CN107602469A - It is a kind of that there is aggregation-induced emission enhancement, the naphthalimide compound of solvent discoloration and self- recoverage power mutagens color property and application - Google Patents
It is a kind of that there is aggregation-induced emission enhancement, the naphthalimide compound of solvent discoloration and self- recoverage power mutagens color property and application Download PDFInfo
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Abstract
There is aggregation-induced emission enhancement, the naphthalimide compound of solvent discoloration and self- recoverage power mutagens color property and application the present invention relates to a kind of.It has the structure described in formula 1.This compound is luminous very weak among solution, and one is aggregated, shows strong green fluorescence, shows obvious aggregation-induced emission enhancement property.Meanwhile this compound can also show different fluorescence colors among the solvent of opposed polarity, so as to show solvent discoloration characteristic.In addition, the solid sample of this compound fluorescence after mechanical lapping can be changed into green from blue-green, and the solid sample after grinding can revert to corresponding blue-green fluorescent after room temperature is placed with spontaneous, so as to show the power mutagens color property with self- recoverage behavior.Therefore this compound is expected to apply in fields such as luminescent material, sensor and optoelectronic devices.
Description
Technical field
The present invention relates to a kind of intellectual material of mechanical force-responsive of novel high solid luminescent and its application, particularly relate to
And have aggregation-induced emission enhancement, solvent discoloration and self- recoverage power mutagens color property while a kind of new contains naphthalimide
The compound of structure and application.
Background technology
Traditional luminescent material often shows strong fluorescence under solution condition, is quenched yet with caused by aggregation
Effect causes them to show fainter fluorescence under the coherent condition such as solid or film.It is well known that in actual life
Among work, almost all of luminescent material all uses under aggregation conditions, therefore the presence of quenching effect caused by aggregation
It is unfavorable for their applications in real life.With the fluorescence molecule with quenching effect caused by aggregation on the contrary, with aggregation
Induced luminescence or the fluorescence molecule of aggregation-induced emission enhancement property often show strong fluorescence in the collected state, this
It is highly profitable for the practical application of these fluorescence molecules.There is the intellectual material of response to outside stimulus due to sensing
Device, memory chip, safety ink, data storage and the field such as false proof have potential application prospect, so as to cause section
The extensive concern of scholar person.According to different stimulation modes, these stimuli responsive materials can be divided into power cause off-color material,
The several types such as thermochromic material, photochromic material, electrochromic material and gas-discoloration material.In this several intelligence
Among material, power causes off-color material to have become current study hotspot.Outer by mechanical lapping, scraping or friction etc.
Under portion's incentive condition, power causes the glow color of off-color material or intensity to change, and the power mutagens to change
Color material can return to initial state by heating or solvent are stifling.In the last few years, can be beamed back certainly after color change
Self- recoverage power to initial conditions causes off-color material to cause the great research interest of researchers.With self- recoverage power mutagens color
The material of property can return to initial state under conditions of without extra process from reversible.Therefore, compared to can not
For self-healing power causes off-color material, off-color material is caused in actual applications with bigger advantage with self-healing power.
In addition, it is contemplated that the compound with aggregation-induced emission and aggregation-induced emission enhancement property tends in the solid state
Strong fluorescence is shown, therefore develops the stimuli responsive with aggregation-induced emission or aggregation-induced emission enhancement behavior
Material has broad application prospects.So far, it is to have very much that the power with self- recoverage property, which causes the quantity of electrochromic compound,
Limit, and it is even more few to have the quantity of the compound of aggregation-induced emission enhancement and self- recoverage power mutagens color property simultaneously
It is few.Compound with solvent discoloration property can show different glow colors, this kind ofization in the solvent of opposed polarity
Compound has important value in field of light emitting materials.Therefore, develop while there is aggregation-induced emission enhancement, solvent discoloration
Compound with self- recoverage power mutagens color property is very significant.
The content of the invention
The technical problems to be solved by the invention, which are to provide, a kind of has aggregation-induced emission enhancement, solvent discoloration and from extensive
The naphthalimide compound of multiple power mutagens color property and application.
