CN105001141A - Fluoro phenylindole compound, application of fluoro phenylindole compound as red organic luminescent material, and preparation method of fluoro phenylindole compound - Google Patents
Fluoro phenylindole compound, application of fluoro phenylindole compound as red organic luminescent material, and preparation method of fluoro phenylindole compound Download PDFInfo
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- C07—ORGANIC CHEMISTRY
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- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/12—Radicals substituted by oxygen atoms
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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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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
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- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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Abstract
The invention discloses a fluoro phenylindole compound which adopts a structure shown in formula I, application of the fluoro phenylindole compound as a red organic luminescent material, and a preparation method of the fluoro phenylindole compound. The fluoro phenylindole compound is obtained through a reaction between cyclohexanone and 3-(3-(4-fluorophenyl)-1-isopropyl-1H-indole-2-yl) acrolein under an alkaline condition. The preparation method is simple to operate, convenient for synthesis and easy for purification; the obtained fluoro phenylindole compound is stable in structure and can be utilized for fluorescence conversion on a strong red color displayed under 800-nm laser excitation, thereby having potential application values in such fields as luminescent equipment, anti-counterfeit technologies, laser dye and fluorescence sensing; the research field of the fluoro phenylindole compound is expanded.
Description
Technical field:
The present invention relates to technical field of organic luminescence materials, be specifically related to a kind of difluorophenyl Benzazole compounds, its application as red luminous organic material and preparation method thereof.
Background technology:
Luminous organic material is widely used in multiple fields such as photoelectron, photovoltaic cell, fluorescent optical sensor, and its feature of giving prominence to the most is exactly to be optical radiation by absorbed various forms of energy conversion.Along with the fast development of modern science and technology, the Application Areas of luminous organic material is constantly expanded, in the urgent need to developing efficient, inexpensive, Wavelength tunable, excellent performance luminous organic material, to meet the demand of current field of photoelectric technology.
Upconverting fluorescent material can launch visible ray, even UV-light under long wave (as infrared light) excites, and namely long wave excites, short wavelength emissions.This material is the advantages such as luminosity is stable, bio-toxicity is low, fluorescence signal to noise ratio is high because having, be with a wide range of applications in the field such as optical fiber communication technology, fibre amplifier, 3 D stereo display, biomolecules fluorescence labelling, infrared detective and solar cell, especially in medical diagnosis on disease, imaging biological cells and anti-counterfeiting technology etc., there is even more important realistic meaning.
As one of most important luminescent material, research and development that are red and infrared fluorescent material enjoy the concern of research staff always.This is mainly based on following reason: (1) red emissive material is one of colour and the three primary colours (RGB) needed for white light emitting device; (2) red and infrared fluorescent material has clear superiority in bio-medical analysis, because red and infrared longer-wave photons is not easily by Cell uptake, therefore little to cell phototoxicity, easily penetrate biological tissue, and fluorescence background is low.
Although people have carried out large quantity research in above-mentioned field at present, and achieve greater advance, but still have that kind that is red and infrared light fluorescent material is less, synthesis is complicated and cost is high, efficiency is lower, easily occur that quenching of fluorescence, chemical stability and fluorescent stability are poor, the problems such as background fluorescence serious interference and bio-toxicity height, the demand of current each field development cannot be met, also constrain research and development and the application of some new technologies simultaneously.Therefore, the red and infrared luminous organic material of research and development excellent performance is the very important problem of current photoelectric material and bio-medical analysis area research one, and has broad application prospects.
Cycloalkanones curcumin analogue is the compound that a class has the multiple physiologically active such as antitumor, anti-oxidant, antibacterial, this compounds obtains the larger attention of researchist in recent years, and carried out extensive research, but, these research work are often only limitted to field of medicaments, and few as the research of up-conversion luminescent material.
3-(3-(4-fluorophenyl)-1-sec.-propyl-1H-indoles-2-base) propenal is the important intermediate of synthesis prevention and therapy cardiovascular disease medicine fluvastatin, in prior art, synthetic method, technical study are limited to more to its research, and as the application of medicine intermediate, and few for the preparation of luminescent material.Chinese patent CN104535552A discloses the application in pH fluorescent probe and cell imaging of 3-(3-(4-fluorophenyl)-1-sec.-propyl-1H-indoles-2-base) propenal, the emission wavelength of this compound is 528nm, is green-fluorescent emission.But the compound involved by this invention is only limitted to 3-(3-(4-fluorophenyl)-1-sec.-propyl-1H-indoles-2-base) propenal itself, more attention is the applied research in pH fluorescent probe of this compound, do not relate to this compound and derivative thereof as the research of novel organic luminescent material, particularly do not relate to the content of red up-conversion luminescent material and application.Therefore, still there is many weak points.
