CN1049232C - Fluorescent dye with double chromogens and preparing process thereof - Google Patents
Fluorescent dye with double chromogens and preparing process thereof Download PDFInfo
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- CN1049232C CN1049232C CN 94113922 CN94113922A CN1049232C CN 1049232 C CN1049232 C CN 1049232C CN 94113922 CN94113922 CN 94113922 CN 94113922 A CN94113922 A CN 94113922A CN 1049232 C CN1049232 C CN 1049232C
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Abstract
The present invention discloses fluorescent dye with double chromogens and a preparation method thereof. A precursor chromogen of a rhodamine compound is grafted with an antenna chromogen which contains at least 1, 8-naphthoylimine derivatives or contains carbazole derivatives, and the fluorescent dye with double chromogens of the present invention is obtained. Therefore, the fluorescence quantum yield is greatly enhanced, and the improvement of the laser technology is impelled.
Description
The present invention relates to a kind of organic dye and synthetic method thereof, particularly a kind of organic fluorescent dye and synthetic method thereof.
The crowd knows known, and rhodamine (Rhodamine) compounds is the higher relatively organic compound of a class fluorescence quantum yield, and this compounds can be at dye laser, and the occasion of its emission visible fluorescence of numerous needs such as fluorescence labelling is used.Weigh the quality of a kind of compound in above-mentioned applications effect, " fluorescence quantum yield " these data are very important index, generally speaking, we require fluorescence quantum yield high more good more, that is to say, we wish that usually the luminous energy of combined thing absorption is converted into the light emission of another wavelength more, rather than with heat energy or other form of energy radiation loss.But general organic fluorescent compounds is because the constitutional features of itself, though higher fluorescence quantum yield is arranged, but its maximum absorption is relative less with radiative wavelength difference (being the Stocks displacement), cause the fluorescent emission energy of this compound self to be absorbed by the ground state compound, for example the rhodamine compounds when it during as the laser dyes in the dye laser, it is in the dye molecule of lowest excited singlet and triplet state, penetrate photon and have self and absorb again swashing, cause the pumping loss, laser radiation efficient is descended greatly, in addition in use, for making fluorescence dye absorb the ultraviolet pump light effectively, usually require to transfer the concentration of dyestuff very high, like this, the power loss of laser radiation is just more serious relatively.For this reason, branch of industry wishes that the scientific worker provides the fluorescence dye of more excellent performance.
Order of the present invention is to overcome the above-mentioned defective that fluorescence dye is arranged, and a kind of fluorescence dye with double-chromophore and preparation method thereof is provided.It has not only been avoided exciting light to be absorbed by the parent of ground state again, and has increased the uptake factor of fluorescence dye in ultraviolet pumping SPECTRAL REGION greatly, and improved fluorescence quantum efficiency effectively with the energy transfer process between two different chromophoric groups.
Design of the present invention is such:
The contriver is on the basis of big quantity research, and the another kind of fluorescent chemicals of imagination grafting on a kind of parent of fluorescent dye compound constitutes a kind of fluorescence dye with double-chromophore.Selection should be had in short wavelength region may by the fluorescent chemicals in the grafting very strong absorption is arranged, but the energy of its emission is not with the luminous energy form but give parent with the form of intramolecular energy transfer with energy transport, cause exciting of parent and emitting fluorescence, thereby increase substantially fluorescence quantum yield.Experimental results show that: 1.24～2.90 times (all being benchmark traditionally) of the fluorescence quantum yield that its fluorescence quantum yield of double-chromophore fluorescence dye of the present invention is a rhodamine B with the rhodamine B.
The present invention also is achieved in that
The contriver is on the basis of being engaged in the fluorescence dye research work for a long time, designed a kind of fluorescence dye that contains the double-chromophore structure, its class in grafting on the parent of rhodamine class fluorescent chromophore contains 1, the derivative of 8 naphthalimide chromophoric groups or a class contain the derivative of carbazole chromophoric group, form the fluorescence dye that a class has double-chromophore, its structure is shown in following formula (1), (2).
