CN106883163A - A kind of organic compound with long afterglow effect and its preparation method and application - Google Patents
A kind of organic compound with long afterglow effect and its preparation method and application Download PDFInfo
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- CN106883163A CN106883163A CN201710099367.7A CN201710099367A CN106883163A CN 106883163 A CN106883163 A CN 106883163A CN 201710099367 A CN201710099367 A CN 201710099367A CN 106883163 A CN106883163 A CN 106883163A
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- 0 *c(c(*)c1*)c(*)c(*)c1-[n]1c2ccccc2c2c1cccc2 Chemical compound *c(c(*)c1*)c(*)c(*)c1-[n]1c2ccccc2c2c1cccc2 0.000 description 1
- UJOBWOGCFQCDNV-UHFFFAOYSA-N c(cc1)cc2c1[nH]c1c2cccc1 Chemical compound c(cc1)cc2c1[nH]c1c2cccc1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 1
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- C07D—HETEROCYCLIC COMPOUNDS
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- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
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- C09K2211/1007—Non-condensed systems
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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Abstract
The invention discloses a kind of organic compound with long afterglow effect and its preparation method and application, the structural formula of the organic compound is：Unit based on 9 phenyl carbazoles with n π * transition is chosen, is modified in the meta of phenyl and contraposition, 9 different phenyl carbazole derivatives are obtained after modification；After tested, the luminescent lifetime of this kind of compound can reach more than 100ms.Such compound has synthetic method simple, is easily purified, and luminescent spectrum is adjustable, flexible, and cheap without the inorganic rare earth material that adulterates, the low feature of toxicity can be widely used in the every field such as bio-imaging, medical diagnosis on disease, optical anti-counterfeiting.
Description
Technical field
The invention belongs to organic afterglow materials technical field, and in particular to a kind of 9- phenyl carbazoles with n- π * transition
Based on unit there is organic compound of long afterglow effect and its preparation method and application.
Background technology
Long after glow luminous material abbreviation long-afterglow material, the light-storing and emitting material that is otherwise known as, Noctilucent material, it is substantially
Be a kind of embedded photoluminescent material, be a class energy absorption such as visible ray, ultraviolet light, X-ray etc., and excite stop after still can be after
The material of supervention light extraction, can store energy in falling into, and have broad application prospects.
Inorganic long-afterglow material is one of research and the earliest material of application, and many natural crystals inherently have long afterglow
The characteristics of luminescence, and for making various articles, such as " luminous wine glass ", " legendary luminous pearl ".The inorganic afterglowing material of tradition has various lacking
Point：1) synthesis condition is harsh, and condition is numerous and diverse；2) the inorganic rare earth material that adulterates generally is needed, price is high, and toxicity is big；3) and need
Grinding is used, it is difficult to using on flexible substrates.
The content of the invention
The technical problem of solution：The purpose of the present invention is to overcome existing inorganic afterglowing material synthesis condition harsh, numerous and diverse, is needed
Adulterate inorganic rare earth material, the defect that price is high, toxicity is big, there is provided a kind of based on the 9- phenyl carbazoles of n- π * transition
Organic compound with long afterglow effect of unit and its preparation method and application.Organic long-persistence luminous compound has
Synthetic method is simple, and luminescent spectrum is adjustable, and flexible, cheap without the inorganic rare earth material that adulterates, the low feature of toxicity can
It is widely used in multi-level encryption false proof (glow color, life-span etc.), each field of the photoelectronics such as medical diagnosis on disease and bio-imaging.
Technical scheme：A kind of organic compound with long afterglow effect, be using the 9- phenyl carbazoles of n- π * transition as
Base unit, its structural formula is as follows：
Wherein, X0、X1、X2、X3、X4Selected from hydrogen, halogen atom, alkyl, alkoxy, amino, cyano group, carboxyl or carbazole, can
With identical or different.
