CN109734736A - Seven yuan of fluorine boron fluorescent dyes of one kind and its synthetic method - Google Patents
Seven yuan of fluorine boron fluorescent dyes of one kind and its synthetic method Download PDFInfo
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Abstract
It is as follows containing the novel seven yuan of fluorine boron fluorescent dyes of electron donor/electron acceptor and its synthetic method, the compound structure that the invention discloses a kind of:Wherein, substituent R is the electron-withdrawing groups such as electron-donating groups and acyl group, aldehyde radical, carboxyl, acylamino-, sulfonic group, itrile group, nitro, haloform base, quaternary amine base such as alkoxy, amino, hydroxyl.With 2,3,3- tri-methyl indole derivatives and 2- formylpyrrole for raw material, through Knoevenagel condensation reaction under organic catalyst effect, seven yuan of fluorine boron fluorescent dyes of supplied for electronic/electrophilic are ultimately produced.Such contains that seven yuan of fluorine boron fluorescent dye synthetic methods of electron donor/electron acceptor are simple, and reaction condition is easily controllable, has universal applicability.The material can be by selecting suitable fluorogen, electron donor and electron acceptor is pi-conjugated to its, band gap and photoelectric property are effectively regulated and controled.
Description
Technical field
The invention discloses a kind of simultaneously comprising seven yuan of fluorine boron fluorescent dyes of electron donor/electron acceptor and its synthesis side
Method, such dyestuff can be widely used in the fields such as environment, analysis, material science.
Background technique
In extensive organic π system, electron donor/electron acceptor type organic compound has since band gap is lower
Various excellent photoelectric properties, the interest for having caused people increasing in recent years.Another is attractive for this kind of material
Advantage is exactly can be by selecting suitable fluorogen, electron donor and electron acceptor is pi-conjugated to its, band gap and photoelectric property
Effectively regulated and controled.Fluorine boron fluorochrome (BODIPY) with preferable stability, modifiability, high mole due to disappearing
Backscatter extinction logarithmic ratio and preferable oxidizing potential have the group of corresponding function can in its modifiable position by the access of selectivity
Since adjust the physical properties such as optical properties, stability and chemical property and dissolubility such as absorbing wavelength of BODIPY dye.
Up to the present, the BODIPY dyestuff of electron donor and electron acceptor has been developed that and applies in every field.
However, up to the present, relatively common electron donor and electron acceptor BODIPY dyestuff its emit cluster centre and be
Hexatomic ring, report and few, abundant design and the optimization of rational routes of the shortage to molecule to heptatomic ring, and also there are structures
Therefore single problem prepares the fluorine boron dye at novel heptatomic ring center from raw material by simple synthetic route
Material is problem urgently to be resolved.
Present invention design synthesized a series of structure novels based on containing electron donor/electron acceptor seven yuan of fluorine boron dye
Material, is optimized the synthetic method of this kind of compound, improves its synthetic yield, by the optical physics for studying such compound
Property discloses the relationship between this kind of molecular structure and property.
Summary of the invention
The main purpose of the present invention is to provide a kind of seven yuan of fluorine boron fluorescent dyes of electron donor/electron acceptor and its synthesis
Method.
Technical scheme is as follows:
A kind of seven yuan of fluorine boron fluorescent dyes of electron donor/electron acceptor, the chemical structural formula of the compound are as follows:
Wherein, substituent R be electron-donating group or electron-withdrawing group, the electron-donating group include alkoxy, amino,
Any one in hydroxyl；The electron-withdrawing group include acyl group, aldehyde radical, carboxyl, acylamino-, sulfonic group, itrile group, nitro,
Any one in haloform base, quaternary amine base.
Dyestuff chemistry structural formula described in further preferred scheme are as follows:
In any one.
The synthetic method of synthesis seven yuan of fluorine boron fluorescent dyes of electron donor/electron acceptor, the method includes with
Lower synthesis path:
It the described method comprises the following steps:
(1) into reaction flask, addition compound 1, ethyl alcohol, compound 2, temperature rising reflux obtain solid chemical combination at room temperature
Object；
(2) it purifies the solid chemical compound in the step (1) to obtain yellow solid compound 3；
(3) toluene is added in the compound 3 in step (2) respectively, and boron trifluoride ether complexing is slowly added dropwise in triethylamine
Object is warming up to 100-130 DEG C and is stirred at reflux, obtains reaction solution；
(4) reaction solution in step (3) washed respectively, extracted, is dry, purified after concentration, obtain product 3B, i.e. electronics
Seven yuan of fluorine boron fluorescent dyes of donor/electron acceptor.
