CN106478468A - A kind of fluorescent material based on π pi accumulation compound and preparation method thereof - Google Patents
A kind of fluorescent material based on π pi accumulation compound and preparation method thereof Download PDFInfo
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- CN106478468A CN106478468A CN201610861216.6A CN201610861216A CN106478468A CN 106478468 A CN106478468 A CN 106478468A CN 201610861216 A CN201610861216 A CN 201610861216A CN 106478468 A CN106478468 A CN 106478468A
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- fluorescent material
- aniline
- compound
- phen
- synthetic method
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/42—Separation; Purification; Stabilisation; Use of additives
- C07C303/44—Separation; Purification
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/32—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of salts of sulfonic acids
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/45—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton
- C07C309/46—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton having the sulfo groups bound to carbon atoms of non-condensed six-membered aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a kind of fluorescent material based on π pi accumulation compound and preparation method thereof, belongs to fluorescent material technical field.The compound of the present invention, with 1,10 Phens are primary raw material, aniline 2, and 5 disulfonate sodiums are for aiding in a kind of fluorescent chemicals of Material synthesis.By the auxiliary π pi accumulation of hydrogen bond between 1,10 Phens of 2, the 5 disulfonic acid anion of aniline with protonation, the fluorescence emission wavelengths of material are increased, has expanded the luminescent species of fluorescent material.Present invention also offers the synthetic method of the fluorescent material.The method is easy to operate, and reaction condition is simple, does not pollute, and yield is high, and purity is high.
Description
Technical field
The present invention relates to fluorescent material technical field, and in particular to a kind of fluorescent material based on pi-pi accumulation compound and
Its preparation method.
Background technology
For the influence factor of solid fluorescent material, except the impact of substituted radical, the accumulation mode of fluorescence molecule and point
The impact of sub- interphase interaction is also critically important.In solids, fluorescence molecule is fettered by surrounding environment, is rotated and is vibrated and all receives
To certain restriction, and the Interaction enhanced with adjacent phosphor molecule, these factors can all affect the photoluminescent property of solid.
So by the accumulation mode for changing molecule and intermolecular interaction, it is also possible to reach the purpose for adjusting wavelength of fluorescence.Cause
Adjust, for this, the fracture for being not involved with chemical bond, simply change intermolecular interaction, so this control method is more
There is prospect, also more challenge.
Content of the invention
It is an object of the invention to provide one kind is with 1,10- Phen for primary raw material, and aniline -2,5- disulfonate sodium
Salt has been to aid in a kind of fluorescent material based on pi-pi accumulation compound of Material synthesis.
Present invention also offers the synthetic method of above-mentioned fluorescent material.
A kind of organic compound fluorescent material, concrete structure formula such as formula (I), yield are 80%.
The synthetic method of fluorescent material of the present invention, comprises the steps：
(1) by aniline -2,5- disulfonate sodium is soluble in water, then stirs, and is heated to 80 DEG C, obtains uniform benzene
Amine -2,5- disulfonate sodium the aqueous solution；
(2) 1,10- Phen is dissolved in ethanol, then stirs, 70 DEG C are heated to, obtain uniform 1,10- adjacent luxuriant and rich with fragrance
The ethanol solution of sieve quinoline；
(3) by the ethanol solution of 1,10- Phen and aniline -2, the aqueous solution mixing of 5- disulfonate sodium, then
Stirring, is heated to 90-110 DEG C, flows back 1 hour, after reaction terminates, is cooled to room temperature placement, treats that solvent slowly volatilizees, compound
Gradually separate out；Filter, washed twice with ethanol, deionized water washed once, and finally dry.
The fluorescent material of the present invention, 1,10- Phen are primary raw material, aniline -2, and 5- disulfonate sodium is auxiliary
Material synthesis are a kind of to have epipolic metallic organic framework porous material.Aided in by aniline -2,5- disulfonic acid radical ion
Effect, mutually piling up for 1,10- Phen change fluorescence emission wavelengths.
Fluorescent material has been obtained in the present invention, complex structure has been characterized by single crystal diffraction.Then using glimmering
Light spectroscopic methodology is studied to its Photophysics.
