CN110938017A - Organic molecular material with long afterglow effect based on benzene ring unit and preparation method thereof - Google Patents
Organic molecular material with long afterglow effect based on benzene ring unit and preparation method thereof Download PDFInfo
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- 230000000694 effects Effects 0.000 title claims abstract description 23
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- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 16
- 239000011368 organic material Substances 0.000 claims abstract description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 33
- 238000006243 chemical reaction Methods 0.000 claims description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 19
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 claims description 10
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- 238000004440 column chromatography Methods 0.000 claims description 8
- YWDUZLFWHVQCHY-UHFFFAOYSA-N 1,3,5-tribromobenzene Chemical compound BrC1=CC(Br)=CC(Br)=C1 YWDUZLFWHVQCHY-UHFFFAOYSA-N 0.000 claims description 7
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L magnesium sulphate Substances [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/50—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
- C07C255/51—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings containing at least two cyano groups bound to the carbon skeleton
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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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- C—CHEMISTRY; METALLURGY
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Abstract
The invention discloses an organic molecular material with long afterglow effect based on benzene ring unit and a preparation method thereof, wherein the structural formula of the organic material is as follows:
wherein Y is1、Y2、Y3、Y4Respectively is one or two of hydrogen atom and cyano. By introducing different numbers of cyano groups as electron-withdrawing groups into different sites, the material has the advantages of high synthesis yield, small molecules, continuous luminescence of several seconds after an excitation source is closed, and high fluorescence quantum efficiency. The material has wide potential application value in the fields of anti-counterfeiting, biological imaging, photoelectric materials and the like.
Description
Technical Field
The invention relates to an organic molecular material with a long afterglow effect based on a benzene ring unit and a preparation method thereof, which can be used in the technical field of organic afterglow luminescent materials.
Background
The research of organic ultra-long room temperature phosphorescence (OURTP) draws great attention in various potential applications of optoelectronics and bioscience and in the aspect of expanding the basic understanding of organic light-emitting materials, and provides important guidance for the research of organic optoelectronic materials related to triplet states. In the efforts of scientists, various design strategies have been proposed to develop high performance OURTP molecules with high photoluminescence quantum efficiency (PLQY) and long emission lifetime, including the introduction of aromatic aldehyde, carbonyl or heavy halogens to increase spin-orbit coupling (SOC) for efficient intersystem crossing (ISC) and the suppression of non-radiative transitions of excited states using crystalline, rigid matrices, efficient intermolecular interactions or deuterated carbons.
However, rapid intersystem crossing and strong spin-orbit coupling, which are crucial for the reality of OURTP, cannot be achieved simultaneously by the same strategy at present, so that development of an afterglow material having both a high intersystem crossing rate and strong orbital spin coupling is a very important and urgently needed problem.
Disclosure of Invention
The invention aims to solve the problems in the prior art and provides an organic molecular material based on a benzene ring unit and having a long afterglow effect and a preparation method thereof.
The purpose of the invention is realized by the following technical scheme: an organic molecular material based on a benzene ring unit and having a long afterglow effect has a structural formula as follows:
wherein Y is1、Y2、Y3、Y4Respectively is one or two of hydrogen atom and cyano.
Preferably, the organic material is specifically of the following structural formula:
preferably, said Y is1Is cyano, Y2、Y3、Y4Is hydrogen atom to obtain organic residueA glow material.
Preferably, said Y is2Is cyano, Y1、Y3、Y4Is hydrogen atom, and finally the organic afterglow material is obtained.
Preferably, said Y is3Is cyano, Y1、Y2、Y4Is hydrogen atom, and finally the organic afterglow material is obtained.
Preferably, said Y is2、Y4Is cyano, Y1、Y3Is hydrogen atom, and finally the organic afterglow material is obtained.