The feed ratio of compound 1 and compound 2 is 1: 1-100 in the step (1).Change feed ratio, the receipts of compound 3
Rate improves a lot.
Compound 1 need to use the salt after protonation in the step (1), and otherwise, reaction does not occur or yield is very low.
The sequence that the step (1) feeds intake is compound 1, compound 2, ethyl alcohol.If other charging sequences can make instead
It answers system heating acutely, is not easy to the expansion of reaction substrate.
Step (1) counterflow condition is to be warming up to 80-90 DEG C, is flowed back 2-18 hours.Reach reflux temperature, reacts ability
It goes on smoothly, otherwise reacts insufficient, yield is low, and the reaction time is long.
Compound 3 and the feed ratio of boron trifluoride ether are 1: 1-100 in the step (3).Change feed ratio, product
Yield can improve a lot, and the range of feed ratio is larger, be conducive to the production of fine chemicals.
The sequence that the step (3) feeds intake is compound 3, toluene, triethylamine, boron trifluoride ether.This feeding sequence, makes
Reaction can be gone on smoothly, and boron trifluoride ether need to be eventually adding.
Step (3) the heating reaction temperature is 120 DEG C, reaction time 0.5-8h.This reflux temperature can make reaction just
Often carry out.According to the difference of substrate, the reaction time is indefinite.
The present invention has the beneficial effect that:
(1) Knoevenagel contracting is carried out with formylpyrrole by the raw material with electron-donating group or drawing electron group
Reaction is closed, important intermediate 3 has been synthesized, has then obtained final product after fluoroboration.This kind of dyestuff is with seven yuan of fluorine boron complexs
Centered on, supplied for electronic is introduced in the side of entire molecule or drawing electron group increases the conjugacy of molecule, is conducive to intramolecular
Charge transmission, so that it is had good Photophysics.
(2) synthetic reaction condition of the invention is easily controllable, and product purification is relatively simple, has universal applicability.
(3) synthesis step of the invention is simple, and reaction condition is mild.
(4) the compound of the present invention fluorescence quantum yield is high, and Stokes shift is big, can apply in fluorescence imaging.
Detailed description of the invention
Fig. 1 is the fluorescence spectra of the obtained product of embodiment 8.
Fig. 2 is the fluorescence spectra of the obtained product of embodiment 11.
Fig. 3 is the fluorescence spectra of the obtained product of embodiment 10.
Fig. 4 is the fluorescence spectra of the obtained product of embodiment 7.
Fig. 5 is the fluorescence spectra of the obtained product of embodiment 9.
Fig. 6 is the hydrogen spectrum of the obtained product of embodiment 1-7.
Fig. 7 is the carbon spectrum of the obtained product of embodiment 1-7.
Fig. 8 is the mass spectrum of the obtained product of embodiment 1-7.
Specific embodiment
The present invention is further illustrated below with reference to embodiment, but the scope of protection of present invention is not limited to implement
The range of example statement.
Embodiment 1
2,3,3- trimethyl -5- methoxy-Indole protonated salts 1 (1.71g, 9.00mmol) are taken, 2- formylpyrrole is weighed
(1.72g, 18.00mmol), measures ethanol solution 0.15L, and heating stirring after mixed dissolution flows back 4 hours in 90 DEG C, is spin-dried for
Purification by filtration obtains the compound 3 of yellow afterwards, takes above compound 3 (133.2mg, 0.5mmol), takes 35.00ml toluene solution,
1.00ml triethylamine, under electromagnetic agitation, slowly be added dropwise boron trifluoride ether solution (1.00ml), increase temperature to 120 DEG C,
Flow back 30min, and product is washed, extracted by the detection of TLC contact plate, and dry, revolving, Purification by filtration obtains final products, specific to tie
Structure formula is as follows:
Embodiment 2
2,3,3- trimethyl -5- methoxy-Indole protonated salts 1 (3.42g, 18.00mmol) are taken, 2- formylpyrrole is weighed
(1.72g, 18.00mmol), measures ethanol solution 0.15L, and heating stirring after mixed dissolution flows back 2 hours in 90 DEG C, after being spin-dried for
Purification by filtration obtains the compound 3 of yellow, takes above compound 3 (133.2mg, 0.5mmol), takes 35.00ml toluene solution,
Boron trifluoride ether solution (1.00ml) slowly is added dropwise under electromagnetic agitation in 1.00ml triethylamine, increases temperature to 120 DEG C, returns
30min is flowed, product is washed, extracted by the detection of TLC contact plate, and dry, revolving, Purification by filtration obtains final products, concrete structure formula
It is as follows:
Embodiment 3