1. the parent in the formula (1) is a rhodamine 101, and the parent in the formula (2) is a rhodamine B, and their structural formula is respectively as shown in following:
Rhodamine 101 rhodamine Bs
2.R be another antenna chromophoric group that grafting is got on, it can be 1,8-naphthalimide analog derivative, and its general structure is as the formula (3).
Wherein: R ' can be H, Cl, Br, N (CH
3)
2, OCH
3, OC
2H
5In a kind of; Also can be the carbazoles derivative, its general structure as the formula (4).Wherein: R ' can H, Cl, NH
2, CH
3, a kind of (R ' be positioned at 3-, or on the 4-position) among the OH; N is a methylene bridge chain number, can be one or more, n=1 commonly used, 2,3.In the fluorescence dye of the said double-chromophore of the present invention, contained 1,8 naphthoyl imide compounds or carbazole compound, they are mainly as the antenna chromophoric group, the energy of its absorption can be passed to rhodamine class parent chromophoric group by one or more methylene bridge chain, the chromophoric group that makes the rhodamine compounds excites and sends fluorescence.Because the chromophoric existence of antenna makes compound of the present invention increase greatly in the receptivity of ultraviolet region, then by transmission ofenergy, rhodamine class parent fluorescent quantum emittance is also increased greatly, thereby reach the purpose of Molecular Structure Design of the present invention.
Said its synthetic method of fluorescence dye with double-chromophore of the present invention mainly comprises: the preparation of reaction solution, thermal polycondensation synthesize and the refining three big steps of column chromatography.Wherein:
1. the preparation of reaction solution:
Add rhodamine compounds, solvent, acid binding agent and polymer adjusting control agent in the container together, at room temperature stir half an hour earlier, heated and stirred is warming up to reflux temperature then, till the rhodamine compounds dissolves fully, remove by filter the insoluble impurity of excessive acid binding agent, obtain a transparent solution (abbreviation solution A) with other.
Said rhodamine compounds is mainly rhodamine 101, rhodamine B;
Said solvent can be in acetonitrile, oil of mirbane, the chlorobenzene one or more;
Said acid binding agent is a class alkaline matter, can be in Anhydrous potassium carbonate, anhydrous sodium carbonate, anhydrous potassium hydroxide, the no water sodium hydroxide one or more;
Said polymer adjusting control agent can be in polyoxyethylene glycol, polyvinyl alcohol, the hydroxy alkyl cellulose one or more.
2. thermal polycondensation is synthetic:
In above-mentioned solution A, add 1 of haloalkylation, the carbazoles derivative of 8-naphthalimide analog derivative or adding haloalkylation, under being warming up to reflux temperature, stirring heating reacted 6～10 hours then, at any time follow the tracks of with the thin plate chromatography in the reaction process, the straight spot that ends reaction product no longer changes, and is reaction end.The reaction solution of gained except that after desolvating, promptly gets raw product of the present invention with underpressure distillation.In the building-up process, 1 of haloalkylation, the carbazoles derivative of 8-naphthalimide analog derivative or haloalkylation is suitable excessive, and its consumption is at least rhodamine parent heavy 1.1～1.5 times (mol/mol ratios).
3. column chromatography is refining:
Raw product of the present invention is dissolved in the developping agent,, collects chromatographic solution then by the column chromatography post.After the chromatographic solution evaporation of collecting removed developping agent, obtain a concentrated solution, add the anhydrous diethyl ether precipitation again and separate out product, after filtration, drying, be the said fluorescence dye product of the present invention with double-chromophore.
Said developping agent is the mixed solution that methyl alcohol and methylene dichloride are formed, and its suitable ratio of components is CH
3OH/CH
2Cl
2=0.4/10～0.8/10.
Used column chromatography post is a silicagel column.The consumption of anhydrous diethyl ether is preferably 2～3 times of concentrated solution.
Further illustrate content of the present invention below in conjunction with embodiment, but these embodiment do not limit protection scope of the present invention.