The invention discloses a preparation method of an organic molecular material with a long afterglow effect based on a benzene ring unit, which comprises the following steps:
s1: weighing 1, 3, 5-tribromobenzene and cuprous cyanide in a single-mouth bottle under the protection of nitrogen, adding anhydrous N, N-dimethylformamide, stirring and dissolving to obtain a reaction system;
s2: and under the protection of nitrogen, heating the reaction system obtained in the step S1 to reflux for reaction for 10-100 hours, and purifying by column chromatography after extraction to obtain the organic material based on the benzene ring unit and having the long afterglow effect.
Preferably, in the step S1, the molar ratio of the 1, 3, 5-tribromobenzene to the cuprous cyanide is 1: 3-3.5, the reaction temperature is 100-200 ℃, and the reaction time is 10-100 hours.
Preferably, in the S1 step, the reaction temperature is 180 ℃ and the reaction time is 48 hours.
Preferably, in the step S2, the reaction system obtained in the step S1 is heated to reflux under the protection of nitrogen gas, and the reaction is carried out for 48 hours.
Compared with the prior art, the invention adopting the technical scheme has the following technical effects: the material has the advantages of high synthesis yield, small molecules, continuous luminescence of several seconds after an excitation source is closed, and high fluorescence quantum efficiency. The material has wide potential application value in the fields of anti-counterfeiting, biological imaging, photoelectric materials and the like.
Drawings
Fig. 1 is a transient photoluminescence decay spectrum of four target products of the invention.
FIG. 2 is a graph showing the afterglow decay curves of the target product 1 of the present invention.
FIG. 3 is a graph showing the afterglow decay curve of the target product 2 of the present invention.
FIG. 4 is a graph showing the afterglow decay curve of the target product 3 of the present invention.
FIG. 5 is a graph showing the afterglow decay curve of the target product 4 of the present invention.
FIG. 6 is a comparison of four target products of the present invention before and after turning off the UV lamp.
Detailed Description
Objects, advantages and features of the present invention will be illustrated and explained by the following non-limiting description of preferred embodiments. The embodiments are merely exemplary for applying the technical solutions of the present invention, and any technical solution formed by replacing or converting the equivalent thereof falls within the scope of the present invention claimed.
The invention discloses an organic molecular material with a long afterglow effect based on a benzene ring unit, which has the following structural formula:
wherein Y is1、Y2、Y3、Y4Respectively is one or two of hydrogen atom and cyano.
The organic molecular material is specifically represented by the following structural formula:
when Y is1Is cyano, Y2、Y3、Y4Is hydrogen atom to finally obtain the organic afterglow material, the following is1H nuclear magnetic resonance spectrum, chemical shifts in ppm:1H NMR(400MHz，CDCl3，ppm)：δ＝7.88-7.84(m，2H)，7.82-7.78(m，2H)。
when Y is2Is cyano, Y1、Y3、Y4Is hydrogen atom to finally obtain the organic afterglow material, the following is1H nuclear magnetic resonance spectrum, chemical shifts in ppm:1H NMR(400MHz，CDCl3，ppm)：δ＝7.98-7.91(m，3H)，7.70-7.66(m，1H)。
when Y is3Is cyano, Y1、Y2、Y4Is hydrogen atom to finally obtain the organic afterglow material, the following is1H nuclear magnetic resonance spectrum, chemical shifts in ppm:1H NMR(400MHz，CDCl3，ppm)：δ＝ 7.82(s，4H)。
when Y is2、Y4Is cyano, Y1、Y3Is hydrogen atom to finally obtain the organic afterglow material, the following is1H nuclear magnetic resonance spectrum, chemical shifts in ppm:1H NMR(400MHz，CDCl3，ppm)：δ＝8.20 (s，3H)。
the invention also discloses a preparation method of the organic molecular material with the long afterglow effect based on the benzene ring unit, which comprises the following steps:
s1: weighing 1, 3, 5-tribromobenzene and cuprous cyanide in a single-mouth bottle under the protection of nitrogen, adding anhydrous N, N-dimethylformamide, stirring and dissolving to obtain a reaction system;
s2: and under the protection of nitrogen, heating the reaction system obtained in the step S1 to reflux for reaction for a certain time, extracting, and purifying by column chromatography to obtain the organic material based on the benzene ring unit and having the long afterglow effect.
