CN104164230A - Preparation method of novel near-infrared organic luminescent material - Google Patents
Preparation method of novel 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, relate in particular to the preparation method of a kind of organic pyrans or pyridines luminescent material.
Background technology
Life science develop rapidly, inseparable with molecular recognition technology.Molecular recognition is one of basic function of supramolecular system, by micro-variations between molecule and the molecule that conducts out by fluorescent signal that interacts, is called fluoescence chemical sensor molecule.Because this class sensor molecule has the superiority such as highly sensitive, selectivity good, the time of response is short.Therefore in the position of gene sequencing, genetic expression, protein labeling and cellular content and the tracking of current intelligence, and cell is identified and the aspect such as classification is widely used.
Learn and infrared optical fiber field at organic optoelectronic, the aspect such as luminous in nonlinear optics, optical frequency-doubling, two-photon absorption, information storage, electroluminescent, solid-state or organic film stimulated radiation, all must be taking high efficiency luminous operation material as basic.
Absorption and the emission wavelength of commercial organic light emission compound concentrate on UV and visible spectra scope (350-650nm) mostly at present, but the product that can use near infrared (650-1000nm) biological tissue " window " wavelength region with height penetrance is little, the organic operation material that particularly can be used for conversion in the above spectral region of 1000nm is just more rare.Because biological tissue is in ultraviolet and compose as seen (350-650nm) high scattering and high-absorbable to light in district, in the time detecting by fluorescence technique, can show the autofluorescence of some strength, severe jamming also significantly reduces the sensitivity detecting, thereby seriously restricts fluorescence technique application in vivo.Scientific circles generally believe, only in near-infrared biological tissue " window " wave spectrum district, the fluorescence analysis taking near infrared luminous organic material as operation material could really be applied fully in histocyte body.Because it is little that biological tissue absorbs near infrared " window " district, fluorescence background disturbs, negligible, so have high sensitivity while detection.
Infrared and near infrared luminous organic material is the high-end technology product in the supramolecular chemistry field that grows up for nearly ten years, and kind is in great shortage, expensive.Invent more rational synthetic method, exploitation more cheaply operational path is the main purpose of this patent.
The infrared absorption seven methine pyrylium dyes (heptamethine pyrylium dyes) of plurality of stable are developed at present.8-[5-(6,7-dihydro-2,4-phenylbenzene-5H-1-chromene-8-yl)-2,4-front three thiazolinyl-2,4-pentadiene subunit]-5,6,7,8-tetrahydrochysene-2,4-phenylbenzene-1-chromene perchlorate is exactly wherein a kind of, maximum absorption wavelength is 1090nm, and this compound can be used as conventional operation material and basic luminous organic material in the modern high end technical fields such as nonlinear optics, optical frequency-doubling, laser, two-photon absorption, fluorimetric assay for biological materials.Document J.Org.Chem., Vol.42, No.5,1977,885-888 discloses a kind of synthetic 8-[5-(6,7-dihydro-2,4-phenylbenzene-5H-1-chromene-8-yl)-2,4-front three thiazolinyl-2,4-pentadiene subunit]-5,6,7,8-tetrahydrochysene-2, the method of 4-phenylbenzene-1-chromene perchlorate, the productive rate of the intermediate 2 in the method is very low, is up to 10%, cause overall yield lower, produce thereby affect its extension.
By contrast, no matter the pyrans luminescent material of traditional technology is five yuan of unsubstituted or the condensing agent of hexa-atomic alicyclic alkene class, the end group of relevant luminophor molecule, and the finished product after phase condensation all exist the shortcomings such as synthesis technique imperfection, yield are low.On the basis with reference to forefathers' research, invent new pyran compounds synthetic method, make manufacturing process more reasonable, effectively reducing costs is main points of the present invention.Therefore, need to find the synthesis technique more economical, yield is higher, and the invention solves this technical problem.
Summary of the invention
The object of this invention is to provide a kind of preparation method of novel near infrared organic luminescent material, is mainly the preparation method of pyrans or 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-formyl sarcolysine base; R
1for 8-(5-(6,7-dihydro-2,4-phenylbenzene-5H-1-chromene-8-yl)-2,4-front three thiazolinyl-2,4-pentadiene subunit) or 2-(3-methylbenzothiazole) vinyl or 2-(3-Jia base benzoxazole) vinyl or 2-(1,3,3-tri-methyl indole) wherein any one of vinyl or 3-methoxyl group-4-hydroxy phenyl or 4-hydroxy phenyl or phenyl; N is 0 or 1.