Embodiment 1
With rhodamine B, N-(2-bromotrifluoromethane)-4-dimethylamine-1, the 8-naphthalimide is the synthetic double-chromophore fluorescence dye of the present invention of raw material, wherein:
1. rhodamine B is the commercial goods;
2.N-(2-bromotrifluoromethane)-4-dimethylin-1,8 naphthalimide can be according to Beil.[23, (3), 5588] disclosed technology synthesizes, and its synthetic method is summarized as follows:
(1) 4-dimethylin-1,8-naphthalene acid anhydride synthetic
With 2.4 gram 4-bromo-1,8-naphthalene acid anhydride, the dimethylamine of 0.2 gram cupric sulfate crystals, 6ml33% is water-soluble
Liquid, 40mlDMF join in the 250ml there-necked flask, and under agitation heat temperature raising is to refluxing
Under the temperature, reacted 2 hours, then reaction solution is poured in the 100ml cold water, obtain yellow
Precipitation is filtered then, is washed, drying, is 4-dimethylamine-1,8-naphthalene acid anhydride.This compound
Available ethanol, chlorobenzene difference recrystallization-inferior get orange red acicular crystals.
(2) N-hydroxyethyl-4-dimethylin-1,8-naphthalimide synthetic
In the there-necked flask of 100ml, add 0.22 gram 4-dimethylin-1,8-naphthalene acid anhydride, 2ml thanomin
And 30ml ethanol, under agitation reaction 3.5～4.0 is little down to reflux temperature for heat temperature raising
The time, after etoh solvent is removed in underpressure distillation, pour into and obtain flaky precipitate, mistake then in the water
Filter, washing, drying promptly get N-hydroxyethyl-4-dimethylin-1, the 8-naphthalimide.This change
The further available chlorobenzene recrystallization purifying of compound.
(3) N-(2-bromotrifluoromethane)-4-dimethylin-1,8-naphthalimide synthetic
In the there-necked flask of 100ml, add 1 gram N-hydroxyethyl-4-dimethylin-1,8-naphthoyl Asia
Amine, 60ml exsiccant chlorobenzene are heated to and make its dissolving about 50 ℃, slowly drip with syringe
The dibromo sulfoxide that adds 0.6ml, have yellow solid to separate out in the flask this moment, and then be warming up to
Reaction is 2 hours about 70 ℃, adds 0.3ml dibromo sulfoxide again, and it is little to continue reaction 0.5～1
The time, be warming up to again 90 ℃ the reaction 1 hour, be cooled to room temperature, filter solid, use methyl alcohol
Wash, wash, dry and obtain product, be N-(2-bromotrifluoromethane)-4-dimethylin
-1, the 8-naphthalimide.The further available chlorobenzene recrystallization purifying of this compound.
Because 1,8 naphthalimide derivative of other haloalkylation and the carbazoles of haloalkylation are derived
Thing, because of all can be, (3), 5588 by Beil[23] known technology synthesize, so be omitted.
3. the synthesis step of double-chromophore fluorescence dye is as follows:
(1) preparation of reaction solution:
In the there-necked flask of 100ml, add 0.5 gram rhodamine B, 80ml acetonitrile, the anhydrous carbon of 0.5 gram
Acid potassium, and 0.1 gram polyoxyethylene glycol at room temperature stir half an hour earlier, then heat temperature raising
To reflux temperature, till rhodamine B is dissolved fully.Remove by filter excessive salt of wormwood
And other insoluble impurity, obtain a transparent solution (abbreviation solution A).
(2) thermal polycondensation is synthetic:
In solution A, add 0.44 gram N-(2-bromotrifluoromethane)-4-dimethylin-1,8-naphthoyl Asia
Amine, under agitation heat temperature raising reacted 6～10 hours, in the reaction process to reflux temperature
At any time follow the tracks of with the thin plate chromatography, no longer change, be reaction eventually until the reaction product spot
The point.The gained reaction solution is removed acetonitrile with underpressure distillation, and the reaction product that obtains is the present invention
Raw product.
