CN106749353B - A kind of fluorescent type coordination polymer and preparation method thereof - Google Patents
A kind of fluorescent type coordination polymer and preparation method thereof Download PDFInfo
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- CN106749353B CN106749353B CN201611105448.5A CN201611105448A CN106749353B CN 106749353 B CN106749353 B CN 106749353B CN 201611105448 A CN201611105448 A CN 201611105448A CN 106749353 B CN106749353 B CN 106749353B
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Abstract
The present invention provides one kind fluorescent type coordination polymers as shown in formula (I), present invention also provides the preparation methods of the fluorescent type coordination polymer, it include: by cadmium salt, Isosorbide-5-Nitrae-phenylenediacetic Acid, 2,4,6- tri- (pyridyl group) -1,3,5- triazines mix in a solvent with the guest molecule of electron rich type, obtain mixed liquor, the mixed liquor is subjected to solvent thermal reaction, obtains fluorescent type coordination polymer.Fluorescent type coordination polymer provided by the present application is two-dimensional layered structure, guest molecule is in interlayer, there is strong conjugation with layer inner plane type ligand tpt, to show a degree of charge transfer effect, simultaneously because encapsulating different guest molecules, it is different from plane tpt ligand active force, and show different colors；[Cd2(tpt)2(1,4‑pda)2]·PAH (Ⅰ)。
Description
Technical field
The present invention relates to fluorescence coordination polymer technical field more particularly to a kind of fluorescent type coordination polymer and its preparations
Method.
Background technique
The coordination polymer of fluorescent type is provided due to adjustable property and charming structure for the development of solid state fluorescent material
Good platform.In recent years, host-guest chemistry is also that the coordination polymer of fluorescent type opens new stage, due to functionalization
Guest molecule can be controllably encapsulated into coordination polymer by hydrogen bond action, pi-pi accumulation effect, electrostatic interaction etc.,
To keep optical property far different.Correspondingly, they shine mainly from main body frame, guest molecule, both it is simple
Coordinated between superposition or Subjective and Objective.Wherein, the research about effective Subjective and Objective synergistic effect, since it is conducive to pass through
The interaction of Subjective and Objective electric charge transfer leads to adjustable wide in range luminescent properties, and receives more and more attention.However, this kind of
Process in a certain degree for be seldom mined, mainly since it needs relatively harsh condition to need suitable donor
Just be conducive to obtain the interaction of Subjective and Objective electric charge transfer by appropriate arrangement with receptor.Therefore, such adjustable coordination
The acquisition of polymer is still a major challenge.
Currently, guest molecule is introduced into frame by functionalization guest molecule in such a way that infusion method is introduced into, reach hair
The totally different material of optical property.But the fluorescent type coordination polymer of this method preparation has shortcomings, and such as: 1) due to object
Molecule enters frame by the modes such as impregnating, and the active force of guest molecule and frame is not strong, and guest molecule is possible to leak,
The stability of material is worthy of consideration；2) during the Study on Complexes for the host-guest interaction that infusion method obtains, to guest molecule
The content ratio of son in the frame is difficult to control；3) complex for the host-guest interaction that infusion method obtains is due to its active force
Be not it is very strong, shining is generally from main body or the independent of object shines, and controllable its broadband luminescent properties of adjusting are more stranded
It is difficult.
Summary of the invention
Present invention solves the technical problem that being to provide a kind of coordination polymer of fluorescent type, fluorescent type provided by the present application
Coordination polymer stability is preferable, and has regulatable luminescent properties.
In view of this, this application provides one kind fluorescent type coordination polymer as shown in formula (I),
[Cd2(tpt)2(1,4-pda)2] PAH (I),
Wherein, 2 tpt, 4,6- tri- (pyridyl group) -1,3,5-triazines；
1,4-pda is 1,4- phenylenediacetic Acid；
PAH is the guest molecule of electron rich type.
Preferably, the PAH is the guest molecule of the electron rich type containing phenyl ring.
Preferably, the PAH is benzophenanthrene, pyrene, perylene or coronene.
Preferably, the fluorescent type coordination polymer is two-dimensional layered structure, and the guest molecule is located at interlayer, with tpt
Form conjugation.
Preferably, the fluorescent type coordination polymer is rhombic system, and cell parameter is respectivelyAngle is respectively 90 °, 90 °, 90 °.
Present invention also provides the preparation methods of the fluorescent type coordination polymer described in above scheme, comprising:
The guest molecule of cadmium salt, 1,4- phenylenediacetic Acid, (the pyridyl group) -1,3,5- triazine of 2,4,6- tri- and electron rich type is existed
It is mixed in solvent, obtains mixed liquor；The mixed liquor is subjected to solvent thermal reaction, obtains fluorescent type coordination polymer.