In the step S1, the molar ratio of 1, 3, 5-tribromobenzene to cuprous cyanide is 1: 3-3.5, the reaction temperature is 100-. In the present embodiment, the reaction temperature is preferably 180 ℃ and the reaction time is preferably 48 hours.
Under the protection of nitrogen, heating the reaction system obtained in the step S1 to reflux for reaction for 10-100 hours, and in the technical scheme, in the step S2, heating the reaction system obtained in the step S1 to reflux for reaction for 48 hours under the protection of nitrogen.
In the step of S2, extraction is performed with dichloromethane and water, and column chromatography is performed. In the step S2, dichloromethane and petroleum ether are used as eluent in a volume ratio of 1: 4.
Example 1:
synthesis of target product 1:
s11: to a 250mL round bottom flask equipped with a stir bar were added 1, 4-dibromobenzene (1.17g, 5.0mmol), copper cyanide (4.50g, 50.0mmol), and 50mL dry N, N-dimethylformamide.
S22: the mixture was reacted at 180 ℃ for 48 hours under an argon blanket.
After cooling to room temperature, the solvent of N, N-dimethylformamide was removed by vacuum distillation, the resulting solid was dissolved in DCM and washed with brine, and the mixture was extracted three times with DCM. The organic phase was collected and MgSO4And (5) drying. After removal of the solvent, the crude product was purified by column chromatography and recrystallized several times with DCM/hexane to give the product.1H NMR(400MHz，CDCl3，ppm)：δ＝7.88-7.84(m，2H)， 7.82-7.78(m，2H)。
Example 2:
synthesis of target product 2:
s21: to a 250mL round bottom flask equipped with a stir bar were added 1, 3-dibromobenzene (1.17g, 5.0mmol), copper cyanide (4.50g, 50.0mmol), and 50mL dry N, N-dimethylformamide.
S22: the mixture was reacted at 180 ℃ for 48 hours under an argon blanket.
After cooling to room temperature, the solvent of N, N-dimethylformamide was removed by vacuum distillation. The resulting solid was dissolved in DCM and washed with brine, and the mixture was extracted three times with DCM. The organic phase was collected and MgSO4After drying and removal of the solvent, the crude product was purified by column chromatography and recrystallized several times with DCM/hexane to give the product.1H NMR(400MHz，CDCl3，ppm)：δ＝7.98-7.91(m，3H)， 7.70-7.66(m，1H)。
Example 3:
synthesis of target product 3:
s31: to a 250mL round bottom flask equipped with a stir bar were added 1, 2-dibromobenzene (1.17g, 5.0mmol), copper cyanide (4.50g, 50.0mmol) and 50mL dry N, N-dimethylformamide.
S32: the mixture was reacted at 180 ℃ for 48 hours under an argon blanket.
After cooling to room temperature, the solvent of N, N-dimethylformamide was removed by vacuum distillation. The resulting solid was dissolved in DCM and washed with brine, and the mixture was extracted three times with DCM. The organic phase was collected and MgSO4And (5) drying. After removal of the solvent, the crude product was purified by column chromatography and recrystallized several times with DCM/hexane to give the product.1H NMR(400MHz，CDCl3，ppm)：δ＝7.82(s，4H)。
Example 4:
synthesis of target product 4:
s41: to a 250mL round bottom flask equipped with a stir bar were added 1, 3, 5-tribromobenzene (1.56g, 5.0mmol), copper cyanide (6.75g, 75.0mmol) and 50mL dry N, N-dimethylformamide.
S42: the mixture was reacted at 180 ℃ for 48 hours under an argon blanket.