In order to solve the above technical problems, the technical solution adopted by the present invention is：
A kind of naphthalimide with aggregation-induced emission enhancement, solvent discoloration and self- recoverage power mutagens color property is provided
Compound, it has the structure described in formula 1：
A kind of naphthalimide with aggregation-induced emission enhancement, solvent discoloration and self- recoverage power mutagens color property is provided
The preparation method of compound, comprises the following steps:
1) diphenyl methane is made into solvent in THF, n-BuLi makees highly basic, under conditions of nitrogen protection and 4- bromine hexichol first
Ketone adds p-methyl benzenesulfonic acid work acid after substitution reaction occurs, and toluene makees solvent, elimination reaction occurs under conditions of nitrogen protection, obtains
To the tetraphenyl ethylene derivative 1-1 of single bromine substitution；
2) the tetraphenyl ethylene derivative 1-1 that the single bromine for obtaining step 1) substitutes makees solvent in THF, and n-BuLi is made strong
Alkali, the tetraphenyl ethylene through the obtained boration of hydrochloric acid acidifying spreads out after substitution reaction occurs with trimethylborate under conditions of nitrogen protection
Biological 1-2；
3) 4- bromo- 1,8- naphthalic anhydrides are substituted under conditions of ethanol as solvent, nitrogen protection with n-butylamine
Reaction, obtains 1,8- naphthalimide derivatives 1-3；
4) tetraphenyl ethylene for being acidified the 1,8- naphthalimide derivatives 1-3 that step 3) the obtains boracics obtained with step 2)
Derivative 1-2 makees mixed solvent in toluene, second alcohol and water, and potassium carbonate makees alkali, and four (triphenyl phosphorus) palladiums make catalyst, nitrogen protection
Under conditions of coupling reaction occurs, obtain target compound 1.
In such scheme, the preparation method of the compound 1 specifically includes following steps：
1) under the conditions of nitrogen atmosphere, diphenyl methane is added in the THF solvents for having been drained off air, stirs, add
Enter n-BuLi and 4- bromine benzophenone, carry out substitution reaction, after reaction terminates, by white crude product, p-methyl benzenesulfonic acid and
Toluene through discharging air, which adds to vacuumize, fills N2In reaction vessel afterwards, elimination reaction is carried out, after reaction terminates, post processing,
Obtain white solid product 1-1；
2) under the conditions of nitrogen atmosphere, by white solid product 1-1 that step 1) obtains, n-BuLi and sky is had been drained off
The THF of gas, which adds to vacuumize, fills N2In reaction vessel afterwards, add trimethylborate and hydrochloric acid, the substitution for carrying out boration are anti-
Should, after reaction terminates, post processing, obtain white solid product 1-2；
3) under the conditions of nitrogen atmosphere, bromo- 1, the 8- naphthalic anhydrides of 4- are added to the alcohol solvent for having been drained off air
In, stirring, n-butylamine is added, carry out substitution reaction, after reaction terminates, post processing, obtain white solid product 1-3；
4) under the conditions of nitrogen atmosphere, 1,8- naphthalimide derivatives 1-3, potassium carbonate, four (triphens that step 3) is obtained
Base phosphorus) palladium and have been drained off the toluene of air, ethanol, the mixed solvent of water and add to vacuumize and fill N2In reaction vessel afterwards, add
Enter the tetraphenyl ethylene derivative 1-2 for the boracic acidifying that step 2) obtains, coupling reaction occurs, after reaction terminates, post processing, obtain
Target product white solid product 1.
In such scheme, the mol ratio of diphenyl methane and 4- bromine benzophenone is 1.2 in step 1):1 to 1.3:1 it
Between.
In such scheme, the mol ratio of diphenyl methane and n-BuLi is 1.2 in step 1):1 to 1.1:Between 1.
In such scheme, the mol ratio of diphenyl methane and p-methyl benzenesulfonic acid is 6.5 in step 1):1 to 6.7:Between 1.
In such scheme, in step 1)：Diphenyl methane is added to the THF for having been drained off air under the conditions of 0 DEG C -2 DEG C
In solvent, add and react 1-2 hours after n-BuLi under the conditions of 0 DEG C -2 DEG C in nitrogen atmosphere, then add 4- bromine hexichol first
6-7 hours are reacted at room temperature after ketone, p-methyl benzenesulfonic acid is eventually adding and has been drained off after the toluene of air in 110 DEG C of -120 DEG C of conditions
Lower elimination reaction 6-8 hours.