Preferably, the guest molecule PAH is benzophenanthrene, pyrene, perylene or coronene, and the cadmium salt is cadmium nitrate or height
Cadmium chlorate.
Preferably, the solvent is ethyl alcohol, water and n,N-Dimethylformamide.
Preferably, the cadmium salt, Isosorbide-5-Nitrae-phenylenediacetic Acid, 2,4,6- tri- (pyridyl group) -1,3,5-triazines and electron rich type
The molar ratio of guest molecule is 2:2:1:1.
Preferably, the temperature of the solvent thermal reaction is 80~95 DEG C, and the time is for 24 hours.
This application provides a kind of fluorescent type coordination polymer with formula (I) structure, the fluorescent type polycomplexations of the application
Closing object and having been constructed using the plane ligand tpt of short of electricity subtype and the guest molecule PAH of electron rich type has Subjective and Objective electric charge transfer
The fluorescent type coordination polymer of interaction, the complex are deposited due to showing as two-dimensional layered structure, guest molecule in structure
It is interlayer, there is stronger conjugation between guest molecule and plane ligand, so that fluorescence coordination polymer is stablized
Property it is preferable, guest molecule be not easy from interlayer remove；There are suitable electron donors for the fluorescent type coordination polymer of the application simultaneously
With receptor, thus show host and guest's figure electric charge transfer induction fluorescence property.
Detailed description of the invention
Fig. 1 is the structural schematic diagram of complex prepared by the embodiment of the present invention 1；
Fig. 2 is the structural schematic diagram of complex prepared by the embodiment of the present invention 3；
Fig. 3 is the UV, visible light performance chart of complex 1~5 of the present invention；
Fig. 4 is the fluorescent emission performance chart of complex 1~5 of the present invention；
Fig. 5 is the hot weight curve of complex 1~5 of the present invention.
Specific embodiment
For a further understanding of the present invention, the preferred embodiment of the invention is described below with reference to embodiment, still
It should be appreciated that these descriptions are only further explanation the features and advantages of the present invention, rather than to the claims in the present invention
Limitation.
The embodiment of the invention discloses one kind fluorescent type coordination polymer as shown in formula (I),
[Cd2(tpt)2(1,4-pda)2] PAH (I),
Wherein, 2 tpt, 4,6- tri- (pyridyl group) -1,3,5-triazines；
1,4-pda is 1,4- phenylenediacetic Acid；
PAH is the guest molecule of electron rich type.
Fluorescent type coordination polymer provided by the present application utilizes tri- (pyridyl group) -1 plane ligand 2,4,6- of short of electricity subtype,
The 3,5- triazine tpt and guest molecule PAH of electron rich type has constructed out the fluorescent type with the interaction of Subjective and Objective electric charge transfer
Coordination polymer.
Fluorescent type coordination polymer of the present invention has two-dimensional double-layer layer structure in structure, and guest molecule PAH is deposited
It is interlayer, there is stronger conjugation between guest molecule PAH and plane ligand tpt, make polymer stabilizing, and guest molecule
Son is not easy to shift from interlayer, so that fluorescent type coordination polymer shows a degree of charge transfer effect.
According to the present invention, the guest molecule of the electron rich type can be embedding for benzophenanthrene (triphenylene), pyrene, dinaphthyl
Benzene or coronene (coronene), when guest molecule changes, red shift occurs for the maximum emission peak of polymer, due to guest molecule
Red shift degree difference that is different from the interaction force of plane ligand tpt in main body frame and leading to polymer, emission peak positions
Difference, luminescent color is also different, and reflection is on chromaticity coordinates, and the corresponding color of the polymer that guest molecule difference obtains is not yet
Together, corresponding respectively to blue (no guest molecule), green (benzophenanthrene), yellow (pyrene), orange (coronene) and red, (dinaphthyl is embedding
Benzene), the introducing for further illustrating guest molecule can be such that the emission band of coordination polymer is effectively regulated and controled.
Herein described fluorescent type coordination polymer belongs to rhombic system, and cell parameter is respectivelyAngle is respectively 90 °；When guest molecule difference,
The fluorescent type coordination polymer cell parameter acquired is still above-mentioned numerical value, and only specific corresponding object is changed.Example
Such as: [Cd2(tpt)2(1,4-pda)2] triphenylene fluorescent type coordination polymer cell parameter are as follows: α=γ=β=90 °；[Cd2(tpt)2(1,
4-pda)2] coronene fluorescent type coordination polymer cell parameter are as follows:α=γ=β=90 °.