(3) column chromatography is refining:
With the reaction product raw product of above-mentioned gained, earlier with after a small amount of developping agent dissolving, used exhibition
Opening agent is CH
3OH/CH
2Cl
2=0.4/10～0.8/10, collect chromatographic solution, evaporation removes
Go to obtain a concentrated solution behind the developping agent, with 3 times of anhydrous diethyl ethers to the concentrated solution volume, existing precipitation
Analysed product, after filtration, after the drying, be that the present invention is said to have the glimmering of double-chromophore
One of photoinitiator dye product, its structural formula is as follows:
Through measuring: its quantum yield is 1.5 times of rhodamine B.
Embodiment 2
With rhodamine B, N-(2-bromotrifluoromethane)-4-methoxyl group-1,8 naphthalimide is the synthetic double-chromophore fluorescence dye of the present invention of raw material, and its synthesis step is as follows:
1. the preparation of reaction solution:
In the there-necked flask of 100ml, add 0.5 gram rhodamine B, 80ml oil of mirbane, the anhydrous sodium hydroxide of 0.5 gram, 0.1 gram polyvinyl alcohol at room temperature stirs half an hour earlier, and heated and stirred is warming up to reflux temperature then, till rhodamine B is dissolved fully.Remove by filter excessive sodium hydroxide, obtain a transparent liquid A.
2. thermal polycondensation is synthetic:
In transparent liquid, add 0.46 gram N-(2-bromotrifluoromethane)-4-methoxyl group-1, the 8-naphthalimide, under agitation heat temperature raising was to reflux temperature reaction 8～10 hours, reaction process is followed the tracks of with the thin plate chromatography at any time, no longer change until the reaction product spot, be reaction end, the gained reaction solution is removed oil of mirbane with underpressure distillation, and solid product is raw product of the present invention.
3. column chromatography is refining:
Solid product earlier with after a small amount of developping agent dissolving, is entered the column chromatography post, with developping agent (CH
3OH/CH
2Cl
2=0.4/10～0.8/10) drip washing, product obtains refining the purification at the disconnected post of post layer, collect required chromatographic solution, after developping agent is removed in evaporation, obtain a concentrated solution, with 2 times of anhydrous diethyl ether precipitating products, after filtration, after the drying to the concentrated solution volume, promptly obtain product of the present invention, its structural formula is as follows:
Through measuring: its quantum yield is 2.0 times of rhodamine B.
Embodiment 3
With rhodamine B, N-(2-bromotrifluoromethane)-4-oxyethyl group-1, the 8-naphthalimide is the fluorescence dye of the synthetic double-chromophore of the present invention of raw material, and its synthesis step is as follows:
1. the preparation of reaction solution:
In the 100ml there-necked flask, add 0.5 gram rhodamine B, 80ml chlorobenzene, the anhydrous hydroxide of 0.5 gram
Potassium, 0.1 gram Walocel MT 20.000PV, all the other operation stepss are all with embodiment 1, obtain one transparent
Liquid A.
2. thermal polycondensation is synthetic:
In transparent liquid A, add 0.55 gram N-(2-bromotrifluoromethane)-4-oxyethyl group-1,8-naphthoyl Asia
Amine, all the other operation stepss obtain raw product of the present invention with embodiment 1.
3. column chromatography is refining:
Operating process obtains product of the present invention all with embodiment 1, and its structural formula is:
Through measuring: its quantum yield is 2.0 times of rhodamine B.
Embodiment 4
With rhodamine 101, N-(2-bromotrifluoromethane)-4-dimethylin-1, the 8-naphthalimide is the fluorescence dye of the synthetic double-chromophore of the present invention of raw material, and its synthesis step is as follows:
1. reaction solution preparation:
In the there-necked flask of 100ml, add 0.3 gram rhodamine 101,70ml acetonitrile, 0.30 gram anhydrous K
2CO
3, 0.05 the gram polyoxyethylene glycol, all the other operation stepss obtain a transparent liquid A all with embodiment 1.
2. thermal polycondensation is synthetic:
In transparent liquid A, add 0.25 gram N-(2-bromotrifluoromethane)-4-dimethylin-1, the 8-naphthalimide, all the other operation stepss obtain raw product of the present invention all with embodiment 1.