The preparation method of the above-mentioned organic compound with long afterglow effect, is by 1 times of equivalent carbazole, 1~1.5 times of equivalent
Halogeno-benzene or halo benzene derivative, 0.44 times of equivalent Cu, the K of 4.04 times of equivalents2CO3Be put into reaction vessel, using nitrobenzene as
Reaction dissolvent, lower 120~160 DEG C of 12~48h of reaction of nitrogen protection, reaction solution obtains crude product by vacuum distillation, through column chromatography
Obtain clean product.
Application of the above-mentioned organic compound with long afterglow effect in Multi-stage antiforging field of encryption.
Application of the above-mentioned organic compound with long afterglow effect in diagnosis developer is prepared.
Application of the above-mentioned organic compound with long afterglow effect in bio-imaging field.
Application of the above-mentioned organic compound with long afterglow effect in anti-counterfeiting mark is prepared.
Beneficial effect：There are organic compound with long afterglow effect of the invention reaction raw materials to be easy to get, reaction condition
Simply, it is nontoxic, be to realize that multi-level encryption is false proof (glow color, life-span etc.) the advantages of prepare convenient, flexible, medical diagnosis on disease and
The ideal product of bio-imaging etc..
Brief description of the drawings
Fig. 1 is the stable state and transient state spectrum spectrogram of the gained compound of embodiment 1 to 5, and illustration is respective compound in 365nm
Pictorial diagram (left figure) under exciting and take off the sunset glow figure (right figure) after exciting；
Fig. 2 is the crystallo-luminescence life diagram of the gained compound of embodiment 1 to 5, and a is the gained crystal of embodiment 1, b to implement
The gained crystal of example 2, c are the gained crystal of embodiment 3, d is the gained crystal of embodiment 4, e is the gained crystal of embodiment 5；
Fig. 3 is that the device of the gained compound crystal of embodiment 1 to 5 prepares schematic diagram；
Fig. 4 is the device twilight sunset design sketch of the gained compound crystal of embodiment 1.
Specific embodiment
Specific embodiment of the invention is described in detail below, it should be appreciated that described herein specific
Implementation method is merely to illustrate and explain the present invention, and is not intended to limit the invention.
The invention provides a kind of organic compound with long afterglow effect, made with the 9- phenyl carbazoles of n- π * transition
Based on unit, its structural formula is as follows：
Wherein, X0、X1、X2、X3、X4Selected from hydrogen, halogen atom, alkyl, alkoxy, amino, cyano group, carboxyl or carbazole, can
With identical or different.
The present invention stablizes the triplet state in organic photoelectrical material by being introduced into special accumulation mode in organic molecule
Exciton, then again slowly discharges the triplet excited states exciton of stabilization, so as to improve the luminescent lifetime of material.It is this kind of
Material usually contains the N atoms with n- π * transition, its can promote singlet excited state to triplet excited states be between alter
More, so as to produce triplet excited states exciton.Each plane substituted radical promotes intermolecular formation H- aggregations falling into as energy
Trap, so as to stablize triplet excited states exciton, then slow release again, so as to realize the long-life of pure organic photoelectric functional material
It is luminous.
Specifically, the present invention choose with n- π * transition 9- phenyl carbazoles based on unit, the ortho position of phenyl,
Position and contraposition are modified, and various different 9- phenyl carbazole derivatives are obtained after modification.After tested, the highest of this kind of compound
Luminescent lifetime can reach 330ms.Such compound has synthetic method simple, and luminescent spectrum is adjustable, flexible, without nothing of adulterating
Machine rare earth material, cheap, the low feature of toxicity, can by extensively should false proof (glow color, life-span etc.) with multi-level encryption,
Each field of the photoelectronics such as medical diagnosis on disease and bio-imaging.
Embodiment 1
PhCz synthesizes：First, by 1 times of carbazole of equivalent, 1~1.5 times of equivalents of halogen benzene, such as bromobenzene, fluorobenzene,
0.44 times of equivalent Cu (electrolytical refined copper), 4.04 times of K of equivalent2CO3It is put into reaction vessel, using nitrobenzene as reaction dissolvent,
Lower 120~160 DEG C of 12~48h of reaction of nitrogen protection, reaction solution obtains 9- phenyl carbazole crude products by vacuum distillation, by post layer
Analysis obtains clean product, yield 85~95%.