At present, with 3-(3-(4-fluorophenyl)-1-sec.-propyl-1H-indoles-2-base) propenal for raw material, by polyene ketone structural unit, two difluorophenyl indoles function bases are connected, thus form two difluorophenyl indoles acrol pimelinketone compound, and investigate the research of the aspects such as its Upconversion luminescence, have no report in the prior art.
Summary of the invention:
The object of this invention is to provide a kind of difluorophenyl Benzazole compounds, its application as red luminous organic material and preparation method thereof.
The present invention is achieved by the following technical programs:
An object of the present invention is the difluorophenyl Benzazole compounds proposed shown in a kind of formula I:
The present invention with 3-(3-(4-fluorophenyl)-1-sec.-propyl-1H-indoles-2-base) propenal for raw material, by polyene ketone structural unit, two difluorophenyl indoles function bases are connected, thus define two difluorophenyl indoles acrol pimelinketone compound.
The synthetic route of difluorophenyl Benzazole compounds of the present invention is as follows:
Another object of the present invention proposes the application of difluorophenyl Benzazole compounds as red luminous organic material, and it can be used for the fields such as luminescent device, anti-fake material, laser dyes, sensitive fluorescent and bio-medical analysis.
Preferably, difluorophenyl Benzazole compounds is as the application of the organic up-conversion luminescent material of redness.
Difluorophenyl Benzazole compounds of the present invention is as the application of luminescent material.In fields such as luminescent device, laser dyes, sensitive fluorescent, anti-counterfeiting technology, 3 D stereo display, bio-medical analysis, there is potential application foreground.
The invention provides a kind of preparation method of difluorophenyl Benzazole compounds, comprise the steps:
Be that pimelinketone (compound III) and 3-(3-(4-the fluorophenyl)-1-sec.-propyl-1H-indoles-2-base) propenal (compound ii) of 1:2 ~ 2.2 is dissolved in organic solvent by mol ratio, stir lower dropping 10 ~ 20 milliliters of alkaline solutions, at room temperature stirring reaction 10 ~ 15 hours, by in reaction solution impouring 150 ml water, gained solid matter decompress filter, wash with water, drying at room temperature.With ethanol-acetone mixing solutions recrystallization, obtain two (3-(3-(4-the fluorophenyl)-1-sec.-propyl-1H-indoles-2-base) acrol) pimelinketone (Compound I) of target compound 3,5-.
The preparation method that the present invention proposes, simple to operate, synthesis is convenient, easy purifying, and the target compound Stability Analysis of Structures obtained is practical.Meanwhile, the up-conversion luminescent material of various different wave length can be obtained by the method for chemically modified, to meet different application demand.The present invention has expanded the investigation and application field of difluorophenyl Benzazole compounds.
Organic solvent described in step a is preferably methyl alcohol or ethanol; Alkaline solution described in step b is preferably the potassium hydroxide aqueous solution of 15 ~ 20%, or the aqueous sodium hydroxide solution of 15 ~ 20%.
Beneficial effect of the present invention is:
(1) the present invention with 3-(3-(4-fluorophenyl)-1-sec.-propyl-1H-indoles-2-base) propenal for raw material, by polyene ketone structural unit, two difluorophenyl indoles function bases are connected, thus define two difluorophenyl indoles acrol pimelinketone compound.With regard to molecular structure, there is the substituted indole group of two electron riches in molecule two ends, mid-molecule is strong electron withdrawing group carbonyl, two parts are connected by polyene structure unit, define a D-π-A-π-D type conjugated system that is larger, that more expand, effective Intramolecular electron transfer can be produced, thus be conducive to strengthening organic materials up-conversion luminescence performance.
(2) existence of three methylene radical of two sec.-propyls and pimelinketone in molecule, can effectively increase the sterically hindered of molecule, reduce the coplanarity of whole molecule to a certain extent, intermolecular interaction when therefore effectively can reduce high density, prevent concentration quenching, promote the raising of luminous efficiency; Meanwhile, the introducing of sec.-propyl can also increase the solubleness of this compounds.