3. column chromatography is refining:
The working method for the treatment of process obtains product of the present invention all with embodiment 1, and its structural formula is:
Through measuring: its quantum yield is 1.24 times of rhodamine B.
Embodiment 5
With rhodamine 101, N-(2-bromotrifluoromethane)-4-bromo-1, the 8-naphthalimide is synthetic double-colored the fluorescence dye of the present invention of raw material, and its synthesis step is as follows:
1. reaction solution preparation:
In the there-necked flask of 100ml, add 0.30 gram rhodamine 101,80ml acetonitrile, 0.30 anhydrous sodium carbonate, 0.05 gram polyvinyl alcohol, all the other operation stepss obtain a transparent liquid A all with embodiment 1.
2. thermal polycondensation is synthetic:
In transparent liquid A, add 0.30 gram N-(2-bromotrifluoromethane)-4-bromo-1, the 8-naphthalimide, all the other operation stepss obtain raw product of the present invention all with embodiment 1.
3. column chromatography is refining:
The working method for the treatment of process obtains product of the present invention all with embodiment 1, and its structural formula is:
Through measuring: its quantum yield is 2.9 times of rhodamine B.
Embodiment 6
With rhodamine 101, N-(2-bromotrifluoromethane)-4-hydroxycarbazole is the synthetic double-chromophore fluorescence dye of the present invention of raw material, and its synthesis step is as follows:
1. reaction solution preparation:
In the there-necked flask of 100ml, add 0.30 gram rhodamine 101,80ml acetonitrile, 0.30 gram Anhydrous potassium carbonate, 0.05 gram polyoxyethylene glycol, all the other operation stepss obtain a transparent liquid A all with embodiment 1.
2. thermal polycondensation is synthetic:
Add 0.21 gram N-(2-bromotrifluoromethane)-4-hydroxycarbazole in transparent liquid A, all the other operation stepss obtain raw product of the present invention all with embodiment 1.
3. column chromatography is refining:
The method for the treatment of process obtains product of the present invention all with embodiment 1, and its structural formula is:
Through measuring: its quantum yield is 1.8 times of rhodamine B.
Obviously, according to design of the present invention and said synthetic method, chemist in arbitrary the professional domain all can synthesize the fluorescence dye with double-chromophore that obtains other kind of being showed as structural formula (1) or (2) easily.If as being used for industrial production, application, sale and import and being used for above-mentioned purpose, must constitute infringement like this to right of the present invention.
Claims (2)
1. fluorescence dye with double-chromophore is characterized in that:
The fluorescence dye of said double-chromophore is that a class has the compound shown in following general structure (1) or (2):
Wherein:
(1) parent in the formula (1) is a rhodamine 101, and parent is a rhodamine B in the formula (2);
(2) R is another antenna chromophoric group that grafting is got on, and it is 1, the 8-naphthalimide derivative,
Its structural formula is as the formula (3):
Wherein R is H, Cl, Br, N (CH
3)
2, OCH
3, OC
2H
5In a kind of;
Or R is the carbazoles derivative, shown in structural formula (4):
Wherein R ' is H, Cl, NH
2, CH
3, a kind of among the OH;
(3) n is a methylene bridge chain number, n=1 commonly used, 2,3.
