CN106632203A - Dicyanomethylenebenzotetrahydrofuran derivative and preparation method thereof - Google Patents
Dicyanomethylenebenzotetrahydrofuran derivative and preparation method thereof Download PDFInfo
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Abstract
The invention provides a dicyanomethylenebenzotetrahydrofuran derivative and a preparation method thereof. A classic dicyanomethylenebenzotetrahydrofuran derivative containing hydroxyl (hereinafter referred to as DCM-OH) is used as a raw material, and one hydrogen bond receptor formyl is introduced to a hydroxyl ortho-position to obtain the dicyanomethylenebenzotetrahydrofuran derivative with an intramolecular hydrogen bond effect (hereinafter referred to as DCM-OH-CHO). Compared with traditional DCM-OH, the DCM-OH-CHO prepared by the method has the characteristics of higher quantum yield and relatively high fluorescence stability and is more suitable for being modified again and the like.
Description
Technical field
The invention belongs to organic functional material preparing technical field, is related to a kind of dicyano methene benzo tetrahydrofuran and spreads out
Biology and preparation method thereof.
Background technology
In recent years, dicyano methene benzo tetrahydrofuran derivatives are because of its excellent photoelectric properties, red fluorescence transmitting
With favored by numerous researchers the advantages of good photostability.This kind of organic compound is usually used in fluorescent molecular probe,
The fields such as Molecular Logic Gates, light sensitizer and Organic Light Emitting Diode.But due to there is intermolecular aggregation quenching phenomenon, mostly
Number dicyano methene benzo tetrahydrofuran derivatives fluorescence quantum yield is low, therefore greatly limit extensively should for this kind of material
With.The method of the dicyano methene benzo tetrahydrofuran derivatives quantum rate of report raising at present is broadly divided into and " introduces dendritic base
Group " and " introducing higher supplied for electronic and/or drawing electron group ".On dicyano methene benzo tetrahydrofuran derivatives skeleton
Introducing the larger group of steric hindrance can reduce intermolecular π-π * accumulations so as to strengthen fluorescence quantum yield.But due to dendrimeric group
Space steric effect and substituent effect so that the modification again of this kind of material becomes more difficult, therefore limits dicyan
Methylmethyiene base benzo tetrahydrofuran derivatives synthesize and deeper application.The higher confession of introducing and/or drawing electron group can increase
Push-pull effect in strong dicyano methene benzo tetrahydrofuran derivatives, so as to strengthen fluorescence quantum yield.But, utilize this
Compound maximum fluorescence emission blue shift prepared by the method for kind, positioned at red light region (λem≤ 650nm) outside.Additionally, the confession for introducing
And/or drawing electron group has occupied the avtive spot of these compounds so that introducing other functional groups becomes more difficult.
For problem above, therefore develop a kind of simple, effective method reduction intermolecular aggregation quenching effect raising two
The fluorescence quantum yield of cyano group methene benzo tetrahydrofuran derivatives has very important significance.
The content of the invention
Method for preparing high-fluorescence quantum yield dicyano methene benzo tetrahydrofuran derivatives at present exists glimmering
The problems such as quantum yield is low, synthesis is complicated, stability is poor, again modification is difficult, the invention provides a kind of dicyan methylmethyiene
Base benzo tetrahydrofuran derivatives and preparation method thereof, this method is with the classical dicyano methene benzo four comprising hydroxyl
Hydrogen furan derivatives (abbreviation DCM-OH) are raw material, introduce a hydrogen bond receptor aldehyde radical i.e. available one at hydroxyl ortho position and have
Dicyano methene benzo tetrahydrofuran derivatives (abbreviation DCM-OH-CHO) of intramolecular hydrogen bond effect.With traditional DCM-OH
Compare, DCM-OH-CHO prepared by the method has higher quantum yield, stronger fluorescent stability is more suitable for modifying again
The features such as.
For achieving the above object, the technical scheme is that：
A kind of dicyano methene benzo tetrahydrofuran derivatives, molecular formula is：
(abbreviation DCM-OH-CHO).
