CN101307026A - Blue luminescence organic compound and method for synthesizing same - Google Patents
Blue luminescence organic compound and method for synthesizing same Download PDFInfo
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- CN101307026A CN101307026A CNA2007100089744A CN200710008974A CN101307026A CN 101307026 A CN101307026 A CN 101307026A CN A2007100089744 A CNA2007100089744 A CN A2007100089744A CN 200710008974 A CN200710008974 A CN 200710008974A CN 101307026 A CN101307026 A CN 101307026A
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Abstract
The invention provides a blue fluorescent luminescent organic compound and a method for synthesizing the same. The invention relates to synthesis, crystal growth and an application of a yellow fluorescent luminescent organic compound. The molecular formula of the compound is C16H11N3O4, and the space group of the compound is C2/c. The unit cell parameters of the compound are as follows: a is equal to 7.2735(9); b is equal to 17.2359(18); c is equal to 23.744(3); alpha is equal to 90 degrees; beta is equal to 93.235(2) degrees; gamma is equal to 90 degrees; Z is equal to 8, and the unit cell volume V of the compound is equal to 2972.0(6)<3>. The compound is prepared by adopting three-step reaction, namely diazo reaction, azide substitution and cyclic addition. The compound emits strong blue fluorescence nearby 430 nm. 1-(3, 5-phthalic acid)-4-phenyl-1, 2, 3-triazole can become a novel fluorescent luminescent material and can be used for manufacturing fluorescent luminescent devices.
Description
Technical field
The present invention relates to a kind of synthetic, crystal growth and application of yellow fluorescence luminous organic compound.
Background technology
Material molecule, atomic absorption optical radiation are excited, and launch the light identical or longer with absorbing wavelength again, are called photoluminescence, and modal is fluorescence and phosphorescence, and comparatively speaking, the research of fluorescent emission is more deep, use more extensive.The organic compound that has than the hyperfluorescence luminous power has crucial potential using value, can develop as new function material, as luminescent dye, laser dyes, sensitizing dye, fluorescent probe etc.The fluorescence radiation behavior of organic compound, comprise the emissive porwer (fluorescence quantum yield) of fluorescence radiation and the position of emission peak wavelength etc., not only relevant with the molecular structure of compound, substituent characteristic etc., but also and polarity, the viscosity of molecule environment of living in, the situation of being obstructed, molecule conformation and the aggregation structure etc. in these environment substantial connection is arranged.To the molecular designing of organic compound and synthetic and, be a problem in science that receives much concern to the research of its structure and property relationship with fluorescent emission ability always.Therefore the research with fluorescent emission ability organic compound structure and property relationship had important scientific meaning and wide application prospect.
A kind of compound with strong luminous power, its molecular structure should have intramolecularly conjugated two dimensional structure usually and introducing pushes away-drawing electron group at the molecule two ends, to strengthen intramolecular charge transport capability.1-(3, the 5-phthalic acid)-4-phenyl-1,2, the 3-triazole might be as fluorescence luminescent material because of himself characteristic: (1) exists phenyl ring and 1,2, the electron conjugated system of 3-triazole five-ring and strong π-π * absorption jump have possessed the ability of emission than hyperfluorescence, in field of light emitting materials application promise in clinical practice are arranged; (2) there is the carboxyl drawing electron group, helps intramolecular charge transfer; (3) introduce difference on the carboxyl position and push away-drawing electron group, the luminescence law of this compounds is inquired in regulating compound luminous.At present both at home and abroad about 1, therefore 2, the report of the luminosity of 3-3-triazole compounds is few, to the research of synthetic, the structure and the luminosity of this compounds, help designing and synthesizing luminophor, widen the screening scope of luminescent material with high-fluorescence quantum yield.
Summary of the invention
Purpose of the present invention just is synthetic a kind of yellow fluorescence luminous organic compound 1-(3, the 5-phthalic acid)-4-phenyl-1,2, the 3-triazole, and molecular formula is C
16H
11N
3O
4, its synthetic technology route is as follows:
The present invention includes following technical scheme:
1. blue streak fluorescence radiation organic compound, this compound molecule formula is C
16H
11N
3O
4, spacer is C2/c, cell parameter is a=7.2735 (9)
B=17.2359 (18)
C=23.744 (3)
α=90 °, β=93.235 (2) °, γ=90 °, Z=8, unit-cell volume V=2972.0 (6)
3
2. the preparation method of the blue streak fluorescence radiation organic compound of an item 1 adopts doazo reaction, nitrine replacement and cyclic addition three-step reaction to be prepared.