Present invention also provides the preparation methods of the fluorescent type coordination polymer, comprising the following steps:
By cadmium salt, 1,4- phenylenediacetic Acid, 2,4,6- tri- (pyridyl group) -1,3,5- triazine and electron rich type guest molecule
PAH is mixed in a solvent, obtains mixed liquor, and the mixed liquor is carried out solvent thermal reaction, obtains fluorescent type coordination polymer.
The present invention utilizes tri- (the pyridyl group) -1,3,5- triazine (tpt) of plane ligand 2,4,6- of electron deficient, electron rich type
The fluorescent type that guest molecule PAH, cadmium salt, 1,4- phenylenediacetic Acid ligand obtain a series of water stability under the conditions of solvent heat is matched
Position polymer.
During preparing fluorescent type coordination polymer, raw material is mixed first, i.e., by cadmium salt, Isosorbide-5-Nitrae-phenylenediacetic Acid,
2,4,6- tri- (pyridyl group) -1,3,5-triazines mix in a solvent with the guest molecule PAH of electron rich type, obtain mixed liquor.?
During Compound mixed solution, the cadmium salt is preferably cadmium nitrate or cadmium perchlorate.The guest molecule PAH of the electron rich type is preferred
For benzophenanthrene (triphenylene), pyrene, coronene (coronene) or perylene.The solvent is that those skilled in the art are ripe
The solvent known is not particularly limited this application, however, to ensure that above-mentioned raw materials can sufficiently dissolve, the solvent is excellent
It is selected as the mixed solution of ethyl alcohol, water and n,N-Dimethylformamide, and volume ratio is 2:2:4.Above-mentioned solvent is the pure examination of analysis
Agent.The cadmium salt, 1,4- phenylenediacetic Acid, (the pyridyl group) -1,3,5- triazine of 2,4,6- tri- are rubbed with the guest molecule of electron rich type
You are than being preferably 2:2:1:1.
After obtaining mixed liquor, the mixed liquor is then carried out solvent thermal reaction by the application, obtains fluorescent type polycomplexation
Close object.The solvent thermal reaction is solvent thermal reaction well known to those skilled in the art, is not particularly limited to this application.
Preferably, the temperature of the solvent thermal reaction is preferably 80~95 DEG C, and the time is for 24 hours.Mixed liquor in the application is logical
Solvent heat is crossed, the crystalline material that shape is similar but color is totally different, i.e. fluorescent type coordination polymer are obtained.Pure state is glimmering in order to obtain
Light type coordination polymer, after solvent thermal reaction, the crystalline material that the application preferably uses dehydrated alcohol to wash is dry
Pure state crystallofluorescence type coordination polymer is obtained afterwards.
The present invention provides one kind fluorescent type coordination polymers as shown in formula (I), and wherein tpt is the plane of short of electricity subtype
Ligand, PAH are the guest molecule of electron rich type, and the application utilizes the plane ligand of short of electricity subtype and the guest molecule of electron rich type
The fluorescent type coordination polymer for providing the interaction of Subjective and Objective electric charge transfer is constructed under the conditions of solvent heat.Fluorescent type coordination
For polymer due to showing as two-dimensional layered structure in structure, guest molecule is present in interlayer, guest molecule and plane ligand it
Between there is stronger conjugation so that the material settling out, and guest molecule is not easy to remove from interlayer；Such is steady simultaneously
Qualitative fluorescent type material, due to showing the glimmering of host and guest's figure electric charge transfer induction there are suitable electron donor and receptor
Optical property has potential application in sensing, fluorescent lamp materials science field.
For a further understanding of the present invention, below with reference to embodiment to the system of fluorescent type coordination polymer provided by the invention
Preparation Method is described in detail, and protection scope of the present invention is not limited by the following examples.