(3) in molecule two there is the introducing of the fluorine atom of strong electronegativity, change physicochemical property and the physiologically active in vivo of this compound largely, the application performance of compound be greatly improved.This is mainly reflected in three aspects:
The first, the formation of strong C-F key, can either strengthen the chemical stability of molecule, can put forward high molecular volatility again, is conducive to the preparation of luminescent device; Second, introduce C-F key in the molecule, the level structure of organic molecule, aggregated structure or packing of molecules form can also be changed, thus cause the change of organic materials photoelectric properties and processing characteristics, and effectively can reduce the concentration quenching of luminescent material, thus reach the object improving luminous efficiency; 3rd, introduce fluorine atom in the molecule and can improve the fat-soluble of this molecule, and make compound have better penetration power to film, tissue etc., improve the absorption of fluorochemicals in organism and transmission speed, thus be conducive to improving the application performance of compound in the bio-medical analysis such as fluorescent probe, bio-imaging.
(4) because difluorophenyl indole structure unit is an important pharmacophoric group, it is the important component part of medicine fluvastatin, therefore, difluorophenyl Benzazole compounds of the present invention has physiologically active and luminescent properties two kinds of characteristics concurrently, relating to multiple fields such as chemistry, optics, biology, medicine and material, is a class novel organic luminescent material.Material of the present invention, except can be used for the fields such as luminescent device, laser dyes, anti-counterfeiting technology, has more actual application value in medicine tracking, pharmaceutical activity and study on mechanism, medical diagnosis etc.
(5) difluorophenyl Benzazole compounds Stability Analysis of Structures of the present invention, be easy to preserve, in dichloromethane solution, show wide band absorption characteristic, present a strong and wide absorption band at 310nm ~ 560nm wave band, absorption peak is positioned at 468nm.This broad band absorbs, and reduces pump light adaptive with the energy of energy inter-stage, reduces the requirement to pump wavelength.Meanwhile, under 800nm laser excitation, launch strong red up-conversion fluorescence, emission peak is positioned at 612nm, shows good red Upconversion luminescence.Exciting light of the present invention is positioned at the 800nm of near-infrared region, and the light loss that effectively prevent high-energy exciting light injures the shortcoming of biological context fluorescence, in bio-medical analysis etc., have larger using value.
Accompanying drawing illustrates:
Fig. 1 is the uv absorption spectra of embodiment 1 compound in dichloromethane solution;
Fig. 2 is the fluorescence emission spectrogram of embodiment 1 compound in dichloromethane solution;
Fig. 3 is the Up-conversion emission spectrogram of embodiment 1 compound in dichloromethane solution;
Fig. 4 is that embodiment 1 compound up-conversion fluorescence intensity is to the dependence of pump laser power.
Embodiment:
Below further illustrate of the present invention, instead of limitation of the present invention.
Laboratory apparatus and model: Bruker AVANCE-300 nuclear magnetic resonance spectrometer; Agilent LC/MSD Trap XCT mass spectrograph; HORIBAJobin Yvon Aqualog absorbs and three-dimensional fluorescence scanning spectrometer; Perkin Elmer LS-55 spectrophotofluorometer; Ti∶Sapphire laser fs-laser system (Coherent company).
The preparation of two (3-(3-(4-the fluorophenyl)-1-sec.-propyl-1H-indoles-2-base) acrol) pimelinketone (I) of embodiment 1:3,5-:
In 250 milliliters of round-bottomed flasks, pimelinketone (1mmol) and 3-(3-(4-fluorophenyl)-1-sec.-propyl-1H-indoles-2-base) propenal (2mmol) are dissolved in 50 milliliters of ethanol or methyl alcohol, 10 milliliter of 15% potassium hydroxide solution is dripped under fast stirring in this solution, and at room temperature stirring reaction 10 ~ 15 hours.Afterwards, by reaction solution impouring 150 ml water, gained solid matter decompress filter, washes with water for several times, drying at room temperature.With ethanol-acetone mixed solvent recrystallization, vacuum-drying, obtains red solid, and productive rate is 68%.