Its hydrogen is composed1H NMR(400MHz,CDCl3),δ(TMS,ppm):8.21(d,2H),7.66(m,4H),7.52(m,
5H),7.34(m,2H)。
Fig. 1 is the stable state and transient state spectrum spectrogram of gained compound, and excitation wavelength is 295nm, transient state spectrum time delay
It is 10ms.Illustration is pictorial diagram (left figure) of the respective compound in the case where 365nm is excited and takes off the sunset glow figure (right figure) after exciting.
It is prepared by device：The clean product of gained is spin-dried for, is filtered with dichloromethane ultrasonic dissolution, added in filtrate bad
Solvent, stirs, static slow volatilization, is filtrated to get required compound crystal, and gained compound crystal is sent out
Optical tests, as a result as shown in Figure 2.Go out information one in the front print of flexible transparent substrate, i.e., southern postal logo, then flexible saturating
The reverse side of bright substrate prints Blue fluorescent ink entirely, finally, Freehandhand-drawing after being ground with gained compound crystal in underlying substrate
Or printing information two, i.e. IAM team logo.Device preparation principle figure is as shown in Figure 3；Obtained device twilight sunset design sketch such as Fig. 4 institutes
Show.
Embodiment 2
PBrPhCz synthesizes：First, by 1 times of carbazole of equivalent, 1~1.5 times of equivalent to phenyl-dihalide, such as paradibromobenzene,
0.44 times of equivalent Cu (electrolytical refined copper), 4.04 times of K of equivalent2CO3It is put into reaction vessel, using nitrobenzene as reaction dissolvent,
Lower 120~160 DEG C of 12~48h of reaction of nitrogen protection, reaction solution obtains crude product, obtains pure by column chromatography by vacuum distillation
Product, yield 75~85%.
Its hydrogen is composed1H NMR(400MHz,CDCl3),δ(TMS,ppm):8.16(d,2H),7.75(d,2H),7.47(m,
6H),7.34(t,2H)。
Fig. 1 is the stable state and transient state spectrum spectrogram of gained compound, and excitation wavelength is 295nm, transient state spectrum time delay
It is 10ms.Illustration is pictorial diagram (left figure) of the respective compound in the case where 365nm is excited and takes off the sunset glow figure (right figure) after exciting.
The clean product of gained is spin-dried for, is filtered with dichloromethane ultrasonic dissolution, poor solvent is added in filtrate, fully
Stir, static slow volatilization is filtrated to get required compound crystal, gained compound crystal is carried out into luminous test, knot
Fruit is as shown in Figure 2.
Embodiment 3
MBrPhCz synthesizes：First, by 1 times of carbazole of equivalent, phenyl-dihalide, such as m-dibromobenzene between 1~1.5 times of equivalent,
0.44 times of equivalent Cu (electrolytical refined copper), 4.04 times of K of equivalent2CO3It is put into reaction vessel, using nitrobenzene as reaction dissolvent,
Lower 120~160 DEG C of 12~48h of reaction of nitrogen protection, reaction solution obtains crude product, obtains pure by column chromatography by vacuum distillation
Product, yield 75~85%.
Its hydrogen is composed1H NMR(400MHz,CDCl3),δ(TMS,ppm):8.30(d,2H),7.90(s,1H),7.71(d,
1H),7.62(m,8H)。
Fig. 1 is the stable state and transient state spectrum spectrogram of gained compound, and excitation wavelength is 295nm, transient state spectrum time delay
It is 10ms.Illustration is pictorial diagram (left figure) of the respective compound in the case where 365nm is excited and takes off the sunset glow figure (right figure) after exciting.
The clean product of gained is spin-dried for, is filtered with dichloromethane ultrasonic dissolution, poor solvent is added in filtrate, fully
Stir, static slow volatilization is filtrated to get required compound crystal, gained compound crystal is carried out into luminous test, knot
Fruit is as shown in Figure 2.