After cooling to room temperature, the solvent of N, N-dimethylformamide was removed by vacuum distillation. The resulting solid was dissolved in DCM and washed with brine, and the mixture was extracted three times with DCM. The organic phase was collected and MgSO4And (5) drying. After removal of the solvent, the crude product was purified by column chromatography and recrystallized several times with DCM/hexane to give the product.1H NMR(400MHz，CDCl3，ppm)：δ＝8.20(s，3H)。
And (3) testing afterglow emission of target products, and measuring transient photoluminescence attenuation spectrograms of the four target products by using an Edinburgh FLS980 steady-state/transient fluorescence spectrometer, wherein the excitation wavelength is 280nm, the afterglow color of the material is obvious yellow, the spectrogram is shown in figure 1, the ordinate in figure 1 represents time, and the abscissa represents wavelength.
The afterglow life of oCNPh is tested, and the afterglow life decay curves of oCNPh at 403nm and 502nm are measured by using an Edinburgh FLS980 steady-state/transient fluorescence spectrometer, wherein the lifetimes are 69ms and 154ms respectively, the excitation wavelength is 290nm, as shown in FIG. 2, the ordinate represents the intensity and the abscissa represents the time in FIG. 2.
The afterglow life of the mCNph is tested, and the afterglow life decay curves of the mCNph at 470nm and 499nm are measured by using an Edinburgh FLS980 steady-state/transient fluorescence spectrometer, wherein the service lives are 153ms and 164ms respectively, the excitation wavelength is 290nm, as shown in figure 3, the ordinate represents the intensity and the abscissa represents the time in figure 3.
The afterglow life of pCNPh is tested, and afterglow life decay curves of pCNPh at 506nm and 548nm are measured by using an Edinburgh FLS980 steady-state/transient fluorescence spectrometer, wherein the lifetimes are respectively 70ms and 136ms, the excitation wavelength is 290nm, as shown in FIG. 4, the ordinate represents the intensity and the abscissa represents the time in FIG. 4.
The afterglow life of TCNPh is tested, and the afterglow life decay curves of TCNPh at 514nm and 549nm are tested by using an Edinburgh FLS980 steady-state/transient fluorescence spectrometer, wherein the service lives are 506ms and 485ms respectively, the excitation wavelength is 290nm, as shown in FIG. 5, the ordinate represents the intensity and the abscissa represents the time in FIG. 5.
The target products are applied to the anti-counterfeiting aspect, and the four prepared target products can be applied to the anti-counterfeiting aspect. As shown in fig. 6. Four target products obtained by recrystallization generate obvious blue light emission under the irradiation of an ultraviolet lamp of 365nm, the ultraviolet lamp is turned off, obvious yellow light can be observed, the yellow light display time is about 3 seconds, and the anti-counterfeiting of information can be realized based on the method.
The material has the advantages of high synthesis yield, small molecule, continuous luminescence of several seconds after an excitation source is closed, and high fluorescence quantum efficiency.
The technical scheme combines a benzene ring unit and a cyano unit, simultaneously meets the requirements of high intersystem crossing rate and spin-orbit coupling action of the organic long afterglow material by a very simple molecular structure, and the luminescent life of the obtained organic long afterglow molecule reaches 0.5 second, and the time is more than 5 seconds.
The C ≡ N structure in the molecule of the technical scheme can be excitedGenerating n-pi*The invention provides an important clue for researching triplet state generation and long afterglow luminescence phenomena of a solid organic material, and the material has wide potential application values in the fields of anti-counterfeiting, biological imaging, photodynamic therapy, photoelectric materials and the like.
The invention has various embodiments, and all technical solutions formed by adopting equivalent transformation or equivalent transformation are within the protection scope of the invention.
Claims (10)
1. An organic molecular material with long afterglow effect based on benzene ring unit is characterized in that: the structural formula of the organic molecular material is shown as follows:
wherein Y is1、Y2、Y3、Y4Respectively is one or two of hydrogen atom and cyano.
2. The organic molecular material with long afterglow effect based on benzene ring unit as claimed in claim 1, wherein:
the organic molecular material is specifically represented by the following structural formula:
3. the organic molecular material with long afterglow effect based on benzene ring unit as claimed in claim 1, wherein: said Y is1Is cyano, Y2、Y3、Y4Is hydrogen atom, and finally the organic afterglow material is obtained.