2,3,3- trimethyl -5- methoxy-Indole protonated salts 1 (1.71g, 9.00mmol) are taken, 2- formylpyrrole is weighed
(1.72g, 18.00mmol), measures ethanol solution 0.15L, and heating stirring after mixed dissolution flows back 2 hours in 90 DEG C, after being spin-dried for
Purification by filtration obtains the compound 3 of yellow, removes above compound 3 (133.2mg, 0.5mmol) respectively, takes 35.00ml toluene molten
Boron trifluoride ether solution (1.00ml) slowly is added dropwise under electromagnetic agitation in liquid, 1.00ml triethylamine, increases temperature to 1 20
DEG C, flow back 30min, and product is washed, extracted by the detection of TLC contact plate, and dry, revolving, Purification by filtration obtains final products, specifically
Structural formula is as follows:
Embodiment 4
2,3,3- trimethyl -5- methoxy-Indole protonated salts 1 (1.71g, 9.00mmol) are taken, 2- formylpyrrole is weighed
(855.9mg, 9.00mmol), measures ethanol solution 0.15L, and heating stirring after mixed dissolution flows back 2 hours in 90 DEG C, is spin-dried for
Purification by filtration obtains the compound 3 of yellow afterwards, takes above compound 3 (133.2mg, 0.5mmol), takes 35.00ml toluene molten
Boron trifluoride ether solution (10.00ml) slowly is added dropwise under electromagnetic agitation in liquid, 1.00ml triethylamine, increases temperature to 120
DEG C, flow back 30min, and product is washed, extracted by the detection of TLC contact plate, and dry, revolving, Purification by filtration obtains final products, specifically
Structural formula is as follows:
Embodiment 5
2,3,3- trimethyl -5- methoxy-Indole protonated salts 1 (1.71g, 9.00mmol) are taken, 2- formylpyrrole is weighed
(855.9mg, 9.00mmol), measures ethanol solution 0.15L, and heating stirring after mixed dissolution flows back 2 hours in 90 DEG C, is spin-dried for
Purification by filtration obtains the compound 3 of yellow afterwards, takes above compound 3 (133.2mg, 0.5mmol) respectively, takes 35.00ml toluene
Solution, 1.00ml triethylamine are slowly added dropwise boron trifluoride ether solution (50.00ml) under electromagnetic agitation, increase temperature extremely
120 DEG C, flow back 30min, and product is washed, extracted by the detection of TLC contact plate, and dry, revolving, Purification by filtration obtains final products, has
Body structural formula is as follows:
Embodiment 6
2,3,3- trimethyl -5- methoxy-Indole protonated salts 1 (1.71g, 9.00mmol) are taken, 2- formylpyrrole is weighed
(855.9mg, 9.00mmol), measures ethanol solution 0.15L, and heating stirring after mixed dissolution flows back 2 hours in 90 DEG C, is spin-dried for
Purification by filtration obtains the compound 3 of yellow afterwards, removes above compound 3 (133.2mg, 0.5mmol) respectively, takes 35.00ml toluene
Solution, 5.00ml triethylamine are slowly added dropwise boron trifluoride ether solution (100.00m1) under electromagnetic agitation, increase temperature extremely
120 DEG C, flow back 30min, and product is washed, extracted by the detection of TLC contact plate, and dry, revolving, Purification by filtration obtains final products, has
Body structural formula is as follows:
Embodiment 7
2,3,3- trimethyl -5- methoxy-Indole protonated salts 1 (1.71g, 9.00mmol) are taken, 2- formylpyrrole is weighed
(855.9mg, 9.00mmol), measures ethanol solution 0.15L, and heating stirring after mixed dissolution flows back 2 hours in 90 DEG C, is spin-dried for
Purification by filtration obtains the compound 3 of yellow afterwards, removes above compound 3 (133.2mg, 0.5mmol) respectively, takes 35.00ml toluene
Boron trifluoride ether solution (1.00m1) slowly is added dropwise under electromagnetic agitation in solution, 5.00ml triethylamine, increases temperature to 1
20 DEG C, flow back 30min, and product is washed, extracted by the detection of TLC contact plate, and dry, revolving, Purification by filtration obtains final products, has
Body structural formula is as follows:
Embodiment 8
Take 2,3,3- tri-methyl indole protonated salts 1 (1.71g, 9.00mmol), 2- formylpyrrole (855.9mg,
9.00mmol) and ethanol solution 0.15L, heating stirring after mixed dissolution, flows back 2 hours in 90 DEG C, is spin-dried for rear Purification by filtration and obtains
To the compound 3 of yellow, above compound 3 (0.5mmol) is taken respectively, takes 35.00ml toluene solution, 5.00ml triethylamine,
Under electromagnetic agitation, boron trifluoride ether solution (1.00ml) slowly is added dropwise, increases temperature to 120 DEG C, flow back 30min, TLC contact plate
Detection, product is washed, and is extracted, dry, and revolving, Purification by filtration obtains final products, and concrete structure formula is as follows:
Embodiment 9
