CN105199711B - Carbazole derivates are making pressure sensitivity luminous body or the application in pressure transducer as triboluminescent material - Google Patents
Carbazole derivates are making pressure sensitivity luminous body or the application in pressure transducer as triboluminescent material Download PDFInfo
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- CN105199711B CN105199711B CN201510562662.2A CN201510562662A CN105199711B CN 105199711 B CN105199711 B CN 105199711B CN 201510562662 A CN201510562662 A CN 201510562662A CN 105199711 B CN105199711 B CN 105199711B
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Abstract
The invention discloses a kind of application of carbazole derivates as triboluminescent material in pressure sensitivity luminous body or pressure transducer is made, the carbazole derivates have following general structure：, an integer wherein between n=1 11, and specifically disclose the preparation process of the carbazole derivates.The anhydrous system of anaerobic is adopted in the preparation process of the present invention, solvent used using front through purification process, and reacted under an inert atmosphere, prepared acicular crystal thing can see obvious blue light when scraping using metal spoon, therefore the tribo-luminescent performance of carbazole derivates makes which have preferable application prospect in pressure sensitivity luminous body or piezoelectric transducer is made as triboluminescent material.
Description
Technical field
The invention belongs to the synthesis technical field of triboluminescent material, and in particular to a kind of carbazole derivates are sent out as friction
Luminescent material is making pressure sensitivity luminous body or the application in pressure transducer.
Background technology
Tribo-luminescence（Triboluminescence, abridge TL）It is the phenomenon for referring to be converted into mechanical pressure luminous energy,
It is referred to as machinery luminous, which can realize the conversion of mechanical energy and luminous energy.Material with tribo-luminescent performance is referred to as
Triboluminescent material, which has an extensive potential using value, such as pressure sensitivity luminous body, pressure transducer, bill false proof and
Display components and parts of other scientific instrument etc..Triboluminescent with a long history, most earlier than 1620, Francis Bacon just remember
Sugar is carried and luminescence phenomenon can have been produced when being squeezed or rub；G. E. Hardy et al. have found coumarin, luxuriant and rich with fragrance or 9- anthracene second
The material with aromatic group such as alcohol has triboluminescent performance（Journal of the American Chemical
Society, 1977, 99, 3552-3558.）.But it is all that some have that above-mentioned discovery has the material of tribo-luminescent performance
The fluorescent material of specific crystal structure, and also no researcher clearly can intactly parse triboluminescent inherent machine so far
Reason.In addition, it is the coordination compound with center of asymmetry and inorganic compound, such as mixture ZnS- to study at present relatively large number of
Mn、Ca2Al2SiO2-Ce3+And SrAl2O4-Eu2+Deng.Up to the present, the research of organic triboluminescent material is less, therefore, tool
Have tribo-luminescent performance organic small molecule material exploitation to promote tribo-luminescent performance inherent mechanism research and industrialization
Using having great importance.
The content of the invention
Present invention solves the technical problem that there is provided a kind of carbazole derivates is making pressure sensitivity as triboluminescent material
Application in luminous body or pressure transducer.
To solve above-mentioned technical problem, the present invention adopts the following technical scheme that carbazole derivates exist as triboluminescent material
Make pressure sensitivity luminous body or the application in pressure transducer, it is characterised in that the carbazole derivates have following general structure：
,
An integer wherein between n=1-11, its concrete preparation process is：Reaction after processing through anhydrous and oxygen-free
The DMF and carbazole of solvent newly steaming are added in container, the sodium hydride that purity is 60% is then dividedly in some parts, is added
Bromo alkanol back flow reaction 8h are continuously added after sodium hydride stirring reaction 30min, is added water after reaction completely and reaction is quenched, use two
Chloromethanes are extracted three times, and anhydrous sodium sulfate drying is added after combined dichloromethane, are filtered to remove solid sodium sulfate, are collected organic
Phase, after rotary evaporation dichloromethane, Jing column chromatographies purification obtains target product carbazole derivates, then using normal hexane recrystallization
Obtain transparent acicular crystal thing.
Further preferably, the mol ratio of described carbazole, bromo alkanol and sodium hydride is 10:10:12.5.
Adopt the anhydrous system of anaerobic in the preparation process of the present invention, solvent used using front through purification process,
And reacted under an inert atmosphere, acicular crystal thing is obtained and obvious blue light can be seen when scraping using metal spoon,
Therefore the tribo-luminescent performance of carbazole derivates makes which make pressure sensitivity luminous body or piezoelectricity biography as triboluminescent material
There is in sensor preferable application prospect.
Specific embodiment
By the following examples the above of the present invention is described in further details, but this should not be interpreted as this
The scope for inventing above-mentioned theme is only limitted to below example, and all technologies realized based on the above of the present invention belong to this
Bright scope.
