CN109294560B - Supramolecular azobenzene-2, 2' -aluminum diformate metal gel luminescent material and preparation method thereof - Google Patents
Supramolecular azobenzene-2, 2' -aluminum diformate metal gel luminescent material and preparation method thereof Download PDFInfo
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Abstract
The invention relates to the technical field of supramolecular metal gel luminescent materials, in particular to a supramolecular azobenzene-2, 2' -aluminum diformate metal gel luminescent material and a preparation method thereof. The invention takes azobenzene-2, 2' -dicarboxylic acid as ligand and Al3+As acceptor, DMF-H2O is mixed solvent, and the supermolecular azobenzene-2, 2' -aluminum diformate metal gel luminescent material is prepared by the steps of dissolving, heating, regulating the pH value of the solution and the like. The raw materials used in the invention are simple and easy to obtain, the preparation process is simple and easy to implement, the industrial production is convenient, the product overcomes the defects that the molecular existence form of the complex luminescent material represented by 8-hydroxyquinoline complexes is small, the polymerization degree is low, high molecular materials cannot be formed, and the like, the complex luminescent material is a good high polymeric material and has good photoluminescence performance, and the fluorescence test result shows that the complex luminescent material can emit extremely strong orange light at 603nm and is an ideal soft substance luminescent material.
Description
Technical Field
The invention relates to the technical field of supramolecular metal gel luminescent materials, in particular to a supramolecular azobenzene-2, 2' -aluminum diformate metal gel luminescent material and a preparation method thereof.
Background
The photoluminescence functional material has wide application prospect and research value in the fields of photoelectric devices, information storage, fluorescent switches, fluorescent probes and the like. The electron migration type photoluminescence system has the characteristics of high response sensitivity, good thermal stability, convenient synthesis process and the like. The photosensitive property of the material can be regulated and controlled by designing a main body framework structure, an electron donor molecule, an acceptor molecule and a luminescence center of the material. The use of the strategy can effectively expand the functional characteristics and application prospect of the photoluminescence material.
In recent years, photoelectric materials constructed from aluminum ion-based coordination compounds (e.g., aluminum 8-hydroxyquinoline complexes) have been studied and applied to luminescent materials, luminescent devices, and the like, because of their characteristics such as good film-forming quality, high thermal stability, high carrier mobility, and wide optical band range. The complex luminescent material represented by the 8-hydroxyquinoline complex has no group capable of being further polymerized in the structure, most of the complex luminescent material exists in the form of small molecules which cannot be polymerized, and cannot be used for preparing high-molecular polymeric materials, so that the application and development of the materials are limited. The supermolecule coordination polymer metal gel draws wide attention of domestic and foreign material workers by virtue of unique gelation mode, good stimulus response mechanism, new performances of light, electricity, magnetism, catalysis, oxidation reduction and the like, high polymerization degree and the like. The novel luminescent material with simple and easily obtained sources of design and development raw materials, simple and easy preparation process, low energy consumption, little pollution and good luminescent performance becomes a common target pursued by material scientists.
Disclosure of Invention
In order to overcome the defects and shortcomings of the prior art, the invention mainly aims to provide a preparation method of a supramolecular azobenzene-2, 2' -aluminum diformate metal gel luminescent material.
The invention also aims to provide the supramolecular azobenzene-2, 2' -aluminum diformate metal gel luminescent material prepared by the preparation method.
The invention also aims to provide application of the supramolecular azobenzene-2, 2' -aluminum diformate metal gel luminescent material.