Described X is oxygen, R
1for 8-(5-(6,7-dihydro-2,4-phenylbenzene-5H-1-chromene-8-yl)-2,4-front three thiazolinyl-2,4-pentadiene subunit) or 2-(3-methylbenzothiazole) vinyl or 2-(3-Jia base benzoxazole) vinyl or 2-(1,3,3-tri-methyl indole) wherein any one of vinyl or 3-hydroxyl-4-p-methoxy-phenyl or 4-p-methoxy-phenyl or 4-hydroxy phenyl or phenyl; N is 1.
Described X is n-formyl sarcolysine base, R
1for 8-(5-(6,7-dihydro-2,4-phenylbenzene-5H-1-chromene-8-yl)-2,4-front three thiazolinyl-2,4-pentadiene subunit) or 2-(3-methylbenzothiazole) vinyl or 2-(3-Jia base benzoxazole) vinyl or 2-(1,3,3-tri-methyl indole) wherein any one of vinyl or 3-hydroxyl-4-p-methoxy-phenyl or 4-p-methoxy-phenyl or 4-hydroxy phenyl or phenyl; N is 1.
Described X is n-formyl sarcolysine base, R
1for 8-(5-(6,7-dihydro-2,4-phenylbenzene-5H-1-chromene-8-yl)-2,4-front three thiazolinyl-2,4-pentadiene subunit) or 2-(3-methylbenzothiazole) vinyl or 2-(3-Jia base benzoxazole) vinyl or 2-(1,3,3-tri-methyl indole) wherein any one of vinyl or 3-hydroxyl-4-p-methoxy-phenyl or 4-p-methoxy-phenyl or 4-hydroxy phenyl or phenyl; N is 0.
A preparation method for organic pyrans or pyridines luminescent material, comprises the steps:
A. the synthetic general formula of chemical general formula 4
General structure 1, chalone, solid potassium hydroxide and benzyltriethylammoinium chloride mol ratio 20:10:1.2:1.2 are mixed, and wherein n is 0 or 1, R
2for hydrogen atom or methyl, stirring at room temperature reaction 3-4 hour, then reaction solution chloroform extraction, extraction liquid Na
2sO
4dry, vacuum steams after solvent, and tetracol phenixin/hexane for mother liquor (3:1) solution stirring is mixed, and separates out precipitation, after filtering, obtains almost colourless solid phase prod 4-1, yield 80-90%.Product 4-1 is dissolved in to methylene dichloride, adds the mixed solution of 1.1 times of first ammonia of mol ratio and acetonitrile to form red reaction mixture, react 12 hours, then concentrating under reduced pressure reaction mixture becomes pasty state, add again anhydrous diethyl ether, pasty state product is mixed with ether, filter.Filter cake ice absolute ethanol washing, obtains product, yield 90% with dehydrated alcohol recrystallization after being dried.
B. the synthetic general formula of chemical general formula 5 or 6
Chemical general formula 4 is dissolved in a small amount of pyridine, and wherein X is oxygen, R
2for methyl, n is 1, then adds 5 times of amount Isosorbide-5-Nitrae-dihydro-2, and 6-dimethoxy benzene is warming up to and dissolves each other after mixing, and forms after reaction mixture, continues to stir 10-15 minute.Anhydrous pyridine, triethylamine adds respectively in reaction mixture successively, continues stirring and refluxing 10-15 minute.Stop, after heating, the ethanolic soln containing sodium perchlorate being added in reaction solution, then stirring 10 minutes, after cooling, have Precipitation, filter, use absolute ethanol washing filter cake, after being dried, use Nitromethane 99Min. recrystallization, obtain the glossy powder compounds 5 of aterrimus, yield 85%.