Take 2,3,3- trimethyl -5- ethoxycarbonyl indoles protonated salt 1 (1.71g, 9.00mmol), 2- formylpyrrole
(855.9mg, 9.00mmol) and ethanol solution 0.15L, heating stirring after mixed dissolution flow back 2 hours in 90 DEG C, after being spin-dried for
Purification by filtration obtains the compound 3 of yellow, takes above compound 3 (0.5 mmol) respectively, takes 35.00ml toluene solution,
Boron trifluoride ether solution (1.00ml) slowly is added dropwise under electromagnetic agitation in 5.00ml triethylamine, increases temperature to 120 DEG C, returns
30min is flowed, product is washed, extracted by the detection of TLC contact plate, and dry, revolving, Purification by filtration obtains final products, concrete structure formula
It is as follows:
Embodiment 10
Take 2,3,3- trimethyl -5- bromo indole protonated salts 1 (1.71g, 9.00mmol), 2- formylpyrrole (855.9mg,
9.00mmol) and ethanol solution 0.15L, heating stirring after mixed dissolution, flows back 2 hours in 90 DEG C, is spin-dried for rear Purification by filtration and obtains
To the compound 3 of yellow, above compound 3 (0.5mm0l) is taken respectively, takes 35.00ml toluene solution, 5.00ml triethylamine,
Under electromagnetic agitation, boron trifluoride ether solution (1.00ml) slowly is added dropwise, increases temperature to 120 DEG C, flow back 30min, TLC point
Plate detection, product is washed, and is extracted, dry, and revolving, Purification by filtration obtains final products, and concrete structure formula is as follows:
Embodiment 11
Take 2,3,3- trimethyl -5- chloro-indole protonated salts 1 (1.71g, 9.00mmol), 2- formylpyrrole (855.9mg,
9.00mmol) and ethanol solution 0.15L, heating stirring after mixed dissolution, flows back 2 hours in 90 DEG C, is spin-dried for rear Purification by filtration and obtains
To the compound 3 of yellow, above compound 3 (133.2mg, 0.5mmol) is taken respectively, takes 35.00ml toluene solution, 5.00ml
Boron trifluoride ether solution (1.00ml) slowly is added dropwise under electromagnetic agitation in triethylamine, increases temperature to 1 20 DEG C, flows back
The detection of 30min, TLC contact plate, product is washed, and is extracted, dry, and revolving, Purification by filtration obtains final products, and concrete structure formula is such as
Under:
The above embodiments are only the preferred technical solution of the present invention, and are not construed as limitation of the invention, this Shen
Please in embodiment and embodiment in feature in the absence of conflict, can mutual any combination.Protection model of the invention
The technical solution that should be recorded with claim is enclosed, the equivalent replacement side of technical characteristic in the technical solution recorded including claim
Case is protection scope.Equivalent replacement i.e. within this range is improved, also within protection scope of the present invention.
Above-described embodiment can be applied obviously in fluorescence luminescent material, and luminous efficiency is high, glimmering in toluene solution
Photo-quantum efficiency is 0.22-0.49, it is shown that its application performance in biology and luminescent material.
Claims (10)
1. a kind of seven yuan of fluorine boron fluorescent dyes of electron donor/electron acceptor, which is characterized in that the dyestuff chemistry structural formula are as follows:
Wherein, substituent R is electron-donating group or electron-withdrawing group, and the electron-donating group includes alkoxy, amino, hydroxyl
In any one；The electron-withdrawing group includes acyl group, aldehyde radical, carboxyl, acylamino-, sulfonic group, itrile group, nitro, haloform
Any one in base, quaternary amine base.
2. seven yuan of fluorine boron fluorescent dyes of electron donor/electron acceptor according to claim 1, which is characterized in that the dye
Expect chemical structural formula are as follows:
In any one.
3. the synthetic method of seven yuan of fluorine boron fluorescent dyes of electron donor/electron acceptor according to claim 1 or 2, special
Sign is that the method includes following synthesis paths:
(1) into reaction flask, addition compound 1, ethyl alcohol, compound 2, temperature rising reflux obtain solid chemical compound at room temperature；
(2) it purifies the solid chemical compound in the step (1) to obtain yellow solid compound 3；
(3) toluene is added in the compound 3 in step (2) respectively, and boron trifluoride etherate is slowly added dropwise in triethylamine,
It is warming up to 100-130 DEG C to be stirred at reflux, obtains reaction solution；
(4) reaction solution in step (3) washed respectively, extracted, is dry, purified after concentration, obtain product 3B, is i.e. electronics is given
Seven yuan of fluorine boron fluorescent dyes of body/electron acceptor.