2. the fluorescence dye of double-chromophore as claimed in claim 1, its preparation method is characterised in that:
Said preparation method mainly comprises the preparation of reaction solution, the synthetic and refining three big steps of column chromatography of thermal polycondensation, wherein:
(1) reaction solution preparation:
To contain chromophoric rhodamine compounds of parent and solvent, acid binding agent and polymer adjusting control agent heated and stirred and be warming up to reflux temperature, and till the rhodamine compounds dissolves fully, filter and obtain a transparent liquid A;
Said rhodamine compounds is rhodamine 101 or rhodamine B;
Said solvent is one or more in acetonitrile, oil of mirbane or the chlorobenzene;
Said acid binding agent is Anhydrous potassium carbonate, anhydrous sodium carbonate, anhydrous potassium hydroxide or does not have in the water sodium hydroxide one or more;
Said polymer adjusting control agent is one or more in polyoxyethylene glycol, polyvinyl alcohol, the hydroxy alkyl cellulose;
(2) pyrocondensation is synthetic:
In the solution A that contains rhodamine class parent compound, add 1 of haloalkylation, the carbazoles derivative of 8-naphthalimide derivative or haloalkylation, heated and stirred is warming up to reflux temperature then, reacted 6～10 hours, the gained reaction solution except that after desolvating, promptly obtains raw product of the present invention with underpressure distillation;
(3) column chromatography is refining:
Raw product is dissolved in the developping agent,, collects the chromatographic solution evaporation and remove and add the anhydrous diethyl ether precipitation again behind the developping agent and separate out product, after filtration, drying, be fluorescence dye with double-chromophore then by the column chromatography post;
Said developping agent is the mixture that methyl alcohol and methylene dichloride are formed, and its ratio is:
CH
3OH/CH
2Cl
2＝0.4/10～0.8/10。
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|---|---|---|---|
| CN 94113922 CN1049232C (en) | 1994-09-29 | 1994-09-29 | Fluorescent dye with double chromogens and preparing process thereof |
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|---|---|---|---|
| CN 94113922 CN1049232C (en) | 1994-09-29 | 1994-09-29 | Fluorescent dye with double chromogens and preparing process thereof |
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|---|---|
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| CN1049232C true CN1049232C (en) | 2000-02-09 |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1317334C (en) * | 2004-05-20 | 2007-05-23 | 中国科学院化学研究所 | Intermolecular charge transfer type fluorescent dyes and use thereof |
| US8440835B2 (en) | 2007-02-26 | 2013-05-14 | Massachusetts Institute Of Technology | Environmentally sensitive fluorophores |
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| CN100360932C (en) * | 2005-09-16 | 2008-01-09 | 厦门大学 | Reagent for detecting mercury ion in water and its preparation method |
| CN101135644B (en) * | 2007-08-16 | 2010-05-19 | 南京大学 | Mercury ion fluorescent color-developing agent and detecting method |
| CN102304295A (en) * | 2011-07-12 | 2012-01-04 | 核工业理化工程研究院 | Preparation method of rhodamine 101 ester laser dye suitable for 532nm laser pumping |
| CN102627636B (en) * | 2012-03-31 | 2014-07-30 | 天津师范大学 | Preparation method for naphthyl substituted rhodamine B oxadiazole compound and application thereof |
| CN102627637B (en) * | 2012-03-31 | 2014-07-16 | 天津师范大学 | Preparation method and application of substituted phenyl rhodamine oxadiazole compounds |
| CN102633788B (en) * | 2012-03-31 | 2014-07-16 | 天津师范大学 | P-methylphenyl rhodamine oxadiazole as well as preparation method and application thereof |
| CN104710816B (en) * | 2013-12-17 | 2017-05-10 | 中国科学院大连化学物理研究所 | Large Stokes shift and near infrared fluorescence emitting new rhodamine fluorescent dye and synthetic method thereof |
| CN104710815B (en) * | 2013-12-17 | 2017-05-10 | 中国科学院大连化学物理研究所 | Novel rhodafluor fluorescent dye with characteristics of large stokes shift and near-infrared fluorescence emitting, and synthesis method thereof |
| CN108516979B (en) * | 2018-05-18 | 2020-08-25 | 华东理工大学 | Compound based on naphthalimide-rhodamine and application thereof |
-
1994
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1317334C (en) * | 2004-05-20 | 2007-05-23 | 中国科学院化学研究所 | Intermolecular charge transfer type fluorescent dyes and use thereof |
| US8440835B2 (en) | 2007-02-26 | 2013-05-14 | Massachusetts Institute Of Technology | Environmentally sensitive fluorophores |
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| Publication number | Publication date |
|---|---|
| CN1101929A (en) | 1995-04-26 |
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