3. as the preparation method of 2 described blue streak fluorescence radiation organic compound, raw material 5-amido m-phthalic acid, NaNO
2And NaN
3Mol ratio be (1～2): (1～2): (1～2), adopt concentrated hydrochloric acid and H
2O is a mixed solvent, 0～5 ℃ of temperature of reaction.
4. as the preparation method of 2 a described blue streak fluorescence radiation organic compound, the mol ratio of raw material 5-phenylazide dioctyl phthalate and phenylacetylene is (1～2): (1～2), adopt DMSO and H
2O is a mixed solvent, 50～70 ℃ of temperature of reaction.
5. the purposes of the blue streak fluorescence radiation organic compound of an item 1, this compound is as fluorescence luminescent material and device.
1-(3, the 5-phthalic acid)-4-phenyl-1,2, the 3-triazole may become a kind of new fluorescence luminescent material, and can be used for making the fluorescence radiation device.
Embodiment
We select 5-amido m-phthalic acid and NaNO
2As raw material,, adopt concentrated hydrochloric acid and H
2O is a mixed solvent, adds NaN under the ice bath reaction conditions
3, replace preparation intermediate product 5-phenylazide dioctyl phthalate through doazo reaction and nitrine; Adopt DMSO and H again
2O is a mixed solvent, at Cu
+(by vitamin C sodium salt reduction CuSO
4Obtaining) under the katalysis, intermediate product 5-phenylazide dioctyl phthalate and phenylacetylene issue the generation cycloaddition reaction at heating condition, by cooling, the 1-that grown (3, the 5-phthalic acid)-4-phenyl-1,2, the monocrystalline of 3-triazole.Its molecular structure shows as basic copline.The fluorescence spectrum test shows, 1-(3, the 5-phthalic acid)-4-phenyl-1,2, the 3-triazole sends stronger blue-fluorescence near 430nm.
1-provided by the invention (3, the 5-phthalic acid)-4-phenyl-1,2,3-triazole adopt doazo reaction, nitrine replacement and cyclic addition three-step reaction to prepare the product pyrosol, grow crystal by cooling again.Solvent is DMSO and H
2The mixed solvent of O.
In doazo reaction and the nitrine substitution reaction process, reaction mixture is cooled to 0 ℃, stirring reaction 30 minutes.In the cyclic addition reaction process, reaction mixture is heated to 65 ℃, stirring reaction 24 hours cools, and grows crystal.
Embodiment 1
Take by weighing 5-amido m-phthalic acid (25mmol), add dense HCl and H
2Each 8mL of O, be heated to the dissolving of all solid after, pour the H that is cooled to 0 ℃ into
2Stand-by among the O (400mL); Take by weighing NaNO
2(25mmol), add H
2O (5mL), be cooled to 0 ℃ after, slowly splash in the above-mentioned 5-amido m-phthalic acid solution and fast after 30 fens kinds of stir about, add NaN
3The aqueous solution (30mmol NaN
3Be dissolved in 10mLH
2Make among the O), generate white precipitate, suction filtration cleans after drying with distilled water and gets intermediate product 5-phenylazide dioctyl phthalate.Take by weighing intermediate product 5-phenylazide dioctyl phthalate (10mmol), add stupid acetylene (1.1mL), DMSO (40mL) and H
2O (10mL), stirring reaction added sodium ascorbate (1mmol) and CuSO after 10 minutes
4(0.1mmol), be heated to 65 ℃ and stir after 24 hours, the ice bath naturally cooling grows crystal.Analyze through the X ray single crystal diffraction, determine that this crystal is 1-(3, the 5-phthalic acid)-4-phenyl-1,2,3-triazole (molecular formula: C
16H
11N
3O
4).
The crystal grinding of preparation is evenly obtained pressed powder, carry out the fluorescence radiation performance test on Edinburgh F920 fluorescence spectrophotometer, the result shows, send stronger blue-fluorescence near 430nm.