The preparation method of the dicyano methene benzo tetrahydrofuran derivatives, comprises the following steps：
(1) with DCM-OH as raw material, hexamethylenetetramine and acid are added, is well mixed, obtain mixed liquor；The mixed liquor is matched somebody with somebody
Square ratio is：
270 milligrams of DCM-OH (0.8 mM)
Hexamethylenetetramine 56-1120 milligrams (0.4-8 mM)
The volume 8-20 milliliter of acid；
The molecular formula of wherein described DCM-OH is：
One or more of the acid in hydrochloric acid, acetic acid and trifluoroacetic acid；
(2) by above-mentioned mixed-liquor return 1-10 hours；
(3) after reaction terminates, it is cooled to room temperature；Neutralization remaining acid solution, extracts organic substance, is dried organic phase, and decompression is steamed
Solvent is removed in distillation, obtains crude product；
(4) target product is obtained after the crude product purified by silica gel chromatographic purification.
Preferred version, step (1) the mixture formula ratio is：
270 milligrams of DCM-OH (0.8 mM)
Hexamethylenetetramine (HMT) 224-896 milligrams (1.6-6.4 mM)
The volume 8-20 milliliter of acid.
Further preferably, step (1) the mixture formula ratio is：
270 milligrams of DCM-OH (0.8 mM)
Hexamethylenetetramine (HMT) 224-560 milligrams (1.6-4.0 mM)
The volume 8-20 milliliter of acid.
Preferred version, step (1) acid is trifluoroacetic acid.
Preferred version, step (2) is to react 5 hours to 10 hours under reflux.
Preferred version, step (3) is to adopt in saturated sodium bicarbonate solution and unnecessary acid solution, is extracted with dichloromethane organic
Compound.
Preferred version, step (4) separating-purifying is as eluant, eluent using dichloromethane.
The crude product is the dicyano methene benzo tetrahydrofuran derivatives containing one and/or two aldehyde radical；It is described
"and/or" means the one kind or two in the dicyano methene benzo tetrahydrofuran derivatives containing one and two aldehyde radical
Kind.
In the present invention, dicyano methene benzo tetrahydrofuran derivatives (DCM-OH) are modification object, so
There must be DCM-OH in reaction raw materials.The DCM-OH for being used is synthesized according to literature procedure, its structure Jing nuclear magnetic resonance
Characterize and confirm.
The preparation method of the present invention receives feed proportioning ratio, reaction time and sour consumption to affect big.Feed proportioning than excessive,
Reaction time is long all to produce the accessory substance containing two aldehyde radicals, separate product difficult；Feed proportioning is than too low, the reaction time
It is too short to cause the yield of DCM-OH-CHO to reduce.The species and consumption of acid is also very crucial, and suitable acid can shorten the reaction time,
Improve reaction yield；Suitable consumption can avoid wastage of material.
In the present invention, hexa consumption and reaction time are crucial, by controlling hexa consumption
It is capable of achieving to efficiently synthesize DCM-OH-CHO with the reaction time.When hexa consumption is 56 milligrams to 224 milligrams
When, the yield of DCM-OH-CHO is relatively low；When the control of hexa consumption is between 224 milligrams to 896 milligrams, produce
Thing DCM-OH-CHO is of a relatively high, the product yield high most preferably between 224 milligrams to 560 milligrams；When hexa is used
After amount is more than 896 milligrams, DCM-OH-CHO is spread out by aldehyde radical metaplasia into the dicyano methene benzo tetrahydrofuran containing two aldehyde radicals
Biology, yield is reduced.Control in 1 hour to 5 hours, have DCM-OH-CHO to generate between when reacted, but also have part former
Material unreacted is complete；When the time is in 5 hours to 10 hours, DCM-OH has reacted complete；After reaction time was more than 10 hours, part
By aldehyde radical metaplasia into the dicyano methene benzo tetrahydrofuran derivatives containing two aldehyde radicals, yield is reduced DCM-OH-CHO.
Compared with prior art, innovation of the invention is：
1st, the present invention successfully synthesizes a kind of new dicyano methene benzo tetrahydrofuran derivatives, with stronger glimmering
Photostability, is more suitable for modifying again.
2nd, the method for the present invention compares the sterically hindered larger group of tradition introducing and prepares dicyano methene benzo tetrahydrochysene
The method of furan derivatives, this method can obtain high yield dicyano methene benzo tetrahydrofuran derivatives DCM-OH-
CHO.Importantly, DCM-OH-CHO prepared by this method is comprising an activity hydroxy and aldehyde radical, can be by between functional group
Synthesis other dicyano methene benzo tetrahydrofuran derivatives, increased the practicality in other areas of this material
Property.