Embodiment 1
It is constructed under the conditions of solvent heat using the plane ligand of short of electricity subtype and the guest molecule of electron rich type and has provided master
The fluorescent type coordination polymer 2 of object electric charge transfer interaction, specifically include the following steps:
1) by 16.6 milligrams of (0.1 mM) 1,4- phenylenediacetic Acids, 12.0 milligrams of tri- (pyridines of (0.1 mM) 2,4,6-
Base) -1,3,5- triazine (tpt), 30.8 milligrams of (0.1 mM) cadmium nitrates and 10 milligrams of benzophenanthrenes are dissolved in 4 milliliters of N, N- bis-
In the bottle of methylformamide (DMF), 2 milliliters of ethyl alcohol and 2 milliliters of water mixed solvents, mixed solution is obtained；
2) above-mentioned mixed solution is reacted for 24 hours in 80~95 DEG C, then is washed 2~3 times using dehydrated alcohol, after dry,
Obtain light green color bulk-shaped monocrystal [Cd2(tpt)2(1,4-pda)2] triphenylene, it is named as complex 2, and pass through monocrystalline
X-ray diffraction experiment analyzes its specific structure, analyzes the results show that complex 2 belongs to rhombic system P212121, cell parameter is α=γ=β=90 °.Fig. 1 is complex 2
Structural schematic diagram, wherein Fig. 1 a is the coordination context diagram of the metal Cd ion of complex 2, metal Cd ion and three Isosorbide-5-Nitraes-
Pyridine nitrogen atom in five carboxyl oxygens and two tpt ligands of pda ligand connects the pentagonal bipyramid type coordination to form seven coordinations；
Fig. 1 b be complex 2 asymmetric cell figure, in its asymmetric cell containing there are two metal ion, two Isosorbide-5-Nitrae-pda ligands,
Two tpt and benzophenanthrene guest molecules；Fig. 1 c is the double-deck 2D structure chart of complex 2, Cd ion by Isosorbide-5-Nitrae-pda and
Tpt is connected to form two-dimensional double-layer structure；Fig. 1 d is the Magnetic Properties of Three-Dimensional Supramolecular Complex figure of complex 2, and benzophenanthrene be in interlayer, show and
The stronger conjugation of tpt ligand, distance between the two are
Embodiment 2
It is constructed under the conditions of solvent heat using the plane ligand of short of electricity subtype and the guest molecule of electron rich type and has provided master
The fluorescent type coordination polymer 2 of object electric charge transfer interaction, specifically include the following steps:
1) by 16.6 milligrams of (0.1 mM) 1,4- phenylenediacetic Acids, 12.0 milligrams of tri- (pyridines of (0.1 mM) 2,4,6-
Base) -1,3,5- triazine (tpt), 40 milligrams of (0.1 mM) cadmium perchlorates and 10 milligrams of benzophenanthrenes are dissolved in 4 milliliters of N, N- bis-
In the bottle of methylformamide (DMF), 2 milliliters of ethyl alcohol and 2 milliliters of water mixed solvents, mixed solution is obtained；
2) above-mentioned mixed solution is reacted for 24 hours in 80~95 DEG C, then adopts dehydrated alcohol and washs 2~3 times, obtained after dry
Light green color bulk-shaped monocrystal complex 2.
Embodiment 3
It constructs and provides under the conditions of solvent heat using the plane ligand of short of electricity subtype and the guest molecule coronene of electron rich type
The fluorescent type coordination polymer 4 for thering is Subjective and Objective electric charge transfer to interact, specifically include the following steps:
1) by 16.6 milligrams of (0.1 mM) 1,4- phenylenediacetic Acids, 12.0 milligrams of tri- (pyridines of (0.1 mM) 2,4,6-
Base) -1,3,5- triazine (tpt), 42 milligrams of (0.1 mM) cadmium perchlorates and 10 milligrams of coronene are dissolved in 4 milliliters of N, N- diformazan
In the bottle of base formamide (DMF), 2 milliliters of ethyl alcohol and 2 milliliters of water mixed solvents, mixed solution is obtained；
2) above-mentioned mixed solution is reacted for 24 hours in 80~95 DEG C, then adopts dehydrated alcohol and washs 2~3 times, obtained after dry
Light green color bulk-shaped monocrystal [Cd2(tpt)2(1,4-pda)2] coronene complex 4, and pass through single crystal X-ray diffraction experiment point
Its specific structure is analysed, is analyzed the results show that complex 4 belongs to rhombic system Pnma, cell parameter is α=γ=β=90 °.Fig. 2 is complex
4 structural schematic diagram, wherein Fig. 2 a is the coordination context diagram of the metal Cd ion of complex 4, metal Cd ion and three Isosorbide-5-Nitraes-
Pyridine nitrogen atom in five carboxyl oxygens and two tpt ligands of pda ligand connects the pentagonal bipyramid type coordination to form seven coordinations；
Fig. 2 b be complex 4 asymmetric cell figure, in its asymmetric cell containing a metal ion, an Isosorbide-5-Nitrae-pda ligand,
One tpt and half of coronene guest molecule；Fig. 2 c is the double-deck 2D structure chart of complex 4, and Cd ion passes through Isosorbide-5-Nitrae-pda and tpt
It is connected to form two-dimensional double-layer structure；Fig. 2 d is the Magnetic Properties of Three-Dimensional Supramolecular Complex figure of complex 4；Benzophenanthrene is in interlayer, shows and matches with tpt
The stronger conjugation of body, distance between the two are
Embodiment 4
Complex 1, complex 3 and complex 5 are prepared according to the method for embodiment 1, and difference is: not wrapping in complex 1
Guest molecule is included, the guest molecule in complex 3 is pyrene, and the guest molecule in complex 5 is perylene.