The purpose of the invention is realized by the following technical scheme:
a preparation method of the supramolecular azobenzene-2, 2' -aluminum diformate metal gel luminescent material comprises the following steps:
(1) dissolving azobenzene-2, 2' -dicarboxylic acid in DMF/H2In the O mixed solvent, obtaining azobenzene-2, 2' -bis with the mass volume percentage of 1.54-2.70%Formic acid solution;
(2) adding aluminum salt into the azobenzene-2, 2' -dicarboxylic acid solution prepared in the step (1) under the stirring condition, and uniformly mixing to obtain a clear solution;
(3) dissolving the base in DMF/H2Obtaining alkali liquor in the O mixed solvent;
(4) dropwise adding the alkali liquor prepared in the step (3) into the clear solution prepared in the step (2) at a speed of 20-30D/min under the condition of heating and stirring, so that the pH value of the system is 5-7; then, continuously heating and stirring for 3-5 min to enable the mixture to fully react, and gradually forming a reaction system into a viscous state;
(5) cooling the reaction system after the reaction in the step (4) is completed to below 30 ℃, and then standing for 20-30 min to obtain the supramolecular azobenzene-2, 2' -aluminum diformate metal gel luminescent material;
DMF/H as described in step (1)2In a mixed solvent of O, DMF and H2The volume ratio of O is preferably 1 (0.5-1);
the aluminum salt in the step (2) is preferably at least one of soluble aluminum salts such as aluminum acetate, aluminum chloride and aluminum nitrate;
the mol ratio of the aluminum salt to the azobenzene-2, 2' -dicarboxylic acid in the clear solution in the step (2) is preferably (0.8-1.7): 1;
the alkali in the step (3) is preferably at least one of alkaline substances such as sodium hydroxide, potassium hydroxide, ammonia water and the like;
the concentration of the alkali liquor in the step (3) is preferably 3-5 mol.L-1；
DMF/H as described in step (3)2In a mixed solvent of O, DMF and H2The volume ratio of O is preferably 1 (0.5-1);
the heating and stirring temperature in the step (4) is preferably 30-50 ℃;
the temperature for continuously heating and stirring in the step (4) is preferably 30-50 ℃;
the supermolecular azobenzene-2, 2' -aluminum diformate metal gel luminescent material is prepared by the preparation method;
the supramolecular azobenzene-2, 2' -aluminum diformate metal gel luminescent material is applied to the fields of photoelectric devices, information storage, fluorescent switches, fluorescent probes and the like;
the luminescent material prepared by the invention has the following advantages and effects:
(1) the invention takes azobenzene-2, 2' -dicarboxylic acid as a ligand and Al3+As acceptor, DMF-H2O is mixed solvent, and the supermolecule azobenzene-2, 2' -aluminum diformate metal gel luminescent material is prepared by the processes of dissolving, heating, regulating the pH value of the solution and the like.
(2) The supramolecular azobenzene-2, 2' -aluminum diformate metal gel luminescent material provided by the invention overcomes the defects that a complex luminescent material represented by an 8-hydroxyquinoline complex has a small molecular existence form and a low polymerization degree, cannot form a high polymer material and the like, and is a good high-polymerization-state material.
(3) The supramolecular azobenzene-2, 2 '-aluminum diformate metal gel luminescent material provided by the invention has good photoluminescence performance, and fluorescence test results show that the supramolecular azobenzene-2, 2' -aluminum diformate metal gel luminescent material can emit extremely strong orange light at 603nm (shown in figure 1), and is an ideal soft substance luminescent material.
Drawings
FIG. 1 is a fluorescence spectrum of a supramolecular azobenzene-2, 2' -aluminum diformate metal gel luminescent material.
FIG. 2 is a fluorescence spectrum of azobenzene-2, 2' -dicarboxylic acid.
FIG. 3 is an SEM image of the supramolecular azobenzene-2, 2' -aluminum diformate metal gel luminescent material xerogel.
Detailed Description
The present invention will be described in further detail with reference to examples and drawings, but the present invention is not limited thereto.
In the examples, azobenzene-2, 2' -dicarboxylic acid was purchased from Jinan Hengshi Co.Ltd;
example 1
(1) Dissolving azobenzene-2, 2' -dicarboxylic acid into DMF/H under stirring2O mixed solvent (DMF and H)2The volume ratio of O is 1:0.5), and azobenzene-2, 2' -dicarboxylic acid solution with the mass volume percentage of 1.54 percent is obtained;
(2) under the condition of stirring, adding AlCl3Adding the solution into the azobenzene-2, 2' -dimethyl acid solution prepared in the step (1), and uniformly mixing to obtain a clear solution, wherein AlCl is added into the clear solution3The molar ratio of the azobenzene-2, 2 '-dicarboxylic acid to the azobenzene-2, 2' -dicarboxylic acid is 0.8: 1;
(3) dissolving sodium hydroxide in DMF/H2O mixed solvent (DMF and H)2The volume ratio of O is 1:0.5), the concentration is 3 mol.L-1Sodium hydroxide solution of (a);
(4) dropwise adding the sodium hydroxide solution prepared in the step (3) into the clear solution prepared in the step (2) at the speed of 20D/min under the condition of stirring at the temperature of 30 ℃ to enable the pH value of the system to be 5, and then continuously stirring and reacting for 3min at the temperature of 30 ℃ to enable the reaction system to gradually form a sticky state;
(5) and (4) cooling the reaction system after the reaction in the step (4) is completed to be below 30 ℃, and then standing for 20min to obtain the supramolecular azobenzene-2, 2' -aluminum diformate metal gel luminescent material.