3rd, method of the present invention quantum yield can reach more than 80%, and product stability is high：Traditional dicyano first
Thiazolinyl benzo tetrahydrofuran derivatives are subjected to intramolecular aggregation quenching effect mostly, and fluorescence quantum yield is not high.In addition, there will be text
Offer the parameters such as the fluorescent stability to these materials not further investigate.In the present invention, in traditional dicyano methene
Intramolecular hydrogen bond unit is introduced in benzo tetrahydrofuran derivatives DCM-OH skeletons not only reduces intermolecular aggregation quenching effect, also
One stable rigid structure is provided.Therefore, its fluorescence quantum yield and photostability are substantially increased.Compare traditional DCM-
OH, the new DCM-OH-CHO for synthesizing shows excellent in different water phases and organic phase ratio, pH value, organic solvent, buffer system
Fluorescent stability, therefore in actual applications will be with obvious advantage.
Description of the drawings
Fig. 1 is the present invention by the synthesis path figure that DCM-OH is that raw material prepares DCM-OH-CHO, as shown in Figure 1, Jing Guojian
Single one-step synthesis can prepare DCM-OH-CHO；The synthesis is carried out in a mild condition, reacts 5 hours, you can obtain
(embodiment 1-3, yield is more than 80%) to target product.
Fig. 2 is the hydrogen spectrum of DCM-OH-CHO prepared by the present invention, and as shown in Figure 2, the product for preparing is purer；It is low
It is the proton resonance signal of hydroxyl at the 11.4ppm of field, illustrates that the hydrogen bond existed in DCM-OH-CHO molecules between hydroxyl and aldehyde radical is made
With.
Fig. 3 is the infrared spectrogram of DCM-OH-CHO prepared by the present invention, from the figure 3, it may be seen that 2820 and 2918cm-1Locate as hydroxyl
The characteristic peak of base, 1630cm-1Locate the characteristic peak for aldehyde radical, illustrate that the embodiment of the present invention successfully prepares DCM-OH-CHO.
Fig. 4 is the mass spectrum of DCM-OH-CHO prepared by the present invention, and as shown in Figure 4, the peak at 338.9 is DCM-OH-CHO point
Daughter ion peak, illustrates that the embodiment of the present invention successfully prepares DCM-OH-CHO.
Fig. 5 is the UV-visible absorption spectrum of DCM-OH-CHO prepared by the present invention and tradition DCM-OH, and Fig. 5 shows
DCM-OH-CHO molar absorptivities prepared by the present invention are higher than tradition DCM-OH.
Fig. 6 is the fluorescence emission spectrogram of compound of DCM-OH-CHO prepared by the present invention and tradition DCM-OH, and Fig. 6 shows the present invention
Prepared DCM-OH-CHO fluorescence quantum yields are apparently higher than traditional DCM-OH.
Fig. 7 is that DCM-OH-CHO prepared by the present invention and tradition DCM-OH send out in different water phases and fluorescence of the organic phase than in
Penetrate spectrogram, Fig. 7 shows to introduce hydrogen bond receptor aldehyde radical in traditional DCM-OH molecules can effectively be reduced intermolecular aggregation and be quenched
Effect, improves its fluorescence quantum yield.
Fig. 8 is fluorescence emission spectrogram of compound of traditional DCM-OH in different pH, and Fig. 9 is DCM-OH-CHO prepared by the present invention
Fluorescence emission spectrogram of compound in different pH, Fig. 8 and Fig. 9 show that the anti-pH of DCM-OH-CHO prepared by the present invention are higher than tradition
DCM-OH。
Figure 10 is DCM-OH-CHO prepared by the present invention and fluorescence emissions of the tradition DCM-OH in different organic solvents
Spectrogram, Figure 11 is fluorescence emission spectrogram of compound of traditional DCM-OH in different organic solvents, and Figure 10 and Figure 11 shows institute of the present invention
Fluorescent stabilities of the DCM-OH-CHO of preparation in different solvents is higher than tradition DCM-OH.
Figure 12 is fluorescence emission spectrogram of compound of traditional DCM-OH in different buffer systems, and Figure 13 is prepared by the present invention
Fluorescence emission spectrogram of compound of the DCM-OH-CHO in different buffer systems, Figure 12 and 13 shows the DCM-OH- prepared by the present invention
Fluorescent stabilities of the CHO in different buffer systems is higher than tradition DCM-OH.
Figure 14 is DCM-OH-CHO prepared by the present invention and fluorescent emissions of the tradition DCM-OH under different light irradiation durations
Spectrogram, Figure 14 shows outstanding anti-light Bleachability of the DCM-OH-CHO inheriting tradition DCM-OH prepared by the present invention.