4. The method of claim 1An organic molecular material with long afterglow effect based on benzene ring unit is characterized in that: said Y is2Is cyano, Y1、Y2、Y4Is hydrogen atom, and finally the organic afterglow material is obtained.
5. The organic molecular material with long afterglow effect based on benzene ring unit as claimed in claim 1, wherein: said Y is3Is cyano, Y1、Y2、Y4Is hydrogen atom, and finally the organic afterglow material is obtained.
6. The organic molecular material with long afterglow effect based on benzene ring unit as claimed in claim 1, wherein: said Y is2、Y4Is cyano, Y1、Y3Is hydrogen atom, and finally the organic afterglow material is obtained.
7. A preparation method of an organic molecular material with a long afterglow effect based on a benzene ring unit is characterized by comprising the following steps: the method comprises the following steps:
s1: weighing 1, 3, 5-tribromobenzene and cuprous cyanide in a single-mouth bottle under the protection of nitrogen, adding anhydrous N, N-dimethylformamide, stirring and dissolving to obtain a reaction system;
s2: and under the protection of nitrogen, heating the reaction system obtained in the step S1 to reflux for reaction for 10-100 hours, and purifying by column chromatography after extraction to obtain the organic material based on the benzene ring unit and having the long afterglow effect.
8. The method for preparing the organic molecular material with the long afterglow effect based on the benzene ring unit as claimed in claim 7, wherein: in the step S1, the molar ratio of 1, 3, 5-tribromobenzene to cuprous cyanide is 1: 3-3.5, the reaction temperature is 100-.
9. The method for preparing the organic molecular material with the long afterglow effect based on the benzene ring unit as claimed in claim 7, wherein: in the step S1, the reaction temperature was 180 ℃ and the reaction time was 48 hours.
10. The method for preparing the organic molecular material with the long afterglow effect based on the benzene ring unit as claimed in claim 7, wherein: in the step S2, the reaction system obtained in the step S1 was heated to reflux under nitrogen protection to perform the reaction for 48 hours.
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| 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 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102190797A (en) * | 2010-03-08 | 2011-09-21 | 安徽大学 | Quick synthesizing method of triazinyl covalent bond organic framework material with nano pores and application thereof |
| CN103996861A (en) * | 2014-06-05 | 2014-08-20 | 国家纳米科学中心 | Application of polymer product obtained by polymerizing aromaticnitrile compound as oxygen reduction catalyst |
| CN105001032A (en) * | 2014-04-16 | 2015-10-28 | 中国石化扬子石油化工有限公司 | Manufacturing method for nitrile and corresponding amine thereof |
| TW201923029A (en) * | 2017-10-02 | 2019-06-16 | 國立大學法人九州大學 | Organic luminescent composition and luminescent element |
-
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102190797A (en) * | 2010-03-08 | 2011-09-21 | 安徽大学 | Quick synthesizing method of triazinyl covalent bond organic framework material with nano pores and application thereof |
| CN105001032A (en) * | 2014-04-16 | 2015-10-28 | 中国石化扬子石油化工有限公司 | Manufacturing method for nitrile and corresponding amine thereof |
| CN103996861A (en) * | 2014-06-05 | 2014-08-20 | 国家纳米科学中心 | Application of polymer product obtained by polymerizing aromaticnitrile compound as oxygen reduction catalyst |
| TW201923029A (en) * | 2017-10-02 | 2019-06-16 | 國立大學法人九州大學 | Organic luminescent composition and luminescent element |
Non-Patent Citations (2)
| Title |
|---|
| LIANGZHEN CAI 等: "Synthetic Communications: An International Journal for Rapid Communication of Synthetic Organic Chemistry", 《SYNTHETIC COMMUNICATIONS》 * |
| TAKEHIKO ITO 等: "Studies of Organic Catalytic Reactions. VI. The Function of Pyridine and Copper in the Rosenmund-von Braun Reaction", 《BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
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