Chemical general formula 4 is added in acetic acid, and wherein X is oxygen or n-formyl sarcolysine base, and n is 0 or 1, R
2for hydrogen atom, stir and form reaction mixture.Then preparing R
1-CHO (R
1for 3-hydroxyl-4-p-methoxy-phenyl or 4-p-methoxy-phenyl or 4-hydroxy phenyl or phenyl), the solution of acetic acid is added in above-mentioned reaction mixture, then drips sulfuric acid, reflux 30 minutes, cooled and filtered precipitation.Filter cake, with dry after cold acetic acid washing, obtains product 6 (R after acetic acid recrystallization
1for 3-hydroxyl-4-p-methoxy-phenyl or 4-p-methoxy-phenyl or 4-hydroxy phenyl or phenyl), yield 80-85%.
Chemical general formula 4 is dissolved in Virahol/acetonitrile (1:1) solution, and wherein X is oxygen or n-formyl sarcolysine base, and n is 0 or 1, R
2for hydrogen atom, stir and form reaction mixture.Add again R
1-CHO (R
1for 2-(3-methylbenzothiazole)-acetaldehyde or 2-(3 Jia base benzoxazole)-acetaldehyde or 2-(1,3,3-tri-methyl indole)-acetaldehyde), stir after 15-30 minute, cooling, filtering-depositing.Filter cake washs respectively with ice dehydrated alcohol and ice anhydrous diethyl ether, and dry, dehydrated alcohol recrystallization, obtains product 6 (R
1for 2-(3-methylbenzothiazole)-acetaldehyde or 2-(3 Jia base benzoxazole)-acetaldehyde or 2-(1,3,3-tri-methyl indole)-acetaldehyde), yield 90-95%.
Embodiment
Embodiment is used for further describing the present invention below, but does not limit in any form the present invention.
Embodiment 1
8-[5-(6,7-dihydro-2,4-phenylbenzene-5H-1-chromene-8-yl)-2,4-front three thiazolinyl-2,4-pentadiene subunit]-5,6,7,8-tetrahydrochysene-2,4-phenylbenzene-1-chromene perchlorate compound (5) synthetic
2,4-phenylbenzene-8-methyl-5, (wherein X is oxygen to 6,7,8-tetrahydrochysene-1-chromene perchlorate 4a, and n is 1, R
2for methyl) (1mmol), be first dissolved in a small amount of pyridine, then add Isosorbide-5-Nitrae-dihydro-2,6-dimethoxy benzene (5mmol) is warming up to and dissolves each other after mixing, and forms after reaction mixture, continues to stir 10-30 minute.Anhydrous pyridine 5ml, triethylamine (5mmol) adds respectively in reaction mixture successively, continues stirring and refluxing 10-30 minute.Stop, after heating, the ethanolic soln containing sodium perchlorate being added in reaction solution, then stirring 10 minutes, after cooling, have Precipitation, filter, use absolute ethanol washing filter cake, after being dried, use Nitromethane 99Min. recrystallization, obtain the glossy powder of aterrimus, yield 85%.Fusing point 290-291 DEG C, decomposes (Nitromethane 99Min.).
Ultimate analysis: C
50h
43clO
6calculated value %:C77.5; H5.6
Test value %:C77.4; H5.4
Embodiment 2
8-(4-methoxyl group benzylidene)-5,6,7,8-tetrahydrochysene-2,4-phenylbenzene-1-chromene perchlorate (6a) synthetic
By 2,4-phenylbenzene-5, (wherein X is oxygen to 6,7,8-tetrahydrochysene-1-chromene perchlorate 4b, and n is 1, R
2for hydrogen) (4mmol) add in acetic acid 8ml, stir and form reaction mixture.Then the 4-methoxybenzaldehyde preparing (4mmol), the solution of acetic acid 3ml is added in above-mentioned reaction mixture, then drips sulfuric acid 0.7-1ml, backflow 30-50 minute, cooled and filtered precipitation.Filter cake, with dry after cold acetic acid washing, obtains product after acetic acid recrystallization, yield 85%.Fusing point: 223-224 DEG C.
Ultimate analysis: C
29h
25clO
6calculated value %:C68.98; H4.96
Test value %:C69.03; H5.04
With reference to the synthetic method of the 6a of compound described in the present embodiment, replace 4-methoxybenzaldehyde to react with 3-methoxyl group-4 hydroxy benzaldehyde, p-Hydroxybenzaldehyde, phenyl aldehyde respectively, obtain compound 6b, 6c, 6d.