Example 2
(1) Dissolving azobenzene-2, 2' -dicarboxylic acid into DMF/H under stirring2O mixed solvent (DMF and H)2The volume ratio of O is 1:0.75), and 2.21 percent of azobenzene-2, 2' -dicarboxylic acid solution is obtained;
(2) under the condition of stirring, adding AlCl3Adding the solution into the azobenzene-2, 2' -dimethyl acid solution prepared in the step (1), and uniformly mixing to obtain a clear solution, wherein AlCl is added into the clear solution3The molar ratio to azobenzene-2, 2' -dicarboxylic acid is 1.25: 1;
(3) dissolving potassium hydroxide in DMF/H2O mixed solvent (DMF and H)2Volume ratio of O1: 0.75) to give a concentration of 4 mol. L-1Potassium hydroxide solution of (a);
(4) dropwise adding the potassium hydroxide solution prepared in the step (3) into the clear solution prepared in the step (2) at the speed of 25D/min under the stirring condition at 40 ℃ to enable the pH value of the system to be 6, and then continuously stirring and reacting for 4min at 40 ℃ to enable the system to fully react, wherein the reaction system gradually forms a sticky state;
(5) and (4) cooling the reaction system after the reaction in the step (4) is completed to be below 30 ℃, and then standing for 25min to obtain the supramolecular azobenzene-2, 2' -aluminum diformate metal gel luminescent material.
Example 3
(1) Dissolving azobenzene-2, 2' -dicarboxylic acid into DMF/H under stirring2O mixed solvent (DMF and H)2The volume ratio of O is 1:1), and 2.40 percent of azobenzene-2, 2' -dicarboxylic acid solution is obtained;
(2) stirring Al (Ac)3Adding the mixture into the azobenzene-2, 2' -dimethyl acid solution prepared in the step (1), and uniformly mixing to obtain a clear solution, wherein in the clear solution, Al (Ac)3The molar ratio to azobenzene-2, 2' -dicarboxylic acid is 1.50: 1;
(3) dissolving sodium hydroxide in DMF/H2O mixed solvent (DMF and H)2The volume ratio of O is 1:1), the concentration is 5 mol.L-1Sodium hydroxide solution of (a);
(4) dropwise adding the sodium hydroxide solution prepared in the step (3) into the clear solution prepared in the step (2) at the speed of 30D/min under the stirring condition at the temperature of 50 ℃ to enable the pH value of the system to be 7, and then continuously stirring and reacting for 5min at the temperature of 50 ℃ to enable the full reaction system to gradually form a sticky state;
(5) and (4) cooling the reaction system after the reaction in the step (4) is completed to be below 30 ℃, and then standing for 30min to obtain the supramolecular azobenzene-2, 2' -aluminum diformate metal gel luminescent material.
Example 4
(1) Dissolving azobenzene-2, 2' -dicarboxylic acid into DMF/H under stirring2O mixed solvent (DMF and H)2The volume ratio of O is 1:1), and 2.70 percent of azobenzene-2, 2' -dicarboxylic acid solution is obtained;
(2) under stirring, Al (NO) is added3)3Adding the obtained product into the azobenzene-2, 2' -dimethyl acid solution prepared in the step (1), and uniformly mixing to obtain a clear solution, wherein Al (NO) is contained in the clear solution3)3The molar ratio of the azobenzene-2, 2 '-dicarboxylic acid to the azobenzene-2, 2' -dicarboxylic acid is 1.70: 1;
(3) adding strong ammonia water and DMF/H2O mixed solvent (DMF and H)2The volume ratio of O is 1:1) is mixed evenly to obtain the concentration of 5 mol.L-1The aqueous ammonia solution of (1);
(4) dropwise adding the ammonia water solution prepared in the step (3) into the clear solution prepared in the step (2) at the speed of 30D/min under stirring at the temperature of 50 ℃ to enable the pH value of the system to be 6, and then continuously stirring for 5min at the temperature of 50 ℃ to enable the solution to fully react;
(5) and (4) cooling the reaction system after the reaction in the step (4) is completed to be below 30 ℃, and then standing for 30min to obtain the supramolecular azobenzene-2, 2' -aluminum diformate metal gel luminescent material.
Comparative examples
Referring to the reagent amounts and experimental procedures of examples 1 to 4, a single solvent such as DMF, distilled water, ethanol, methanol, acetonitrile, DMSO, methyl chloride, dichloromethane, chloroform and benzene, or a mixed solvent of ethanol, methanol, acetonitrile, DMSO, methyl chloride, dichloromethane, chloroform and benzene in a ratio of water was used instead of DMF/H in examples 1 to 42And the ideal supermolecular azobenzene-2, 2' -aluminum diformate metal gel luminescent material cannot be obtained by using the O mixed solvent.
