CN109942831A - Two kinds of photochromic purpurine Subjective and Objective MOFs materials and its preparation and application - Google Patents
Two kinds of photochromic purpurine Subjective and Objective MOFs materials and its preparation and application Download PDFInfo
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Abstract
The present invention relates to the synthesis fields of purpurine MOFs off-color material, specifically based on intermolecular electronics transfer based on three-dimensional anion MOFs, alkyl viologen be object off-color material and its preparation and application.Its chemical formula is { (EV)0.5[Cd(BTC)(H2O)]·2H2O}nOr { (PV)0.5[Cd(BTC)(H2O)]·2H2O}n, the EV2+For (1,1- bis- (ethyl) -4,4- bipyridine cation), the PV2+For 1,1- bis- (propyl) -4,4- bipyridine cation.Two kinds of purpurine Subjective and Objective MOFs photochromic materials are provided using double ethyl purpurine cations, double propyl purpurines cation and carboxylic acid-Cd anion MOFs skeleton as electron acceptor and donor respectively in the present invention.Preparation method is simple for purpurine Subjective and Objective MOFs off-color material provided by the invention, economical nontoxic.
Description
Technical field
The present invention relates to the synthesis fields of purpurine MOFs off-color material, specifically based on intermolecular electronics transfer with three-dimensional
Based on anion MOFs, alkyl viologen is off-color material and its preparation and application of object.
Background technique
Metal organic frame (Metal-Organic Frameworks, MOFs) is one kind by organic ligand and metal center
Combine obtained hybrid inorganic-organic materials with molecule internal pore through coordinate bond, unique network topology structure and its
There is potential application prospect in multiple fields and become one of the hot spot that scientific worker studies.Different bases are synthesized by design
The organic ligand of group's modification has the function of that the MOFs material of different performance becomes MOFs in this year investigation of materials purposefully to construct
Important channel.
In recent years, due to the easy modified and high charge of viologen compound (1,1- disubstituted 4,4- dipyridyl derivatives)
Separating degree occurs electronics transfer under the stimulation of light or electricity and generates different redox states, and it is between different conditions
Reversible transition can often induce the rule variation of other light, electricity, magnetic property.How using purpurine as functional group introducing MOFs, structure
Building MOFs material is significantly to study.
Summary of the invention
The present invention is intended to provide a kind of be based on based on three-dimensional anion MOFs, alkyl viologen is the photochromic material of object
Material.
The present invention is achieved by the following technical solutions: purpurine Subjective and Objective MOFs material, and chemical formula is { (EV)0.5
[Cd(BTC)(H2O)]·2H2O}nOr { (PV)0.5[Cd(BTC)(H2O)]·2H2O}n, the EV2+For (1,1- bis- (ethyl) -4,
4- bipyridine cation), the PV2+For 1,1- bis- (propyl) -4,4- bipyridine cation, structural formula are as follows:
Wherein R is-CH2CH3Or-CH2CH2CH3, BTC is (C9H3O6)3-。
As the further improvement of technical solution of the present invention, it is mono- that the crystal of the material passes through Bruker D8Venture
Brilliant diffractometer is measured, and is radiated with graphite monochromator Mo-K αData are collected with ω scanning mode, are gone forward side by side
Row Lp factor correction and SADABS program absorption correction, analytic structure determine the position of heavy atom using direct method, then with poor
Value function method and least square method find out non-hydrogen atom coordinate, and obtain the position of hydrogen atom with theoretical hydrogenation method, with minimum two
Multiplication is modified structure, and all non-hydrogen atoms are all by anisotropy；All calculating work Olex2 and ShelXL programs
It completes；It is as follows to measure crystallographic parameter difference: molecular weight 480.71 belongs to monoclinic system, space group P21/C, cell parameterα (°)=90, β (°)=106.2820 (10),
γ (°)=90,Z=4；Molecular weight is 494.74, belongs to monoclinic system, space group P21/C, cell parameterα (°)=90, β (°)=105.8260, γ (°)=
90,Z=4.
Invention further provides the purpurine Subjective and Objective MOFs materials to become as photochromic and photo-induced reversible
Application in color material.
Illustrate technical solution of the present invention in order to clearer, invention further provides the purpurine Subjective and Objectives
The preparation method of MOFs material, comprising the following steps:
1) 4,4- bipyridyl, bromoethane are heated to reflux 24 hours according to molar ratio 1:2 in the solvent of anhydrous acetonitrile, it is cold
But, it filters, is rinsed with acetonitrile, obtain the alkyl viologen ligand 1 of faint yellow solid powder, 1- bis- (ethyl) -4,4- bipyridyl bromine
Salt dissolving；Wherein bromoethane obtains the alkyl viologen ligand 1 of faint yellow solid powder, 1- bis- (propyl)-after being substituted for 3- N-Propyl Bromide
4,4- bipyridyl Bromide；
2) by alkyl viologen ligand, 1:2 is dissolved in deionized water in molar ratio with cadmium nitrate；
3) 1,3,5- trimesic acid, NaOH are dissolved in deionized water according to molar ratio 1:3 heating；
4) above two solution being mixed, is placed at room temperature for 5 days, crystal is precipitated, and is washed with water, and it is dry, obtain colourless bulk
The purpurine Subjective and Objective MOFs material of crystal.