In such scheme, step 1) obtains in step 2) compound 1-1 and the mol ratio of trimethylborate are 1:2.1~
1:Between 2.2.
In such scheme, in step 2)：N-BuLi is added under the conditions of -78 DEG C to -80 DEG C to be produced containing white solid
In product 1-1 and the THF for having been drained off air reaction vessel, 3-4 hours are stirred under the conditions of maintaining the temperature at -78 DEG C to -80 DEG C,
Then trimethylborate is added, reaction 12-13 hours are stirred at room temperature, adds hydrochloric acid terminating reaction.
In such scheme, the mol ratio of bromo- 1, the 8- naphthalic anhydrides of 4- and n-butylamine is 1 in step 3):1.1 to 1:1.2
Between.
In such scheme, in step 3)：The bromo- 1,8- naphthalic anhydrides of 4- are added to the alcohol solvent for having been drained off air
In, add and react 12-13 hours after n-butylamine under the conditions of 78 DEG C -80 DEG C in nitrogen atmosphere.
In such scheme, mole for the compound 1-2 that step 3) obtains in step 4) compound 1-3 obtains with step 2)
Than for 2:2.05 to 2:Between 2.15.
In such scheme, in step 4)：Return stirring reacts 16-18 hours under the conditions of coupling reaction is 80 DEG C to 85 DEG C,
And the volume ratio of toluene, second alcohol and water is 9:9:1 to 11:11:Between 1.
In such scheme, the post processing in step 1) is：With 10% NaHCO3Solution three after aqueous solution washing reaction
It is secondary, the organic phase anhydrous Na of merging2SO4Dry, screw out solvent, pillar layer separation；In step 2), step 3) and step 4)
Post-process and be：With dichloromethane extraction three times, organic layer is washed three times with saturated common salt after extraction, and the organic phase of merging is with anhydrous
Na2SO4Dry, screw out solvent, pillar layer separation.
Above-mentioned while containing naphthalimide structure, has aggregation-induced emission enhancement, solvent discoloration and self- recoverage power mutagens color
Application of the compound of property in the self- recoverage power mutagens color Intelligent luminous material for preparing height solid luminescent.
Beneficial effects of the present invention：
Compound provided by the invention is that a kind of new while containing naphthalimide structure have aggregation-induced emission increasing
By force, solvent discoloration and the fluorescent material of self- recoverage power mutagens color property.This compound luminous very weak, Yi Jingju among solution
Collection then shows strong green fluorescence, shows obvious aggregation-induced emission enhancement property.Meanwhile this compound is not
Different fluorescence colors can also be shown among the solvent of same polarity, so as to show solvent discoloration characteristic.In addition, thisization
The solid sample of compound fluorescence after mechanical lapping can be changed into green from blue-green, and the solid sample after grinding passes through
Room temperature can revert to corresponding blue-green fluorescent after placing with spontaneous, so as to show the power mutagens color with self- recoverage behavior
Property.Therefore, this compound is expected to apply in fields such as luminescent material, mechanics sensor and optoelectronic devices.
Brief description of the drawings
Fig. 1 be compound 1 in DMF and water mixed solvent along with different volumes fraction water (0%-90%) under the conditions of
Luminescence generated by light spectrogram (excitation wavelength 400nm).
Fig. 2 is compound 1 in toluene, tetrahydrofuran (THF), dichloromethane (CH2Cl2), N,N-dimethylformamide
And the luminescence generated by light spectrogram (excitation wavelength 400nm) in dimethyl sulfoxide (DMSO) (DMSO) solvent (DMF).
Fig. 3 is the solid powder after the solid powder of compound 1, mechanical force grinding and the solid powder room temperature after grinding
Place the luminescence generated by light spectrogram (excitation wavelength 375nm) after 1 hour self- recoverage.
Embodiment
Embodiment 1：The synthesis of compound 1
Synthetic route is as follows：
N-BuLi is n-BuLi in reaction equation, and THF is tetrahydrofuran, and p-toluenesulfonic acid are to toluene
Sulfonic acid, toluene are toluene, B (OMe)3For trimethyl borate, HCl is hydrochloric acid, Pd (PPh3)4For four (triphenyl phosphorus) palladiums,
Ethanol is ethanol, K2CO3For potassium carbonate, water is water.