Effects of the embodiment
The luminescent properties and structural characteristics of the supramolecular azobenzene-2, 2' -aluminum diformate metal gel luminescent materials prepared in examples 1 to 4 were respectively detected.
The luminescence property test shows that: the supramolecular azobenzene-2, 2 '-aluminum diformate metal gel luminescent material prepared in examples 1 to 4 can emit extremely strong orange light at 603nm, and has red shift of more than 223nm compared with the azobenzene-2, 2' -dicarboxylic acid luminescent property of 380nm (figure 2). Wherein, FIG. 1 is a fluorescence spectrum of the supramolecular azobenzene-2, 2 '-aluminum diformate metal gel luminescent material prepared in example 1, and FIG. 2 is a fluorescence spectrum of azobenzene-2, 2' -dicarboxylic acid.
The structural characteristic test shows that: the gel dry products of the supramolecular azobenzene-2, 2' -aluminum diformate metal gel luminescent material prepared in the embodiments 1 to 4 are formed by micro-nano particles with different sizes, and therefore, the gel system is supposed to be a supramolecular polymerization system constructed by binding solvent molecules under the combined action of coordination bonds, hydrogen bonds, pi-pi stacking and van der waals force. Wherein, FIG. 3 is SEM image of xerogel of the supramolecular azobenzene-2, 2' -aluminum diformate metal gel luminescent material prepared in example 1.
The reversibility of acid-base regulation indicates that: the gel can generate gel-sol reversible conversion under the regulation and control of acid and alkali, and the luminescent properties of the sol-gel are different, so that the gel can be used for manufacturing a controllable molecular fluorescent switch.
The above embodiments are illustrative of the preferred embodiments of the present invention and comparative examples, but the embodiments of the present invention are not limited to the above embodiments, and any other changes, modifications, substitutions, combinations, and simplifications which do not depart from the spirit and principle of the present invention should be construed as equivalents and are included in the scope of the present invention.
Claims (10)
1. A preparation method of a supramolecular azobenzene-2, 2' -aluminum diformate metal gel luminescent material is characterized by comprising the following steps:
(1) dissolving azobenzene-2, 2' -dicarboxylic acid in DMF/H2In the O mixed solvent, obtaining an azobenzene-2, 2' -dicarboxylic acid solution with the mass volume percentage of 1.54-2.70%;
(2) adding aluminum salt into the azobenzene-2, 2' -dicarboxylic acid solution prepared in the step (1) under the stirring condition, and uniformly mixing to obtain a clear solution;
(3) dissolving the base in DMF/H2Obtaining alkali liquor in the O mixed solvent;
(4) dropwise adding the alkali liquor prepared in the step (3) into the clear solution prepared in the step (2) at a speed of 20-30D/min under the condition of heating and stirring, so that the pH value of the system is 5-7; then continuously heating and stirring for 3-5 min;
(5) and (3) cooling the reaction system after the reaction in the step (4) is completed to be below 30 ℃, and then standing for 20-30 min to obtain the supramolecular azobenzene-2, 2' -aluminum diformate metal gel luminescent material.
2. The method for preparing supramolecular azobenzene-2, 2' -aluminum diformate metal gel luminescent material according to claim 1, characterized in that:
DMF/H as described in step (1)2In a mixed solvent of O, DMF and H2The volume ratio of O is 1 (0.5-1).
3. The method for preparing supramolecular azobenzene-2, 2' -aluminum diformate metal gel luminescent material according to claim 1, characterized in that:
the aluminum salt in the step (2) is at least one of aluminum acetate, aluminum chloride and aluminum nitrate.
4. The method for preparing supramolecular azobenzene-2, 2' -aluminum diformate metal gel luminescent material according to claim 1, characterized in that:
the molar ratio of the aluminum salt to the azobenzene-2, 2' -dicarboxylic acid in the clear solution in the step (2) is (0.8-1.7): 1.
5. The method for preparing supramolecular azobenzene-2, 2' -aluminum diformate metal gel luminescent material according to claim 1, characterized in that:
the alkali in the step (3) is at least one of sodium hydroxide, potassium hydroxide and ammonia water.
6. The method for preparing supramolecular azobenzene-2, 2' -aluminum diformate metal gel luminescent material according to claim 1, characterized in that:
the concentration of the alkali liquor in the step (3) is 3-5 mol.L-1。
7. The method for preparing supramolecular azobenzene-2, 2' -aluminum diformate metal gel luminescent material according to claim 1, characterized in that:
DMF/H as described in step (3)2In a mixed solvent of O, DMF and H2The volume ratio of O is 1 (0.5-1).