Specific embodiment
With reference to embodiment, the present invention is described further.
Embodiment 1
270 milligrams of DCM-OH and 224 milligram of hexamethylenetetramines are accurately weighed in dry round-bottomed flask, 8 are subsequently adding
Milliliter trifluoroacetic acid, is heated to reflux 5 hours；After reaction terminates, room temperature is cooled to, is added in saturated sodium bicarbonate solution and many
Spent acid liquid, extracts organic matter and uses anhydrous sodium sulfate drying with dichloromethane；Vacuum distillation removes solvent, residue silica gel color
Spectrum post separation purification (dichloromethane is eluant, eluent) obtains a large amount of DCM-OH-CHO (yield is higher than 84%).The Structural Identification of product
Accompanying drawing 1-14 and description of the drawings are asked for an interview with Performance Testing.
Embodiment 2
270 milligrams of DCM-OH and 224 milligram of hexamethylenetetramines are accurately weighed in dry round-bottomed flask, 15 are subsequently adding
Milliliter trifluoroacetic acid, is heated to reflux 5 hours；After reaction terminates, room temperature is cooled to, is added in saturated sodium bicarbonate solution and many
Spent acid liquid, extracts organic matter and uses anhydrous sodium sulfate drying with dichloromethane；Vacuum distillation removes solvent, residue silica gel color
Spectrum post separation purification (dichloromethane is eluant, eluent) obtains a large amount of DCM-OH-CHO (yield is 85%).
Embodiment 3
270 milligrams of DCM-OH and 224 milligram of hexamethylenetetramines are accurately weighed in dry round-bottomed flask, 20 are subsequently adding
Milliliter trifluoroacetic acid, is heated to reflux 5 hours；After reaction terminates, room temperature is cooled to, is added in saturated sodium bicarbonate solution and many
Spent acid liquid, extracts organic matter and uses anhydrous sodium sulfate drying with dichloromethane；Vacuum distillation removes solvent, residue silica gel color
Spectrum post separation purification (dichloromethane is eluant, eluent) obtains a large amount of DCM-OH-CHO (yield is 86%).
Embodiment 4
270 milligrams of DCM-OH and 56 milligram of hexamethylenetetramines are accurately weighed in dry round-bottomed flask, 8 millis are subsequently adding
Trifluoroacetic acid is risen, 5 hours are heated to reflux；After reaction terminates, room temperature is cooled to, it is in saturated sodium bicarbonate solution and unnecessary to add
Acid solution, extracts organic matter and uses anhydrous sodium sulfate drying with dichloromethane；Vacuum distillation removes solvent, residue silica gel chromatograph
Post separation purification (dichloromethane is eluant, eluent) obtains a small amount of DCM-OH-CHO (yield is 22%).
Embodiment 5
270 milligrams of DCM-OH and 896 milligram of hexamethylenetetramines are accurately weighed in dry round-bottomed flask, 8 are subsequently adding
Milliliter trifluoroacetic acid, is heated to reflux 5 hours；After reaction terminates, room temperature is cooled to, is added in saturated sodium bicarbonate solution and many
Spent acid liquid, extracts organic matter and uses anhydrous sodium sulfate drying with dichloromethane；Vacuum distillation removes solvent, and crude product carries out nuclear-magnetism
Characterize, it was demonstrated that the dicyano methene benzo tetrahydrochysene of generating portion DCM-OH-CHO (yield is 41%) and part containing two aldehyde radicals
Furan derivatives.
Embodiment 6
270 milligrams of DCM-OH and 224 milligram of hexamethylenetetramines are accurately weighed in dry round-bottomed flask, 8 are subsequently adding
Milliliter trifluoroacetic acid, is heated to reflux 1 hour；After reaction terminates, room temperature is cooled to, TLC point board monitorings find big content of starting materials not
Reaction is complete, and the amount for generating DCM-OH-CHO is few.
Embodiment 7
270 milligrams of DCM-OH and 224 milligram of hexamethylenetetramines are accurately weighed in dry round-bottomed flask, 8 are subsequently adding
Milliliter trifluoroacetic acid, is heated to reflux 12 hours；After reaction terminates, room temperature is cooled to, adds saturated sodium bicarbonate solution neutralization
Unnecessary acid solution, extracts organic matter and uses anhydrous sodium sulfate drying with dichloromethane；Vacuum distillation removes solvent, and crude product carries out core
Magnetic is characterized, it was demonstrated that the dicyano methene benzo four of generating portion DCM-OH-CHO (yield is 38%) and part containing two aldehyde radicals
Hydrogen furan derivatives.