1H NMR(300MHz,CDCl
3/TMS)δ:1.67-1.71(m,14H),2.30(t,J＝5.4Hz,4H),4.86-4.96(m,2H),6.50(d,J＝12.0,15.3Hz,1H),6.55(d,J＝15.3Hz,1H),7.01-7.25(m,10H),7.32-7.43(m,6H),7.49(d,J＝7.8Hz,2H),7.53(d,J＝8.4Hz,2H)；
13C NMR(125MHz,CDCl
3/TMS)δ:21.77,21.91,26.09,47.81,111.71,115.54,115.71,117.73,119.92,120.09,122.95,128.55,128.58,128.76,131.38,131.41,131.93,131.99,133.44,135.47,136.05,136.21,160.91,162.86,188.69；ESI-MS m/z:677.3(M+H)
+。
The preparation of two (3-(3-(4-the fluorophenyl)-1-sec.-propyl-1H-indoles-2-base) acrol) pimelinketone (I) of embodiment 2:3,5-:
In 250 milliliters of round-bottomed flasks, pimelinketone (1mmol) and 3-(3-(4-fluorophenyl)-1-sec.-propyl-1H-indoles-2-base) propenal (2.2mmol) are dissolved in 50 milliliters of ethanol or methyl alcohol, 20 milliliter of 20% sodium hydroxide solution is dripped under fast stirring in this solution, and at room temperature stirring reaction 10 ~ 15 hours.Afterwards, by reaction solution impouring 150 ml water, gained solid matter decompress filter, washes with water for several times, drying at room temperature.With ethanol-acetone mixed solvent recrystallization, vacuum-drying, obtains red solid, and productive rate is 72%.ESI-MS m/z:677.3(M+H)
+。
The fluorescence property test of two (3-(3-(4-the fluorophenyl)-1-sec.-propyl-1H-indoles-2-base) acrol) pimelinketone (I) of embodiment 3:3,5-
It is 2 × 10 that embodiment 1 compound is mixed with concentration
-5mol/L dichloromethane solution.In HORIBA Jobin Yvon Aqualog absorption and three-dimensional fluorescence scanning spectrometer, measure its ultra-violet absorption spectrum with 1 centimetre of fluorescence pond, PerkinElmer LS-55 spectrophotofluorometer measures its fluorescence spectrum, and result as depicted in figs. 1 and 2.
It is 2 × 10 that embodiment 1 compound is mixed with concentration
-4mol/L dichloromethane solution has been the femtosecond Ti:sapphire laser determination of 800nm with the wavelength Upconversion luminescence of embodiment 1 molecule, its up-conversion fluorescence spectrum is shown in Fig. 3.
As shown in Figure 1, embodiment 1 molecule, in dichloromethane solution, shows wide band absorption characteristic, and present a strong and wide absorption band at 310nm ~ 560nm wave band, absorption peak is positioned at 468nm, and is being greater than 560nm wave band without obvious absorption.As shown in Figure 2, the fluorescence emission peak of embodiment 1 molecule is positioned at 575nm, is yellow fluorescence.
Embodiment 1 compound, not only has good yellow fluorescence performance, and under the near-infrared laser of 800nm excites, also presents good up-conversion fluorescence performance.As shown in Figure 3, under 800nm laser excitation, embodiment 1 compound launches strong red up-conversion fluorescence in dichloromethane solution, and its fluorescence emission peak is positioned at 612nm.Up-conversion fluorescence spectrum is compared with above-mentioned linear fluorescence spectrum, and the peak shape of the two is similar, but up-conversion fluorescence emission band is wider, and the 612nm of peak-peak also from the 575nm red shift of linear fluorescence to up-conversion fluorescence.
Further by Up-conversion Intensity to the Study on dependence of pump laser power up-conversion luminescence mechanism, as shown in Figure 4.Along with the increase of excitation light source power, up-conversion fluorescence intensity is in the trend strengthened gradually, fluorescence intensity and exciting power square present good linear relationship (its slope is 1.9036), prove that this red Up-conversion emission comes from biphotonic process, result shows, target compound is a kind of effective red up-conversion luminescent material.
Difluorophenyl Benzazole compounds of the present invention is as the application of luminescent material.All there is potential application foreground in fields such as luminescent device, laser dyes, sensitive fluorescent, anti-counterfeiting technology, 3 D stereo display, bio-medical analysis.
Claims (5)
1. the difluorophenyl Benzazole compounds shown in a formula I:
2. difluorophenyl Benzazole compounds according to claim 1 is as the application of red luminous organic material.
3. the difluorophenyl Benzazole compounds according to right 2 is as the application of the organic up-conversion luminescent material of redness.