Compared with prior art, the present invention has following technique effect：
(1) the most prominent characteristic of the present invention is to improve material using the trans pi-pi accumulation effect of 1,10- Phen
Fluorescence emission wavelengths.
(2) in the preparation process of the present invention, due to being crystallization process, product purity is high, without accessory substance, without separation
Purification
(3) the 1,10- Phen used in preparation process of the present invention is with aniline -2,5- disulfonate sodium all in market
Middle purchase, so preparation process is saved, preparation process is simple, with low cost.
(4) alkyl substituent of fluorescence molecule affects very little to the solution fluorescence of molecule, but it can be effective in solids
The accumulation mode of ground impact molecule, so fluorescence skeleton can be modified using the alkyl chain of different length, changes the accumulation of molecule
Pattern, Molecular regulator interphase interaction, so as to adjust the wavelength of solid fluorescence.Method of the present invention is easy to operate, reaction
Condition is simple, does not pollute, and yield is high, and purity is high.
Description of the drawings
Fig. 1 is the photo of 1 fluorescent material of embodiment.
Fig. 2 is the single crystal diffraction molecular structure of fluorescent material prepared by embodiment 2.
Fig. 3 is the trans pi-pi accumulation figure of fluorescent material prepared by embodiment 3.
Fig. 4 is Solid fluorescene spectrum figure prepared by embodiment 1 under 315nm is excited.
Specific embodiment
The present invention is further illustrated with reference to embodiments, but the present invention is not limited to following embodiments.
Embodiment 1
1,10- Phen is weighed, is dissolved in 10 milliliters of absolute ethyl alcohols, the mol ratio of 1,10- Phen and ethanol
For 5:1, form homogeneous solution.Aniline -2 are weighed, 5- disulfonic acid mono-sodium salt is dissolved in 10 milliliters of water, aniline -2,5- disulfonic acid
Mono-sodium salt is 2 with the mol ratio of water:1, form homogeneous solution.Two solution are mixed, 90 DEG C are stirred and heated to, flow back 1 hour,
Place after cold filtration, temperature drops to room temperature, slow evaporation solvent, have compound to separate out, filter, washed twice with ethanol, go
Ionized water washed once, and dry.
Embodiment 2
1,10- Phen is weighed, is dissolved in 10 milliliters of absolute ethyl alcohols, the mol ratio of 1,10- Phen and ethanol
For 5:1, form homogeneous solution.Aniline -2 are weighed, 5- disulfonic acid mono-sodium salt is dissolved in 10 milliliters of water, aniline -2,5- disulfonic acid
Mono-sodium salt is 2 with the mol ratio of water:1, form homogeneous solution.Two solution are mixed, 100 DEG C are stirred and heated to, backflow 1 is little
When, to place after cold filtration, temperature drops to room temperature, slow evaporation solvent, has compound to separate out, filters, washed twice with ethanol,
Deionized water washed once, and dry.
Embodiment 3
1,10- Phen is weighed, is dissolved in 10 milliliters of absolute ethyl alcohols, the mol ratio of 1,10- Phen and ethanol
For 5:1, form homogeneous solution.Aniline -2 are weighed, 5- disulfonic acid mono-sodium salt is dissolved in 10 milliliters of water, aniline -2,5- disulfonic acid
Mono-sodium salt is 2 with the mol ratio of water:1, form homogeneous solution.Two solution are mixed, 100 DEG C are stirred and heated to, backflow 1 is little
When, to place after cold filtration, temperature drops to room temperature, slow evaporation solvent, has compound to separate out, filters, washed twice with ethanol,
Deionized water washed once, and dry.
1 result material morphology such as Fig. 1 of embodiment, electromicroscopic photograph.
Molecular structure such as Fig. 2 of 2 material compound of embodiment, single crystal diffraction molecular structure.
Pi-pi accumulation such as Fig. 3 of 3 material compound of embodiment, test result indicate that, between 1,10- Phen molecule
Spacing is 0.357nm.
It is in trans pi-pi accumulation between 1,10- Phen molecule.