Embodiment 3
1-methyl-2,4-phenylbenzene-8-[2-(1,3,3-trimethylammonium indoline-2-subunit) vinyl]-5,6,7,8-tetrahydroquinoline perchlorate (6e) synthetic
Under agitation condition, in the mixing solutions of Virahol and acetonitrile (volume ratio 1:1), add 2,4-phenylbenzene-5, (wherein X is n-formyl sarcolysine base to 6,7,8-tetrahydrochysene-1-chromene perchlorate 4c, and n is 1, R
2for hydrogen) (2.5mmol), be then heated to dissolve formation reaction mixture, then add (1,3,3-trimethylammonium-1,3-dihydro-indoles-2-subunit)-acetaldehyde (2.5mmol), stir after 15-30 minute filtration product precipitation.Filter cake washs respectively with ice dehydrated alcohol and ice anhydrous diethyl ether, after being dried, uses dehydrated alcohol recrystallization, yield 95%, fusing point 203-204 DEG C.
Ultimate analysis: C
35h
35clN
2o
4calculated value %:Cl6.1; N4.8
Test value %:Cl6.1; N5.0
With reference to the synthetic method of the 6e of compound described in the present embodiment, (3-methyl-3 hydrogen-benzoxazoles-2-subunit)-acetaldehyde, (3-methyl-3 hydrogen-benzothiazole-2-subunit)-acetaldehyde, to react, obtain compound 6f, 6g respectively.
Embodiment 4
3-methyl-2-{2-(2,4-phenylbenzene-5,6,7,8-tetrahydrochysene cyclohexadiene is [b] pyrans-7-yl also) vinyl }-benzothiazole perchlorate 6h synthetic
Under agitation condition, in the mixing solutions of Virahol and acetonitrile (volume ratio 1:1), by 2,4-phenylbenzene-5, (wherein X is oxygen to 6,7,8-tetrahydrochysene-1-chromene perchlorate 4b, and n is 1, R
2for hydrogen) (2.5mmol) mix mutually, be then heated to dissolve formation reaction mixture, then add (3-methyl-3 hydrogen-benzothiazole-2-subunit)-acetaldehyde (2.5mmol), stir after 15-30 minute filtration product precipitation.Filter cake washs respectively with ice dehydrated alcohol and ice anhydrous diethyl ether, after being dried, obtains product 6h, yield 90%, fusing point 269-270 DEG C with dehydrated alcohol recrystallization.
Ultimate analysis: C
31h
26o
5nClS calculated value %:C66.49; H4.64
Test value %:C66.70; H4.63
With reference to the synthetic method of the 6h of compound described in the present embodiment, (3-methyl-3 hydrogen-benzoxazoles-2-subunit)-acetaldehyde, (1,3,3-trimethylammonium-1 respectively, 3-dihydro-indoles-2-subunit)-acetaldehyde to be to react, and obtains compound 6i, 6j.
Embodiment 5
2,4-phenylbenzene-8-[2-(1,3,3-trimethylammonium-indoline-2-subunit) vinyl]-6,7-dihydro-5H-cyclopenta [b] pyrans perchlorate 6k's is synthetic
Under agitation condition, in the mixing solutions of Virahol and acetonitrile (volume ratio 1:1), add 6,7-dihydro-2, (wherein X is oxygen to 4-phenylbenzene-5H-cyclopenta [b] pyrans perchlorate 4d, and n is 0, R
2for hydrogen) (2.5mmol), be then heated to dissolve formation reaction mixture, then add (1,3,3-trimethylammonium-1,3-dihydro-indoles-2-subunit)-acetaldehyde (2.5mmol), stir after 15-30 minute filtration product precipitation.Filter cake washs respectively with ice dehydrated alcohol and ice anhydrous diethyl ether, and the dry rear dehydrated alcohol recrystallization of using, obtains product 6k, yield 95%, fusing point 245-247 DEG C.
Ultimate analysis: C
33h
30clNO
5calculated value %:Cl6.2; N2.5
Test value %:Cl6.5; N2.6
With reference to the synthetic method of the 6k of compound described in the present embodiment, (3-methyl-3 hydrogen-benzoxazoles-2-subunit)-acetaldehyde, (3-methyl-3 hydrogen-benzothiazole-2-subunit)-acetaldehyde, to react, obtain compound 6l, 6m respectively.