4. a preparation method for difluorophenyl Benzazole compounds, is characterized in that, comprises the steps:
Be that pimelinketone and 3-(3-(4-the fluorophenyl)-1-sec.-propyl-1H-indoles-2-base) propenal of 1:2 ~ 2.2 is dissolved in organic solvent by mol ratio, stir lower dropping 10 ~ 20 milliliters of alkaline solutions, at room temperature stirring reaction 10 ~ 15 hours, by in reaction solution impouring 150 ml water, gained solid matter decompress filter, washes with water, drying at room temperature, with ethanol-acetone mixing solutions recrystallization, obtain target compound.
5. the preparation method of difluorophenyl Benzazole compounds according to claim 4, is characterized in that, described organic solvent is methyl alcohol or ethanol; Described alkaline solution is the potassium hydroxide aqueous solution of 15 ~ 20%, or the aqueous sodium hydroxide solution of 15 ~ 20%.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN105801562A (en) * | 2016-04-27 | 2016-07-27 | 中国广州分析测试中心 | Solid-state broadband red light emission organic light-emitting material and preparation method thereof |
| CN107141260A (en) * | 2017-06-06 | 2017-09-08 | 广东省测试分析研究所（中国广州分析测试中心） | A kind of difluorophenyl miazines solid-state green emission luminous organic material and preparation method thereof |
| CN107235964A (en) * | 2017-06-06 | 2017-10-10 | 广东省测试分析研究所（中国广州分析测试中心） | A kind of solid broadband green emission crystalline material and preparation method thereof |
| CN108727365A (en) * | 2018-04-13 | 2018-11-02 | 广东省测试分析研究所（中国广州分析测试中心） | A kind of quinuclidine ketone compounds, its application and preparation method thereof as solid-state green emission luminous organic material |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105801562A (en) * | 2016-04-27 | 2016-07-27 | 中国广州分析测试中心 | Solid-state broadband red light emission organic light-emitting material and preparation method thereof |
| CN105801562B (en) * | 2016-04-27 | 2018-07-27 | 中国广州分析测试中心 | A kind of solid broadband red emission luminous organic material and preparation method thereof |
| CN107141260A (en) * | 2017-06-06 | 2017-09-08 | 广东省测试分析研究所（中国广州分析测试中心） | A kind of difluorophenyl miazines solid-state green emission luminous organic material and preparation method thereof |
| CN107235964A (en) * | 2017-06-06 | 2017-10-10 | 广东省测试分析研究所（中国广州分析测试中心） | A kind of solid broadband green emission crystalline material and preparation method thereof |
| CN107141260B (en) * | 2017-06-06 | 2019-06-14 | 广东省测试分析研究所（中国广州分析测试中心） | A kind of difluorophenyl miazines solid-state green emission luminous organic material and preparation method thereof |
| CN108727365A (en) * | 2018-04-13 | 2018-11-02 | 广东省测试分析研究所（中国广州分析测试中心） | A kind of quinuclidine ketone compounds, its application and preparation method thereof as solid-state green emission luminous organic material |
| CN108727365B (en) * | 2018-04-13 | 2020-10-30 | 广东省测试分析研究所（中国广州分析测试中心） | Quinuclidinone compound, application of quinuclidinone compound as solid green light emitting organic luminescent material and preparation method of quinuclidinone compound |
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Address after: 510070 Yuexiu District, Guangzhou martyrs Road, No. 100, building No. 34, building No. Patentee after: GUANGDONG INSTITUTE OF ANALYSIS (CHINA NATIONAL ANALYTICAL CENTER, GUANGZHOU) Address before: 510070 Yuexiu District, Guangzhou martyrs Road, No. 100, building No. 34, building No. Patentee before: CHINA NATIONAL ANALYTICAL CENTER, GUANGZHOU |
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Address after: 510070 Building 34, No. 100 Xianlie Middle Road, Yuexiu District, Guangzhou City, Guangdong Province Patentee after: Institute of testing and analysis, Guangdong Academy of Sciences (Guangzhou analysis and testing center, China) Address before: 510070 Building 34, No. 100 Xianlie Middle Road, Yuexiu District, Guangzhou City, Guangdong Province Patentee before: GUANGDONG INSTITUTE OF ANALYSIS (CHINA NATIONAL ANALYTICAL CENTER, GUANGZHOU) |