3 material fluorescence spectrum of embodiment is tested, and 3 products obtained therefrom powder of embodiment determines fluorescence spectrum, test result indicate that,
Under the exciting of 315nm, the maximum emission peak position of material in 601nm, as shown in Figure 4.
Claims (7)
1. a kind of fluorescent material based on pi-pi accumulation compound, it is characterised in that the structural formula with such as formula (I)：
Yield is up to 89%.
2. the synthetic method of compound fluorescent material described in claim 1, it is characterised in that comprise the steps：
(1) by aniline -2,5- disulfonate sodium is soluble in water, then stirs, and is heated to 80 DEG C, obtains uniform aniline -2,
The 5- disulfonate sodium aqueous solution；
(2) 1,10- Phen is dissolved in ethanol, then stirs, 70 DEG C are heated to, obtain uniform 1,10- Phen
Ethanol solution；
(3) by the ethanol solution of 1,10- Phen and aniline -2, the aqueous solution mixing of 5- disulfonate sodium, then stir,
90-110 DEG C is heated to, is flowed back 1 hour, after reaction terminates, room temperature placement is cooled to, treats that solvent slowly volatilizees, compound is gradually
Separate out.Filter, washed twice with ethanol, deionized water washed once, and finally dry.
3. the synthetic method of compound fluorescent material described in claim 2, it is characterised in that in step (1), aniline -2,
5- disulfonate sodium is 2 with the mol ratio of water:1.
4. the synthetic method of compound fluorescent material described in claim 2, it is characterised in that in step (2), 1,10- is adjacent
Phenanthroline is 5 with the mol ratio of ethanol:1.
5. the synthetic method of compound fluorescent material described in claim 2, it is characterised in that in step (3), aniline -2,
5- disulfonate sodium is 1 with the mol ratio of 1,10- Phen:1.
6. the synthetic method of compound fluorescent material described in claim 2, it is characterised in that in step (3), aniline -2,
5- disulfonate sodium is 1 with the mol ratio of 1,10- Phen:1.
7. the synthetic method of compound fluorescent material described in claim 2, it is characterised in that in step (3), make during backflow
It is spherical condensating tube.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201610861216.6A CN106478468A (en) | 2016-09-29 | 2016-09-29 | A kind of fluorescent material based on π pi accumulation compound and preparation method thereof |
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| CN201610861216.6A CN106478468A (en) | 2016-09-29 | 2016-09-29 | A kind of fluorescent material based on π pi accumulation compound and preparation method thereof |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112898197A (en) * | 2021-02-04 | 2021-06-04 | 南开大学 | Tetrastyrene organic molecular ionic compound, preparation method and application |
| CN114230580A (en) * | 2021-12-24 | 2022-03-25 | 吉林大学 | Multidentate organic ligand, preparation method and application thereof, metal supramolecular polymer and preparation method thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105032484A (en) * | 2015-06-24 | 2015-11-11 | 南京大学 | Solid acid catalysts with dual-center ionic liquid structures and preparation method and application thereof |
-
2016
- 2016-09-29 CN CN201610861216.6A patent/CN106478468A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105032484A (en) * | 2015-06-24 | 2015-11-11 | 南京大学 | Solid acid catalysts with dual-center ionic liquid structures and preparation method and application thereof |
Non-Patent Citations (1)
| Title |
|---|
| 关磊等: ""两个含双磺酸基团化合物的合成晶体结构及荧光性质"", 《无机化学学报》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112898197A (en) * | 2021-02-04 | 2021-06-04 | 南开大学 | Tetrastyrene organic molecular ionic compound, preparation method and application |
| CN112898197B (en) * | 2021-02-04 | 2022-10-28 | 南开大学 | Tetrastyrene organic molecular ionic compound, preparation method and application |
| CN114230580A (en) * | 2021-12-24 | 2022-03-25 | 吉林大学 | Multidentate organic ligand, preparation method and application thereof, metal supramolecular polymer and preparation method thereof |
| CN114230580B (en) * | 2021-12-24 | 2023-01-24 | 吉林大学 | Multidentate organic ligand, preparation method and application thereof, metal supramolecular polymer and preparation method thereof |
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Application publication date: 20170308 |