Specific synthesis step is as follows：
1st, under conditions of 0 DEG C of temperature, 100ml three-necked flasks is vacuumized and fill N2After three times, 12mmol hexichol is added
Methylmethane and 50ml by water removal drying process and discharge the tetrahydrofuran of air, slowly squeeze into 10mmol n-BuLi,
Nitrogen atmosphere is always maintained at, 0 DEG C occurs n-BuLi and pulls out hydrogen reaction 1 hour, adds 9.5mmol 4- bromine benzophenone, reaction
Room temperature is returned to, is stirred 6 hours, saturated aqueous ammonium chloride is added and stops reaction, organic phase CH2Cl2Extraction, is eaten with saturation
Salt is washed three times, then uses anhydrous Na2SO4Dry, organic solvent is screwed out, by residue, 1.8mmol p-methyl benzenesulfonic acid and 60ml first
Benzene is added to bis- mouthfuls of flasks of 100ml, back flow reaction 6-8 hours, is cooled to room temperature, organic layer with 10% NaHCO3The aqueous solution is washed
Three times, the organic phase anhydrous Na of merging2SO4Dry, steam solvent toluene, pillar layer separation obtains white solid
Product 1-1.Yield：73%.
2nd, 250ml three-necked flasks are vacuumized and fills N2After three times, 10mmol compound 1-1 are added, add 120ml by removing
Water drying process and the tetrahydrofuran for discharging air, under the conditions of -78 DEG C, 12mmol n-BuLis are slowly squeezed into, stirring 3 is small
When, 21mmol trimethylborates are slowly squeezed into, return to room temperature, are stirred 12 hours, add 10ml hydrochloric acid terminating reactions, organic phase
Use CH2Cl2Extraction, organic layer is washed three times with saturated common salt after extraction, the organic phase anhydrous Na of merging2SO4Dry, screw out
Organic solvent, pillar layer separation obtain white solid product 1-2.Yield：81%.
3rd, under the conditions of nitrogen atmosphere, bromo- 1, the 8- naphthalic anhydrides of 10mmol 4- is added to and have been drained off air
In 50ml alcohol solvents, stirring, 10mmol n-butylamines are added, carry out substitution reaction 12 hours, after reaction terminates, organic phase is used
CH2Cl2Extraction, organic layer is washed three times with saturated common salt after extraction, the organic phase anhydrous Na of merging2SO4Dry, back-out has
Solvent, pillar layer separation obtain white solid product 1-3.Yield：87%.
4th, 100ml three-necked flasks are vacuumized and fills N2After three times, 2.1mmol compounds 1-2,2mmol compound 1- is added
3,0.5g potassium carbonate, 50ml toluene, 50ml ethanol, 5ml water, nitrogen atmosphere is always maintained at, stirring at normal temperature 40 minutes, adds 0.1g
Catalyst four (triphenyl phosphorus) palladium, 80 DEG C of backflows, is stirred 16 hours, recovers room temperature, and organic layer is washed three times with saturated common salt, had
Machine mutually uses anhydrous Na2SO4Dry, steam solvent toluene, pillar layer separation obtains white solid product 1.Yield：
80%.1:1H NMR(400MHz,CDCl3):δ (ppm)=8.57-8.53 (m, 2H), 8.12 (d, J=12Hz, 1H), 7.68-
7.58 (m, 2H), 7.19-6.99 (m, 19H), 4.14 (t, J=6Hz, 2H), 1.67 (t, J=8Hz, 2H), 1.40 (t, J=
8Hz, 2H), 0.92 (t, J=6Hz, 3H) .Anal.Calcd for C42H33NO2：C,86.42；H,5.70；N,2.40.Found:
C,86.47；H,5.76；N,2.37.
The product 1 (2 × 10 of the embodiment-5Mol/L) along with different volumes fraction water in DMF and water mixed solvent
Luminescence generated by light spectrogram (excitation wavelength 400nm) under the conditions of (0%-90%) is as shown in Figure 1.By Fig. 1 it will be seen that
Product 1 shows faint luminescence generated by light signal in neat solvent, and is continuously increased (especially water content with aggregation extent
After 40%), the luminescence generated by light signal of product 1 significantly increases.Therefore, product 1 can show excellent aggregation inducing hair
Light is enhanced propertied.
