyl }-benzene
And the synthesis of thiazole perchlorate 6h
Under agitation, in isopropanol and acetonitrile (volume ratio 1:1) in mixed solution, by 2,4- diphenyl -5,6,
(wherein X is oxygen to 7,8- tetrahydrochysene -1- chromene perchlorate 4b, and n is 1, R2For hydrogen) (2.5mmol) mutually mix, Ran Houjia
Heat to dissolving formed reaction mixture, then plus (3- methylbenzothiazole quinoline -2- subunit)-formaldehyde (2.5mmol), stir 15-30
After minute, filtration product precipitates.Filter cake ice absolute ethyl alcohol and ice absolute ether wash respectively, are tied with absolute ethyl alcohol after being dried again
Crystalline substance obtains product 6h, yield 90%, 269-270 DEG C of fusing point.
Elementary analysis：C31H26O5NClS calculated value %：C66.49；H4.64
Test value %：C 66.70；H4.63
With reference to the synthetic method of compound 6h described in the present embodiment, (3- methyl benzo oxazoline -2- subunit)-first respectively
Aldehyde (1,3,3- tri-methyl indole quinoline -2- subunit)-formaldehyde, to be reacted, obtains compound 6i, 6j.
Embodiment 5
2,4- diphenyl -8- [2- (1,3,3- trimethyl-indoline -2- subunit) vinyl] -6,7- dihydro -5H- ring
The synthesis of pentadiene simultaneously [b] pyrans perchlorate 6k
Under agitation, in isopropanol and acetonitrile (volume ratio 1:1), in mixed solution, 6,7- dihydro -2,4- are added
(wherein X is oxygen to diphenyl -5H- cyclopenta [b] pyrans perchlorate 4d, and n is 0, R2For hydrogen) (2.5mmol), then
Be heated to dissolving formed reaction mixture, then plus (1,3,3- tri-methyl indole quinoline -2- subunit)-formaldehyde (2.5mmol), stirring
After 15-30 minute, filtration product precipitates.Filter cake ice absolute ethyl alcohol and ice absolute ether wash respectively, use anhydrous second after being dried
Alcohol recrystallizes, and obtains product 6k, yield 95%, 245-247 DEG C of fusing point.
Elementary analysis：C33H30ClNO5Calculated value %：Cl 6.2；N 2.5
Test value %：Cl 6.5；N 2.6
With reference to the synthetic method of compound 6k described in the present embodiment, (3- methylbenzothiazole quinoline -2- subunit)-first respectively
Aldehyde or (3- methyl benzo oxazoline -2- subunit)-formaldehyde, to be reacted, obtain compound 6l, 6m.
Above one embodiment of the present of invention is described in detail, but described content has been only the preferable enforcement of the present invention
Example is it is impossible to be considered the practical range for limiting the present invention.All impartial changes made according to the present patent application scope and improvement
Deng all should still belong within the patent covering scope of the present invention.
Claims (1)
1. a kind of organic pyrans or pyridines luminescent material preparation method it is characterised in that：Comprise the steps：
A. the synthesis of chemical general formula 4
Wherein n is 0 or 1, R2For hydrogen or methyl；
B. the synthesis of compound 5 or chemical general formula 6
By chemical general formula 4It is dissolved in a small amount of pyridine, wherein X is oxygen, R2For methyl, n is 1, then plus 5 times
Amount Isosorbide-5-Nitrae-dihydro -2, after the mixing of 6- dimethoxy benzene, are warming up to and dissolve each other, and after forming reactant mixture, continue stirring 10-15 and divide
Clock；Successively anhydrous pyridine, triethylamine is separately added in reaction mixture, continues to be stirred at reflux 10-15 minute；Stop heating
Afterwards, the ethanol solution containing sodium perchlorate is added in reactant liquor, is stirred for 10 minutes, after cooling, have Precipitation, filter, with no
Water-ethanol washs filter cake, with nitromethane recrystallization after being dried, obtains the glossy powder compounds of aterrimus 5,8- [5- (6,7- bis-
Hydrogen -2,4- diphenyl -5H-1- chromene -8- base) -2,4- front three thiazolinyl -2,4- pentadiene subunit] -5,6,7,8- tetrahydrochysene -
2,4- diphenyl -1- chromene perchlorateYield 85%；
By chemical general formula 4Plus in acetic acid, wherein X is oxygen or N-methyl, n is 0 or 1, R2Former for hydrogen
Son, stirring forms reaction mixture；Then preparing R1- CHO, the solution of acetic acid is added in above-mentioned reaction mixture, then drips
Plus sulfuric acid, flow back 30 minutes, cooled and filtered precipitates；Filter cake is dried after being washed with cold acetic acid, obtains chemistry logical after Recrystallisation from acetic acid
Formula 6Yield 80-85%；Wherein R1For 1,3,3- tri-methyl indole quinoline -2- subunit or 3- methyl benzo thiophene
In oxazoline -2- subunit or 3- methyl benzo oxazoline -2- subunit or 3- methoxyl group -4- hydroxy phenyl or 4- hydroxy phenyl or phenyl
Any one.
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