Embodiment 4
DBrPhCz synthesizes：First, by 1 times of carbazole of equivalent, 1~1.5 times of equal phenyl trihalide of equivalent, such as 1,3,5- tribromos
Benzene etc., 0.44 times of equivalent Cu (electrolytical refined copper), 4.04 times of K of equivalent2CO3It is put into reaction vessel, using nitrobenzene as reaction
Solvent, lower 120~160 DEG C of 12~48h of reaction of nitrogen protection, reaction solution is obtained crude product, is obtained by column chromatography by vacuum distillation
To clean product, yield 50~65%.
Its hydrogen is composed1H NMR(400MHz,CDCl3),δ(TMS,ppm):8.14(d,2H),7.77(s,1H),7.71(s,
1H),7.47(m,4H),7.34(m,2H)。
Fig. 1 is the stable state and transient state spectrum spectrogram of gained compound, and excitation wavelength is 295nm, transient state spectrum time delay
It is 10ms.Illustration is pictorial diagram (left figure) of the respective compound in the case where 365nm is excited and takes off the sunset glow figure (right figure) after exciting.
The clean product of gained is spin-dried for, is filtered with dichloromethane ultrasonic dissolution, poor solvent is added in filtrate, fully
Stir, static slow volatilization is filtrated to get required compound crystal, gained compound crystal is carried out into luminous test, knot
Fruit is as shown in Figure 2.
Embodiment 5
PCNPhCz synthesizes：First, by 1 times of carbazole of equivalent, 1~1.5 times of equivalents of halogen benzene cyanogen, such as to bromobenzene cyanogen,
0.44 times of equivalent Cu (electrolytical refined copper), 4.04 times of K of equivalent2CO3It is put into reaction vessel, using nitrobenzene as reaction dissolvent,
Lower 120~160 DEG C of 12~48h of reaction of nitrogen protection, reaction solution obtains crude product, obtains pure by column chromatography by vacuum distillation
Product, yield 80~85%.
Its hydrogen is composed1H NMR(400MHz,CDCl3),δ(TMS,ppm):8.16(d,2H),7.91(d,2H),7.75(d,
2H),7.48(m,4H),7.37(m,2H)。
Fig. 1 is the stable state and transient state spectrum spectrogram of gained compound, and excitation wavelength is 295nm, transient state spectrum time delay
It is 10ms.Illustration is pictorial diagram (left figure) of the respective compound in the case where 365nm is excited and takes off the sunset glow figure (right figure) after exciting.
The clean product of gained is spin-dried for, is filtered with dichloromethane ultrasonic dissolution, poor solvent is added in filtrate, fully
Stir, static slow volatilization is filtrated to get required compound crystal, gained compound crystal is carried out into luminous test, knot
Fruit is as shown in Figure 2.
The characteristics of luminescence and performance parameter of the gained compound crystal of embodiment 1 to 5 are as shown in the table：
As seen from the above table, synthesized compound has the room temperature phosphorimetry life-span very long, wherein the compound after modification
1,2,3 and 5 luminescent lifetime has reached more than 100ms, while afterglow luminescence spectrum covers the scope of 450~750nm.
Claims (6)
1. a kind of organic compound with long afterglow effect, it is characterised in that：Using the 9- phenyl carbazoles of n- π * transition as base
Plinth unit, its structural formula is as follows：
Wherein, X0、X1、X2、X3、X4Selected from hydrogen, halogen atom, alkyl, alkoxy, amino, cyano group, carboxyl or carbazole, Ke Yixiang
It is same or different.
2. the preparation method of the organic compound with long afterglow effect described in claim 1, it is characterised in that：1 times is worked as
Amount carbazole, 1~1.5 times of equivalents of halogen benzene or halo benzene derivative, 0.44 times of equivalent Cu, the K of 4.04 times of equivalents2CO3It is put into reaction
In container, using nitrobenzene as reaction dissolvent, lower 120~160 DEG C of 12~48h of reaction of nitrogen protection, reaction solution is steamed by depressurizing
Evaporate and obtain crude product, clean product is obtained through column chromatography.
3. application of the organic compound with long afterglow effect described in claim 1 in Multi-stage antiforging field of encryption.
4. application of the organic compound with long afterglow effect described in claim 1 in bio-imaging field.