Above one embodiment of the present of invention are had been described in detail, but described content is only preferred embodiment of the present invention, can not be considered to for limiting practical range of the present invention.All equalization variation and improvement etc. of doing according to the present patent application scope, within all should still belonging to patent covering scope of the present invention.
Claims (5)
1. the chemical general formula of an organic pyrans or pyridines luminescent material is as follows:
Wherein X is oxygen or n-formyl sarcolysine base; R
1for 8-(5-(6,7-dihydro-2,4-phenylbenzene-5H-1-chromene-8-yl)-2,4-front three thiazolinyl-2,4-pentadiene subunit) or 2-(3-methylbenzothiazole) vinyl or 2-(3-Jia base benzoxazole) vinyl or 2-(1,3,3-tri-methyl indole) wherein any one of vinyl or 3-methoxyl group-4-hydroxy phenyl or 4-hydroxy phenyl or phenyl; N is 0 or 1.
2. organic pyrans according to claim 1 or pyridines luminescent material, is characterized in that: described X is oxygen, R
1for 8-(5-(6,7-dihydro-2,4-phenylbenzene-5H-1-chromene-8-yl)-2,4-front three thiazolinyl-2,4-pentadiene subunit) or 2-(3-methylbenzothiazole) vinyl or 2-(3-Jia base benzoxazole) vinyl or 2-(1,3,3-tri-methyl indole) wherein any one of vinyl or 3-hydroxyl-4-p-methoxy-phenyl or 4-p-methoxy-phenyl or 4-hydroxy phenyl or phenyl; N is 1.
3. organic pyrans according to claim 1 or pyridines luminescent material, is characterized in that: described X is n-formyl sarcolysine base, R
1for 8-(5-(6,7-dihydro-2,4-phenylbenzene-5H-1-chromene-8-yl)-2,4-front three thiazolinyl-2,4-pentadiene subunit) or 2-(3-methylbenzothiazole) vinyl or 2-(3-Jia base benzoxazole) vinyl or 2-(1,3,3-tri-methyl indole) wherein any one of vinyl or 3-hydroxyl-4-p-methoxy-phenyl or 4-p-methoxy-phenyl or 4-hydroxy phenyl or phenyl; N is 1.
4. organic pyrans according to claim 1 or pyridines luminescent material, is characterized in that: described X is n-formyl sarcolysine base, R
1for 8-(5-(6,7-dihydro-2,4-phenylbenzene-5H-1-chromene-8-yl)-2,4-front three thiazolinyl-2,4-pentadiene subunit) or 2-(3-methylbenzothiazole) vinyl or 2-(3-Jia base benzoxazole) vinyl or 2-(1,3,3-tri-methyl indole) wherein any one of vinyl or 3-hydroxyl-4-p-methoxy-phenyl or 4-p-methoxy-phenyl or 4-hydroxy phenyl or phenyl; N is 0.
5. a preparation method for organic pyrans claimed in claim 1 or pyridines luminescent material, comprises the steps:
A. chemical general formula 4
synthetic general formula
By general structure
chalone, solid potassium hydroxide and benzyltriethylammoinium chloride mol ratio 20:10:1.2:1.2 mix, and wherein n is 0 or 1, R
3for hydrogen atom or methyl, stirring at room temperature reaction 3-4 hour, then reaction solution chloroform extraction, extraction liquid Na
2sO
4dry, vacuum steams after solvent, and tetracol phenixin/hexane for mother liquor (3:1) solution stirring is mixed, and separates out precipitation, after filtering, obtains almost colourless solid phase prod 4-1, yield 80-90%.Product 4-1 is dissolved in to methylene dichloride, adds the mixed solution of 1.1 times of first ammonia of mol ratio and acetonitrile to form red reaction mixture, react 12 hours, then concentrating under reduced pressure reaction mixture becomes pasty state, add again anhydrous diethyl ether, pasty state product is mixed with ether, filter.Filter cake ice absolute ethanol washing, obtains product, yield 90% with dehydrated alcohol recrystallization after being dried;
B. the synthetic general formula of chemical general formula 5 or 6
By chemical general formula
be dissolved in a small amount of pyridine, wherein X is oxygen, R