Embodiment 8
Trifluoroacetic acid is substituted with hydrochloric acid, other experiment parameters are with embodiment 2.After reaction terminates, a small amount of target product is obtained
DCM-OH-CHO (yield is 33%).
Embodiment 9
Trifluoroacetic acid is substituted with acetic acid, other experiment parameters are with embodiment 2.After reaction terminates, a small amount of target product is obtained
DCM-OH-CHO (yield is 37%).
Embodiment 10
With acetate and hydrochloride mixed liquor, (volume ratio is 1:2) trifluoroacetic acid is substituted, other experiment parameters are with embodiment 2.Instead
After should terminating, obtain a small amount of target product DCM-OH-CHO (yield is 35%).
Embodiment 11
With acetate and hydrochloride mixed liquor, (volume ratio is 2:1) trifluoroacetic acid is substituted, other experiment parameters are with embodiment 2.Instead
After should terminating, obtain a small amount of target product DCM-OH-CHO (yield is 37%).
Embodiment 12
With acetate and hydrochloride mixed liquor, (volume ratio is 1:1) trifluoroacetic acid is substituted, other experiment parameters are with embodiment 2.Instead
After should terminating, obtain a small amount of target product DCM-OH-CHO (yield is 39%).
Claims (8)
1. a kind of dicyano methene benzo tetrahydrofuran derivatives, is characterized in that, molecular formula is：
2. the preparation method of dicyano methene benzo tetrahydrofuran derivatives described in claim 1, is characterized in that, including following
Step：
(1) with DCM-OH as raw material, hexamethylenetetramine and acid are added, is well mixed, obtain mixed liquor；The mixture formula ratio
Example be：
270 milligrams of DCM-OH
Hexamethylenetetramine 56-1120 milligrams
The volume 8-20 milliliter of acid；
The molecular formula of wherein described DCM-OH is：
One or more of the acid in hydrochloric acid, acetic acid and trifluoroacetic acid；
(2) by above-mentioned mixed-liquor return 1-10 hours；
(3) after reaction terminates, it is cooled to room temperature；Neutralization remaining acid solution, extracts organic substance, is dried organic phase, and vacuum distillation is removed
Solvent is removed, crude product is obtained；
(4) target product is obtained after the crude product purified by silica gel chromatographic purification.
3. the preparation method of dicyano methene benzo tetrahydrofuran derivatives according to claim 2, is characterized in that, step
(1) the mixture formula ratio is：
270 milligrams of DCM-OH
Hexamethylenetetramine 224-896 milligrams
The volume 8-20 milliliter of acid.
4. the preparation method of dicyano methene benzo tetrahydrofuran derivatives according to claim 3, is characterized in that, step
(1) the mixture formula ratio is：
270 milligrams of DCM-OH
Hexamethylenetetramine (HMT) 224-560 milligrams
The volume 8-20 milliliter of acid.
5. according to the preparation method of one of claim 2-4 dicyano methene benzo tetrahydrofuran derivatives, its feature
It is that step (1) acid is trifluoroacetic acid.
6. according to the preparation method of one of claim 2-4 dicyano methene benzo tetrahydrofuran derivatives, its feature
It is that step (2) is to react 5 hours to 10 hours under reflux.
7. according to the preparation method of one of claim 2-4 dicyano methene benzo tetrahydrofuran derivatives, its feature
It is that step (3) is to adopt in saturated sodium bicarbonate solution and unnecessary acid solution, uses dichloromethane extracting of organic compounds.
8. according to the preparation method of one of claim 2-4 dicyano methene benzo tetrahydrofuran derivatives, its feature
It is that step (4) separating-purifying is as eluant, eluent using dichloromethane.
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| CN109053711A (en) * | 2018-09-21 | 2018-12-21 | 衡阳师范学院 | A kind of probe compound and its preparation method and application for mercury ion detecting |
| CN112778288A (en) * | 2021-01-22 | 2021-05-11 | 湖南大学 | Near-infrared solid-state light-emitting fluorescent probe and preparation method and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN109053711A (en) * | 2018-09-21 | 2018-12-21 | 衡阳师范学院 | A kind of probe compound and its preparation method and application for mercury ion detecting |
| CN112778288A (en) * | 2021-01-22 | 2021-05-11 | 湖南大学 | Near-infrared solid-state light-emitting fluorescent probe and preparation method and application thereof |
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