5. application of the organic compound with long afterglow effect described in claim 1 in diagnosis developer is prepared.
6. application of the organic compound with long afterglow effect described in claim 1 in anti-counterfeiting mark is prepared.
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Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109761991A (en) * | 2019-02-28 | 2019-05-17 | 南京邮电大学 | Material, Preparation method and use with long-life room temperature phosphorimetry phenomenon |
| CN110272379A (en) * | 2019-07-12 | 2019-09-24 | 福州大学 | A kind of synthesis and its Application in Anti-counterfeiting of halogen atom-containing room temperature phosphorimetry material |
| CN110423244A (en) * | 2019-08-06 | 2019-11-08 | 南京邮电大学 | A kind of preparation and its application of the organic boron phosphor material with overlength afterglow luminescent properties |
| WO2020199191A1 (en) * | 2019-04-04 | 2020-10-08 | 复旦大学 | Long-lasting phosphor material |
| CN111777543A (en) * | 2020-07-15 | 2020-10-16 | 中钢集团南京新材料研究院有限公司 | Method for preparing N-phenylcarbazole through copper-catalyzed bromobenzene and carbazole C-N coupling |
| US20200348178A1 (en) * | 2018-01-23 | 2020-11-05 | Hamamatsu Photonics K.K. | Light measurement device and light measurement method |
| CN111960988A (en) * | 2020-10-21 | 2020-11-20 | 南京工业职业技术大学 | Novel thermal activation delayed fluorescence material based on excimer luminescence and application thereof |
| WO2020252760A1 (en) * | 2019-06-21 | 2020-12-24 | 复旦大学 | Controllable long persistent luminescent material |
| WO2021139092A1 (en) * | 2020-01-09 | 2021-07-15 | 中山大学 | Ligand compound, and functionalized metal-organic framework compound prepared by same, preparation method therefor and application thereof |
| CN115160304A (en) * | 2022-06-16 | 2022-10-11 | 安徽秀朗新材料科技有限公司 | Carbazole derivative production process |
| WO2023173889A1 (en) * | 2022-03-16 | 2023-09-21 | 深圳先进技术研究院 | Up-conversion long-afterglow chemiluminescence imaging nanoprobe, and preparation method therefor and use thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN109761991A (en) * | 2019-02-28 | 2019-05-17 | 南京邮电大学 | Material, Preparation method and use with long-life room temperature phosphorimetry phenomenon |
| WO2020199191A1 (en) * | 2019-04-04 | 2020-10-08 | 复旦大学 | Long-lasting phosphor material |
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| CN110272379A (en) * | 2019-07-12 | 2019-09-24 | 福州大学 | A kind of synthesis and its Application in Anti-counterfeiting of halogen atom-containing room temperature phosphorimetry material |
| CN110423244A (en) * | 2019-08-06 | 2019-11-08 | 南京邮电大学 | A kind of preparation and its application of the organic boron phosphor material with overlength afterglow luminescent properties |
| CN110423244B (en) * | 2019-08-06 | 2022-06-17 | 南京邮电大学 | Preparation and application of organic boron phosphorescent material with ultra-long afterglow luminescence property |
| WO2021139092A1 (en) * | 2020-01-09 | 2021-07-15 | 中山大学 | Ligand compound, and functionalized metal-organic framework compound prepared by same, preparation method therefor and application thereof |
| CN111777543A (en) * | 2020-07-15 | 2020-10-16 | 中钢集团南京新材料研究院有限公司 | Method for preparing N-phenylcarbazole through copper-catalyzed bromobenzene and carbazole C-N coupling |
| CN111960988A (en) * | 2020-10-21 | 2020-11-20 | 南京工业职业技术大学 | Novel thermal activation delayed fluorescence material based on excimer luminescence and application thereof |
| WO2023173889A1 (en) * | 2022-03-16 | 2023-09-21 | 深圳先进技术研究院 | Up-conversion long-afterglow chemiluminescence imaging nanoprobe, and preparation method therefor and use thereof |
| CN115160304A (en) * | 2022-06-16 | 2022-10-11 | 安徽秀朗新材料科技有限公司 | Carbazole derivative production process |
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