2for methyl, n is 1, then adds 5 times of amount Isosorbide-5-Nitrae-dihydro-2, and 6-dimethoxy benzene is warming up to and dissolves each other after mixing, and forms after reaction mixture, continues to stir 10-15 minute.Anhydrous pyridine, triethylamine adds respectively in reaction mixture successively, continues stirring and refluxing 10-15 minute.Stop, after heating, the ethanolic soln containing sodium perchlorate being added in reaction solution, then stirring 10 minutes, after cooling, have Precipitation, filter, use absolute ethanol washing filter cake, after being dried, use Nitromethane 99Min. recrystallization, obtain the glossy powder compounds 5 of aterrimus, yield 85%;
By chemical general formula
add in acetic acid, wherein X is oxygen or n-formyl sarcolysine base, and n is 0 or 1, R
2for hydrogen atom or methyl, stir and form reaction mixture.Then preparing R
1-CHO, the solution of acetic acid is added in above-mentioned reaction mixture, then drips sulfuric acid, reflux 30 minutes, cooled and filtered precipitation.Filter cake, with dry after cold acetic acid washing, obtains product 6, yield 80-85% after acetic acid recrystallization.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104557840A (en) * | 2014-12-31 | 2015-04-29 | 天津智达慧远商务咨询有限公司 | Method for preparing symmetric organic pyrylium luminescent material |
| CN108659568A (en) * | 2018-06-19 | 2018-10-16 | 清华大学 | The preparation method of hemicyanine dye and the application in photoacoustic imaging |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002034841A1 (en) * | 2000-10-27 | 2002-05-02 | Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo | Light resistance improver |
| JP2005131813A (en) * | 2003-10-28 | 2005-05-26 | Ricoh Co Ltd | Write-once type optical recording medium corresponding to short wavelength |
| EP1792605A1 (en) * | 2005-11-30 | 2007-06-06 | L'Oréal | Use of at least a cationic cyanine derivative for use in hair dyeing, composition containg it process of treating keratinic fibres using the same composition, kit and use thereof |
| CN103038309A (en) * | 2010-06-29 | 2013-04-10 | 辛诺拉有限公司 | Singlet harvesting with organic molecules for optoelectronic devices |
-
2014
- 2014-08-15 CN CN201410403668.0A patent/CN104164230B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002034841A1 (en) * | 2000-10-27 | 2002-05-02 | Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo | Light resistance improver |
| JP2005131813A (en) * | 2003-10-28 | 2005-05-26 | Ricoh Co Ltd | Write-once type optical recording medium corresponding to short wavelength |
| EP1792605A1 (en) * | 2005-11-30 | 2007-06-06 | L'Oréal | Use of at least a cationic cyanine derivative for use in hair dyeing, composition containg it process of treating keratinic fibres using the same composition, kit and use thereof |
| CN103038309A (en) * | 2010-06-29 | 2013-04-10 | 辛诺拉有限公司 | Singlet harvesting with organic molecules for optoelectronic devices |
Non-Patent Citations (4)
| Title |
|---|
| G. A. REYNOLDS ET AL.，: ""Stable Heptamethine Pyrylium Dyes That Absorb in the Infrared"", 《J. ORG. CHEM.》, vol. 42, no. 5, 31 December 1977 (1977-12-31), pages 885 - 888 * |
| L. KARGAPOLOVA ER AL.，: ""Reactions with Methylamine of Pyrilo-2-cyanines Containing Polyfluorophenyl Substituents"", 《RUSSIAN JOURNAL OF ORGANIC CHEMISTRY》 * |
| M. M. EVSTIFEEV ET AL.，: ""Polarographic study of pyrylium salts. I. Oscillopolarographic behavior of some pyrylium salts in acid solutions"", 《ZHURNAL OBSHCHEI KHIMII》, vol. 44, no. 3, 31 December 1974 (1974-12-31), pages 657 - 662 * |
| M.J. íAN DER MEER ET AL.，: ""Femto- and picosecond fluorescence studies of solvation and non-radiative deactivation of ionic styryl dyes in liquid solution"", 《CHEMICAL PHYSICS LETTERS》, vol. 320, no. 56, 14 April 2000 (2000-04-14), pages 673 - 680 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104557840A (en) * | 2014-12-31 | 2015-04-29 | 天津智达慧远商务咨询有限公司 | Method for preparing symmetric organic pyrylium luminescent material |
| CN108659568A (en) * | 2018-06-19 | 2018-10-16 | 清华大学 | The preparation method of hemicyanine dye and the application in photoacoustic imaging |
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