The embodiment product 1 (2 × 10-5Mol/L) in toluene, tetrahydrofuran (THF), dichloromethane (CH2Cl2)、N,N-
Luminescence generated by light spectrogram (excitation wavelength 400nm) in dimethylformamide (DMF) and dimethyl sulfoxide (DMSO) (DMSO) solvent is such as
Shown in Fig. 2.By Fig. 2 it will be seen that with the increase of solvent polarity, fluorescence emission peak shows showing for gradual red shift
As.Therefore, product 1 can show solvent effect.
Solid powder after the solid powder of the embodiment product 1, mechanical force grinding and the solid powder room after grinding
Luminescence generated by light spectrogram (excitation wavelength 375nm) after temperature 1 hour self- recoverage of placement is as shown in Figure 3.By Fig. 3, we can see
Going out, the solid sample of product 1 shows blue-green fluorescent, and after grinding, sample shows green fluorescence, and after grinding
Sample fluorescence after room temperature is placed 1 hour returns to blue-green again.Therefore, product 1 shows the power mutagens of self recovery
Color property.There is product 1 aggregation-induced emission enhancement, solvent discoloration and self- recoverage power to cause discolouration while being extremely rare
The luminophor of matter, it is expected to apply in fields such as luminescent material, force snesor, anti-counterfeiting mark and optoelectronic devices.
Claims (10)
1. a kind of naphthalimide compound with aggregation-induced emission enhancement, solvent discoloration and self- recoverage power mutagens color property,
It is characterized in that：It has the structure described in formula 1：
2. the preparation method of the naphthalimide compound described in claim 1, it is characterised in that：Comprise the following steps：
1) diphenyl methane is made into solvent in THF, n-BuLi is made highly basic, sent out under conditions of nitrogen protection with 4- bromines benzophenone
P-methyl benzenesulfonic acid is added after raw substitution reaction and makees acid, toluene makees solvent, elimination reaction occurs under conditions of nitrogen protection, obtains list
The tetraphenyl ethylene derivative 1-1 of bromine substitution；
2) the tetraphenyl ethylene derivative 1-1 that the single bromine for obtaining step 1) substitutes makees solvent in THF, and n-BuLi makees highly basic, nitrogen
The tetraphenyl ethylene derivative that boration is made is acidified through hydrochloric acid after substitution reaction occurs with trimethylborate under conditions of gas shielded
1-2；
3) under conditions of ethanol as solvent, nitrogen protection with n-butylamine substitution reaction is occurred into for 4- bromo- 1,8- naphthalic anhydrides,
Obtain 1,8- naphthalimide derivatives 1-3；
4) tetraphenyl ethylene that the 1,8- naphthalimide derivatives 1-3 that step 3) the obtains boracics obtained with step 2) are acidified is derived
Thing 1-2 makees mixed solvent in toluene, second alcohol and water, and potassium carbonate makees alkali, and four (triphenyl phosphorus) palladiums make catalyst, the bar of nitrogen protection
Coupling reaction occurs under part, obtains target compound 1.
3. the preparation method of naphthalimide compound according to claim 2, it is characterised in that：
1) under the conditions of nitrogen atmosphere, diphenyl methane is added in the THF solvents for having been drained off air, stirred, added just
Butyl lithium and 4- bromine benzophenone, substitution reaction is carried out, after reaction terminates, white crude product and has been arranged p-methyl benzenesulfonic acid
The toluene for going out air adds and vacuumizes and fill N2In reaction vessel afterwards, elimination reaction is carried out, after reaction terminates, post processing, is obtained
White solid product 1-1；
2) under the conditions of nitrogen atmosphere, by white solid product 1-1 that step 1) obtains, n-BuLi and air is had been drained off
THF, which adds to vacuumize, fills N2In reaction vessel afterwards, trimethylborate and hydrochloric acid are added, carries out the substitution reaction of boration, instead
After should terminating, post processing, white solid product 1-2 is obtained；
3) under the conditions of nitrogen atmosphere, bromo- 1, the 8- naphthalic anhydrides of 4- is added in the alcohol solvent for having been drained off air, stirred
Mix, add n-butylamine, carry out substitution reaction, after reaction terminates, post processing, obtain white solid product 1-3；
4) under the conditions of nitrogen atmosphere, 1,8- naphthalimide derivatives 1-3, potassium carbonate, four (triphenyls that step 3) is obtained
Phosphorus) palladium and have been drained off the toluene of air, ethanol, the mixed solvent of water and add to vacuumize and fill N2In reaction vessel afterwards, add
The tetraphenyl ethylene derivative 1-2 for the boracic acidifying that step 2) obtains, occurs coupling reaction, after reaction terminates, post processing, obtains mesh
Mark product as white solid product 1.