4. the synthetic method of seven yuan of fluorine boron fluorescent dyes of electron donor/electron acceptor according to claim 3, feature exist
In in the step (1), compound 1 is 2,3,3- tri-methyl indole derivatives after proton activation, and the compound 2 is
2- formylpyrrole；The feed ratio of compound 1 and compound 2 is 1:1-100.
5. the synthetic method of seven yuan of fluorine boron fluorescent dyes of electron donor/electron acceptor according to claim 3, feature exist
In the feeding sequence of the step (1) is compound 1, compound 2, ethyl alcohol.
6. the synthetic method of seven yuan of fluorine boron fluorescent dyes of electron donor/electron acceptor according to claim 3, feature exist
In the reflux temperature of the step (1) is 80-90 DEG C, and return time is 2-18 hours.
7. the synthetic method of seven yuan of fluorine boron fluorescent dyes of electron donor/electron acceptor according to claim 3, feature exist
In the compound 3 of the step (3) and the mass ratio that feeds intake of boron trifluoride etherate are 1:1-100.
8. the synthetic method of seven yuan of fluorine boron fluorescent dyes of electron donor/electron acceptor according to claim 3, feature exist
In in the step (3), for toluene as solvent, the molar ratio of triethylamine and boron trifluoride ether is 1:1-25.
9. the synthetic method of seven yuan of fluorine boron fluorescent dyes of electron donor/electron acceptor according to claim 3, feature exist
In in the step (3), the sequence to feed intake is compound 3, toluene, triethylamine, boron trifluoride ether.
10. the synthetic method of seven yuan of fluorine boron fluorescent dyes of electron donor/electron acceptor according to claim 3, feature
It is, in the step (3), heating reaction temperature is 120 DEG C, reflux time 0.5-8h.
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| CN109916866A (en) * | 2019-03-04 | 2019-06-21 | 三峡大学 | A kind of new application of seven yuan of fluorine boron fluorescent dye |
| CN111100476A (en) * | 2019-12-05 | 2020-05-05 | 三峡大学 | Synthesis and application of pH fluorescent probe |
| CN111349109A (en) * | 2020-04-02 | 2020-06-30 | 三峡大学 | Synthetic method of seven-element boron dipyrromethene fluorescent dye |
| CN112442059A (en) * | 2020-12-10 | 2021-03-05 | 青海大学 | Seven-membered ring N, N-chelate boron complex, preparation method thereof, luminescent material and luminescent device |
| CN113105487A (en) * | 2021-03-17 | 2021-07-13 | 三峡大学 | Seven-element boron fluoride fluorescent dye and application thereof in fluorescent anti-counterfeiting film |
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| CN109916866A (en) * | 2019-03-04 | 2019-06-21 | 三峡大学 | A kind of new application of seven yuan of fluorine boron fluorescent dye |
| CN109916866B (en) * | 2019-03-04 | 2021-06-29 | 三峡大学 | New application of seven-element boron fluoride fluorescent dye |
| CN111100476A (en) * | 2019-12-05 | 2020-05-05 | 三峡大学 | Synthesis and application of pH fluorescent probe |
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| CN111349109A (en) * | 2020-04-02 | 2020-06-30 | 三峡大学 | Synthetic method of seven-element boron dipyrromethene fluorescent dye |
| CN112442059A (en) * | 2020-12-10 | 2021-03-05 | 青海大学 | Seven-membered ring N, N-chelate boron complex, preparation method thereof, luminescent material and luminescent device |
| CN112442059B (en) * | 2020-12-10 | 2021-09-07 | 青海大学 | Seven-membered ring N, N-chelate boron complex, preparation method thereof, luminescent material and luminescent device |
| CN113105487A (en) * | 2021-03-17 | 2021-07-13 | 三峡大学 | Seven-element boron fluoride fluorescent dye and application thereof in fluorescent anti-counterfeiting film |
| CN113105488A (en) * | 2021-03-17 | 2021-07-13 | 三峡大学 | Synthesis method and application of viscosity-responsive conjugated BOPYIN fluorescent dye |
| CN113105488B (en) * | 2021-03-17 | 2023-10-27 | 三峡大学 | Synthesis method and application of conjugated BOPYAIN fluorescent dye responding to viscosity |
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