Claims (5)
1. blue streak fluorescence radiation organic compound, it is characterized in that: this compound molecule formula is C
16H
11N
3O
4, spacer is C2/c, cell parameter is
α=90 °, β=93.235 (2) °, γ=90 °, Z=8, unit-cell volume
2. the preparation method of the blue streak fluorescence radiation organic compound of a claim 1 is characterized in that: adopt doazo reaction, nitrine replacement and cyclic addition three-step reaction to be prepared.
3. the preparation method of blue streak fluorescence radiation organic compound as claimed in claim 2 is characterized in that: raw material 5-amido m-phthalic acid, NaNO
2And NaN
3Mol ratio be (1～2): (1～2): (1～2), adopt concentrated hydrochloric acid and H
2O is a mixed solvent, 0～5 ℃ of temperature of reaction.
4. the preparation method of blue streak fluorescence radiation organic compound as claimed in claim 2 is characterized in that: the mol ratio of raw material 5-phenylazide dioctyl phthalate and phenylacetylene is (1～2): (1～2), adopt DMSO and H
2O is a mixed solvent, 50～70 ℃ of temperature of reaction.
5. the purposes of the blue streak fluorescence radiation organic compound of a claim 1, it is characterized in that: this compound is as fluorescence luminescent material and device.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2007100089744A CN101307026A (en) | 2007-05-17 | 2007-05-17 | Blue luminescence organic compound and method for synthesizing same |
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| CNA2007100089744A CN101307026A (en) | 2007-05-17 | 2007-05-17 | Blue luminescence organic compound and method for synthesizing same |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101993421A (en) * | 2009-08-25 | 2011-03-30 | 中国科学院福建物质结构研究所 | Synthesis and application of blue-fluorescence luminous zinc metal complex |
| CN104119286A (en) * | 2014-07-30 | 2014-10-29 | 齐鲁工业大学 | Condensed triazole benzaldehyde p-phenylenediamine bis-Schiff base and preparation method thereof |
| CN104987631A (en) * | 2015-07-21 | 2015-10-21 | 西安交通大学 | Method for preparing fluorescent polymer with poly(vinylidene fluoride-chlorotrifluoroethylene) |
| CN105753794A (en) * | 2016-03-31 | 2016-07-13 | 华东理工大学 | Design of preparing novel organic OLED reagent from alcohol and application thereof |
| CN105801499A (en) * | 2016-04-15 | 2016-07-27 | 华东理工大学 | Design of preparing novel OLED reagent from ketene and application thereof |
| CN105859644A (en) * | 2016-04-15 | 2016-08-17 | 华东理工大学 | Design and application of olefin to preparation of novel organic OLED reagent |
-
2007
- 2007-05-17 CN CNA2007100089744A patent/CN101307026A/en active Pending
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101993421A (en) * | 2009-08-25 | 2011-03-30 | 中国科学院福建物质结构研究所 | Synthesis and application of blue-fluorescence luminous zinc metal complex |
| CN101993421B (en) * | 2009-08-25 | 2014-04-16 | 中国科学院福建物质结构研究所 | Synthesis and application of blue-fluorescence luminous zinc metal complex |
| CN104119286A (en) * | 2014-07-30 | 2014-10-29 | 齐鲁工业大学 | Condensed triazole benzaldehyde p-phenylenediamine bis-Schiff base and preparation method thereof |
| CN104119286B (en) * | 2014-07-30 | 2017-06-20 | 淄博职业学院 | A kind of triazole benzaldehyde-p-phenylenediamine bi-schiff base and preparation method thereof |
| CN104987631A (en) * | 2015-07-21 | 2015-10-21 | 西安交通大学 | Method for preparing fluorescent polymer with poly(vinylidene fluoride-chlorotrifluoroethylene) |
| CN105753794A (en) * | 2016-03-31 | 2016-07-13 | 华东理工大学 | Design of preparing novel organic OLED reagent from alcohol and application thereof |
| CN105801499A (en) * | 2016-04-15 | 2016-07-27 | 华东理工大学 | Design of preparing novel OLED reagent from ketene and application thereof |
| CN105859644A (en) * | 2016-04-15 | 2016-08-17 | 华东理工大学 | Design and application of olefin to preparation of novel organic OLED reagent |
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Open date: 20081119 |