4. the preparation method of naphthalimide compound according to claim 2, it is characterised in that：Diphenylmethyl in step 1)
The mol ratio of alkane and 4- bromine benzophenone is 1.2:1 to 1.3:Between 1；Mole of diphenyl methane and n-BuLi in step 1)
Than for 1.2:1 to 1.1:Between 1；The mol ratio of diphenyl methane and p-methyl benzenesulfonic acid is 6.5 in step 1):1 to 6.7:1 it
Between.
5. the preparation method of naphthalimide compound according to claim 2, it is characterised in that：Step 1) obtains in step 2)
The compound 1-1 and the mol ratio of trimethylborate arrived is 1:2.1~1:Between 2.2.
6. the preparation method of naphthalimide compound according to claim 2, it is characterised in that：4- bromo- 1 in step 3),
The mol ratio of 8- naphthalic anhydrides and n-butylamine is 1:1.1 to 1:Between 1.2.
7. the preparation method of naphthalimide compound according to claim 2, it is characterised in that：Step 3) obtains in step 4)
To the obtained compound 1-2 mol ratio of compound 1-3 and step 2) be 2:2.05 to 2:Between 2.15.
8. the preparation method of naphthalimide compound according to claim 2, it is characterised in that：
Diphenyl methane is added under the conditions of 0 DEG C -2 DEG C in the THF solvents for having been drained off air in step 1), adds normal-butyl
React 1-2 hours after lithium under the conditions of 0 DEG C -2 DEG C in nitrogen atmosphere, room temperature reaction 6-7 is small after then adding 4- bromine benzophenone
When, it is eventually adding p-methyl benzenesulfonic acid and elimination reaction 6-8 is small under the conditions of 110 DEG C -120 DEG C after the toluene for having been drained off air
When；
In step 2)：N-BuLi is added to containing white solid product 1-1 and had been drained off under the conditions of -78 DEG C to -80 DEG C
In the THF of air reaction vessel, 3-4 hours are stirred under the conditions of maintaining the temperature at -78 DEG C to -80 DEG C, then add boric acid three
Methyl esters, reaction 12-13 hours are stirred at room temperature, add hydrochloric acid terminating reaction；
In step 3)：Bromo- 1, the 8- naphthalic anhydrides of 4- are added in the alcohol solvent for having been drained off air, add n-butylamine after
12-13 hours are reacted in nitrogen atmosphere under the conditions of 78 DEG C -80 DEG C；
In step 4)：Return stirring reacts 16-18 hours under the conditions of coupling reaction is 80 DEG C to 85 DEG C, and toluene, second alcohol and water
Volume ratio be 9:9:1 to 11:11:Between 1.
9. the preparation method of naphthalimide compound according to claim 2, it is characterised in that：Post processing in step 1)
For：With 10% NaHCO3Solution after aqueous solution washing reaction three times, the organic phase anhydrous Na of merging2SO4Dry, screw out
Solvent, pillar layer separation；Post processing in step 2), step 3) and step 4) is：With dichloromethane extraction three times, have after extraction
Machine layer is washed three times with saturated common salt, the organic phase anhydrous Na of merging2SO4Dry, screw out solvent, pillar layer separation.
10. the naphthalimide compound described in claim 1 causes intelligent color-changing glimmering in the self- recoverage power for preparing height solid luminescent
Application in luminescent material.
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| CN114933897A (en) * | 2022-03-11 | 2022-08-23 | 江西维邦生物科技有限公司 | Method for preparing aggregation-induced emission microspheres by swelling method and application thereof |
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