8. The method for preparing supramolecular azobenzene-2, 2' -aluminum diformate metal gel luminescent material according to claim 1, characterized in that:
the heating and stirring temperature in the step (4) is 30-50 ℃.
9. A supramolecular azobenzene-2, 2' -aluminum diformate metal gel luminescent material is characterized by being prepared by the preparation method of any one of claims 1 to 8.
10. The supramolecular azobenzene-2, 2' -aluminum diformate metal gel luminescent material as claimed in claim 9, for applications in the fields of optoelectronic devices, information storage, fluorescence switches and fluorescent probes.
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Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104693220A (en) * | 2015-03-27 | 2015-06-10 | 吉林化工学院 | Preparing method for azobenzene-4, 4'-dicarboxylic acid copper complex with blue light performance |
| CN104710443A (en) * | 2015-03-30 | 2015-06-17 | 吉林化工学院 | Method for preparing azobenzene-4,4'-dicarboxylate copper complex with blue light performance |
| CN104744515A (en) * | 2015-03-31 | 2015-07-01 | 吉林化工学院 | Preparation method of manganese azobenzene-4,4'-dicarboxylate complex with blue-light performance |
| CN104789211A (en) * | 2015-03-30 | 2015-07-22 | 吉林化工学院 | Preparation method for azobenzene-4,4'-dicarboxylic acid cadmium complex with blue light performance |
| CN105669727A (en) * | 2016-01-15 | 2016-06-15 | 天津师范大学 | Preparation method of azobenzene-2,2'-dichloro-4,4'-dicarboxylic acid based cadmium (II) complex and application thereof |
| CN106111198A (en) * | 2016-06-17 | 2016-11-16 | 三峡大学 | A kind of preparation method and applications of the catalyst of metal organic gel materials loaded Ag based on MIL 100 (Al) |
| CN107367426A (en) * | 2017-07-06 | 2017-11-21 | 天津大学 | Regulate and control the method for supermolecular film light softening degree by azobenzene guest molecules |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2938539B1 (en) * | 2008-11-18 | 2012-12-21 | Centre Nat Rech Scient | PROCESS FOR THE PREPARATION OF AROMATIC AROMATIC AZOCARBOXYLATES OF POROUS AND CRYSTALLIZED ALUMINUM OF THE "METAL-ORGANIC FRAMEWORK" TYPE |
-
2018
- 2018-11-06 CN CN201811313768.9A patent/CN109294560B/en active Active
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104693220A (en) * | 2015-03-27 | 2015-06-10 | 吉林化工学院 | Preparing method for azobenzene-4, 4'-dicarboxylic acid copper complex with blue light performance |
| CN104710443A (en) * | 2015-03-30 | 2015-06-17 | 吉林化工学院 | Method for preparing azobenzene-4,4'-dicarboxylate copper complex with blue light performance |
| CN104789211A (en) * | 2015-03-30 | 2015-07-22 | 吉林化工学院 | Preparation method for azobenzene-4,4'-dicarboxylic acid cadmium complex with blue light performance |
| CN104744515A (en) * | 2015-03-31 | 2015-07-01 | 吉林化工学院 | Preparation method of manganese azobenzene-4,4'-dicarboxylate complex with blue-light performance |
| CN105669727A (en) * | 2016-01-15 | 2016-06-15 | 天津师范大学 | Preparation method of azobenzene-2,2'-dichloro-4,4'-dicarboxylic acid based cadmium (II) complex and application thereof |
| CN106111198A (en) * | 2016-06-17 | 2016-11-16 | 三峡大学 | A kind of preparation method and applications of the catalyst of metal organic gel materials loaded Ag based on MIL 100 (Al) |
| CN107367426A (en) * | 2017-07-06 | 2017-11-21 | 天津大学 | Regulate and control the method for supermolecular film light softening degree by azobenzene guest molecules |
Non-Patent Citations (3)
| Title |
|---|
| A layered coordination polymer based on an azodibenzoate linker connected to aluminium (MIL-129);Christophe Volkringer 等;《CrystEngComm》;20100622;第12卷;3225-3228 * |
| Structural Effects in Visible-Light-Responsive Metal–Organic Frameworks Incorporating ortho-Fluoroazobenzenes;Sonia Castellanos 等;《Chem. Eur. J.》;20151130;第22卷;746-752 * |
| 基于偶氮苯的超分子凝胶材料的研究进展;杨润苗 等;《化工进展》;20151231;第34卷;1661-1671 * |
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