The fluorescence quantum yield and fluorescence lifetime tables of data of 1 complex 1~5 of table
Fig. 3 is the UV, visible light and fluorescence property curve graph of complex 1~5, and Fig. 4 is the fluorescent emission of complex 1~5
Energy curve graph, Fig. 5 are the hot weight curve of complex 1~5, and table 1 is the fluorescence quantum yield and fluorescence lifetime of complex 1~5
Tables of data.From the figure 3, it may be seen that coordination polymer, after introducing benzophenanthrene, a new absorption peak appears in 350~450nm model
In enclosing, due to the charge transfer effect between benzophenanthrene and tpt；For fluorescence angle, after introducing benzophenanthrene, cooperation
For the main body of no guest molecule, a degree of red shift occurs object 2 for maximum emission peak (495nm).By Fig. 3~5 with
Table 1 is it is found that after guest molecule PAH introducing, and the thermal stability of complex improves, and fluorescent emission is in a wide range；Material
Fluorescence quantum yield also have greatly improved；Illustrate complex 2~5 fluorescent optical sensor, in terms of potential answer
With.
The above description of the embodiment is only used to help understand the method for the present invention and its core ideas.It should be pointed out that pair
For those skilled in the art, without departing from the principle of the present invention, the present invention can also be carried out
Some improvements and modifications, these improvements and modifications also fall within the scope of protection of the claims of the present invention.
The foregoing description of the disclosed embodiments enables those skilled in the art to implement or use the present invention.
Various modifications to these embodiments will be readily apparent to those skilled in the art, as defined herein
General Principle can be realized in other embodiments without departing from the spirit or scope of the present invention.Therefore, of the invention
It is not intended to be limited to the embodiments shown herein, and is to fit to and the principles and novel features disclosed herein phase one
The widest scope of cause.
Claims (6)
1. a kind of fluorescent type coordination polymer as shown in formula (I),
[Cd2(tpt)2(1,4-pda)2] PAH (I),
Wherein, 2 tpt, 4,6- tri- (4- pyridyl group) -1,3,5-triazines；
1,4-pda is 1,4- phenylenediacetic Acid root；
PAH is benzophenanthrene, pyrene, perylene or coronene；
The fluorescent type coordination polymer is two-dimensional layered structure, and the guest molecule is located at interlayer, forms conjugation effect with tpt
It answers；
The fluorescent type coordination polymer is rhombic system, and cell parameter is respectively Angle is respectively 90 °, 90 °, 90 °.
2. the preparation method of fluorescent type coordination polymer described in claim 1, comprising:
By cadmium salt, Isosorbide-5-Nitrae-phenylenediacetic Acid, 2,4,6- tri- (4- pyridyl group) -1,3,5-triazines mix in a solvent with guest molecule,
Obtain mixed liquor；The mixed liquor is subjected to solvent thermal reaction, obtains fluorescent type coordination polymer；The guest molecule is benzo
Phenanthrene, pyrene, perylene or coronene.
3. preparation method according to claim 2, which is characterized in that the cadmium salt is cadmium nitrate or cadmium perchlorate.
4. preparation method according to claim 2, which is characterized in that the solvent is ethyl alcohol, water and N, N- dimethyl methyl
Amide.
5. preparation method according to claim 2, which is characterized in that the cadmium salt, Isosorbide-5-Nitrae-phenylenediacetic Acid, 2,4,6- tri-
(4- pyridyl group) -1,3,5- triazine and the molar ratio of guest molecule are 2:2:1:1.
6. preparation method according to claim 2, which is characterized in that the temperature of the solvent thermal reaction is 80~95 DEG C,
Time is for 24 hours.
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| CN103450234A (en) * | 2013-07-29 | 2013-12-18 | 南开大学 | Cadmium coordination polymer and preparation method thereof |
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| CN103588799A (en) * | 2013-12-05 | 2014-02-19 | 南开大学 | Cadmium coordination polymer and preparation method and application thereof |
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