Embodiment 1
Magneton is added in the stoke flask of 100mL, solvent 50mL N, N- diformazans is added after anhydrous and oxygen-free process
Base Methanamide and 1.67g（10mmol）Carbazole, is then dividedly in some parts 0.5g（Purity 60%, 12.5mmol）Sodium hydride, adds hydrogenation
Sodium continuously adds 1.25g after standing 30min（10mmol）Ethylene bromohyrin back flow reaction 8h, add 50mL water quenchings after reaction completely
Go out reaction, extracted three times with dichloromethane（50mL*3）, anhydrous sodium sulfate drying is added after combined dichloromethane, sulfur is filtered to remove
Sour sodium solid, collects organic faciess, and after rotary evaporation removes dichloromethane, Jing column chromatography purification obtains target product carbazole derivates
（2.0g, 94%）, target product is recrystallized to give into acicular crystal thing using normal hexane then, the acicular crystal thing is using gold
Category spoon can see obvious blue light when scraping.
Embodiment 2
Magneton is added in the stoke flask of 100mL, solvent 50mL N, N- diformazans is added after anhydrous and oxygen-free process
Base Methanamide and 1.67g（10mmol）Carbazole, is then dividedly in some parts 0.5g（Purity 60%, 12.5mmol）Sodium hydride, adds hydrogenation
Sodium continuously adds 1.67g after standing 30min（10mmol）The bromo- 1- amylalcohols of 5- back flow reaction 8h, add 50mL after reaction completely
Water quenching is gone out reaction, is extracted three times with dichloromethane（50mL*3）, anhydrous sodium sulfate drying is added after combined dichloromethane, is crossed and is filtered
Remove solid sodium sulfate, collect organic faciess, Jing column chromatography purification obtains target product carbazole and spreads out after rotary evaporation removes dichloromethane
Then target product is recrystallized to give acicular crystal thing using normal hexane by biology, and the acicular crystal thing is using metal spoon
Obvious blue light can be seen during scraping.
Embodiment 3
Magneton is added in the stoke flask of 100mL, solvent 50mL N, N- diformazans is added after anhydrous and oxygen-free process
Base Methanamide and 1.67g（10mmol）Carbazole, is then dividedly in some parts 0.5g（Purity 60%, 12.5mmol）Sodium hydride, adds hydrogenation
Sodium continuously adds 2.09g after standing 30min（10mmol）The bromo- 1- capryl alcohol of 8- back flow reaction 8h, add 50mL after reaction completely
Water quenching is gone out reaction, is extracted three times with dichloromethane（50mL*3）, anhydrous sodium sulfate drying is added after combined dichloromethane, is crossed and is filtered
Solid sodium sulfate is removed, organic faciess are collected, Jing column chromatographies purification obtains target product carbazole derivates after rotary evaporation dichloromethane,
Then target product is recrystallized to give into acicular crystal thing using normal hexane, the acicular crystal thing is when scraping using metal spoon
Obvious blue light can be seen.
Embodiment 4
Magneton is added in the stoke flask of 100mL, solvent 50mL N, N- diformazans is added after anhydrous and oxygen-free process
Base Methanamide and 1.67g（10mmol）Carbazole, is then dividedly in some parts 0.5g（Purity 60%, 12.5mmol）Sodium hydride, adds hydrogenation
Sodium continuously adds 2.65g after standing 30min（10mmol）The bromo- DODECANOL, 1-s of 12- back flow reaction 8h, add after reaction completely
50mL water quenchings are gone out reaction, are extracted three times with dichloromethane（50mL*3）, after combined dichloromethane, add anhydrous sodium sulfate drying, mistake
Filter solid sodium sulfate, collect organic faciess, Jing column chromatographies purification obtains target product carbazole and spreads out after rotary evaporation dichloromethane
Then target product is recrystallized to give acicular crystal thing using normal hexane by biology, and the acicular crystal thing is using metal spoon
Obvious blue light can be seen during scraping.
Embodiment above describes ultimate principle, principal character and the advantage of the present invention.The technical staff of the industry should
Understand, the present invention is not restricted to the described embodiments, the original for simply illustrating the present invention described in above-described embodiment and description
Reason, under the scope without departing from the principle of the invention, the present invention also has various changes and modifications, and these changes and improvements each fall within
In the scope of protection of the invention.
Claims (2)
1. the preparation method of triboluminescent material carbazole derivates, it is characterised in that there is the carbazole derivates following structure to lead to
Formula：
,
An integer wherein between n=1-11, its concrete preparation process is：Reaction vessel after processing through anhydrous and oxygen-free
The middle DMF for adding solvent newly to steam and carbazole, are then dividedly in some parts the sodium hydride that purity is 60%, add hydrogenation
Bromo alkanol back flow reaction 8h are continuously added after sodium stirring reaction 30min, is added water after reaction completely and reaction is quenched, use dichloromethane
Alkane is extracted three times, and anhydrous sodium sulfate drying is added after combined dichloromethane, is filtered to remove solid sodium sulfate, collects organic faciess, rotation
After turning evaporation dichloromethane, Jing column chromatography purification obtains target product carbazole derivates, is then recrystallized to give using normal hexane
Bright acicular crystal thing.
2. the preparation method of triboluminescent material carbazole derivates according to claim 1, it is characterised in that：Described click
The mol ratio of azoles, bromo alkanol and sodium hydride is 10:10:12.5.
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| CN107502341B (en) * | 2017-08-11 | 2019-10-18 | 江苏第二师范学院 | Piezoluminescence material crystals and preparation method and application |
| CN114957095B (en) * | 2022-06-30 | 2023-06-23 | 江西科技师范大学 | Carbazole derivative and preparation method and application thereof |
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