Invention further provides the preparation flows of above two purpurine Subjective and Objective MOFs material:
Wherein, R is-CH2CH3Or-CH2CH2CH3, BTC is (C9H3O6)3-.Anion [the Cd (BTC) of the material
(H2O)]-It is three-dimensional anion MOFs for electron donor；Purpurine cation is electron acceptor.
The preparation method of purpurine Subjective and Objective MOFs material provided by the present invention uses aqueous solution as solvent, economic nothing
Poison, environmental protection.
Two kinds of purpurine Subjective and Objective MOF of the present invention have the advantage that relative to existing off-color material
(1) respectively with double ethyl purpurine cations, double propyl purpurines cation and carboxylic acid-Cd anion MOFs in the present invention
Skeleton is electron acceptor and donor, provides two kinds of purpurine Subjective and Objective MOFs photochromic materials.
(2) a kind of off-color material provided by the invention based on intermolecular electronics transfer can occur under ultraviolet light
Ability of reverse photochromism, and obtain a kind of long lived photo induced charge separation crystalline material.
(3) preparation method is simple for purpurine Subjective and Objective MOFs off-color material provided by the invention, economical nontoxic.
Detailed description of the invention
In order to more clearly explain the embodiment of the invention or the technical proposal in the existing technology, to embodiment or will show below
There is attached drawing needed in technical description to be briefly described, it should be apparent that, the accompanying drawings in the following description is only this
Some embodiments of invention for those of ordinary skill in the art without creative efforts, can be with
It obtains other drawings based on these drawings.
Fig. 1 is the unsymmetric structure primitive figure of two kinds of purpurine Subjective and Objectives MOFs according to the present invention.
Fig. 2 is the anion MOFs structure chart of two kinds of purpurine Subjective and Objectives MOFs according to the present invention.
Fig. 3 is the packed structures figure of two kinds of purpurine Subjective and Objectives MOFs according to the present invention.
Fig. 4 is the light-induced variable chromatic graph of two kinds of purpurine Subjective and Objective MOFs according to the present invention.
Fig. 5 is the EPR map of the photochromic front and back two kinds of purpurine Subjective and Objectives MOFs according to the present invention.It can be seen by figure
Out: after illumination, compound 1 and 2 produces strong Free Radical Signal (g=2.0029).It is indicated above that in ultraviolet irradiation condition
Under, it is the photochromic of electronics transfer that color change, which not only occurs, for two kinds of compounds, but also produces a large amount of purpurine free radical
Behavior.
Fig. 6 is the PXRD map of the photochromic front and back two kinds of purpurine Subjective and Objectives MOFs according to the present invention.It can be with by figure
Find out: before and after illumination, there is no significantly changing for the PXRD map of compound 1 and 2.It is indicated above that the light of two kinds of compounds
Mutagens color behavior is not caused by the isomerization as caused by illumination or decomposition.
Fig. 7 is the UV-vis absorption spectrum of the photochromic front and back two kinds of purpurine Subjective and Objectives MOFs according to the present invention.By
For figure it can be seen that after illumination, there are two characteristic absorption peaks (416nm and 620nm) in the ultraviolet spectra of compound 1 and 2, this and purple
The absorption peak of smart free radical coincide, and further demonstrates that, the discoloration behavior of two kinds of compounds is by generating purpurine free radical after illumination
The photochromic behavior of caused electronics transfer.
Specific embodiment
To make the object, technical solutions and advantages of the present invention clearer, technical solution of the present invention will be carried out below
Detailed description.Obviously, described embodiments are only a part of the embodiments of the present invention, instead of all the embodiments.Base
Embodiment in the present invention, those of ordinary skill in the art are obtained all without making creative work
Other embodiment belongs to the range that the present invention is protected.
Technical solution of the present invention is described in detail with reference to the accompanying drawing.
Embodiment 1
4,4- bipyridyl (1.56mg, 0.01mol) and bromoethane (2mL, 0.027mol) are added to 30mL acetonitrile solution
In, after being heated to reflux 24 hours, faint yellow turbid is obtained, cooling, filtering is dry after being washed with acetonitrile, purpurine ligand 1 is obtained,
1- bis- (ethyl) -4,4- bipyridyl Bromide.Yield: 88.3% (being based on 4,4- bipyridyl).
Embodiment 2
It is molten that 4,4- bipyridyl (1.56mg, 0.01mol) and 1- N-Propyl Bromide (2mL, 0.022mol) are added to 30mL acetonitrile
In liquid, after being heated to reflux 24 hours, faint yellow turbid is obtained, cooling, filtering is dry after being washed with acetonitrile, obtains purpurine ligand
1,1- bis- (propyl) -4,4- bipyridyl Bromide.Yield: 87.6% (being based on 4,4- bipyridyl).
Embodiment 3
By 1,1- bis- (ethyl) -4,4- bipyridyl Bromide (187mg, 0.50mmol) and Cd (NO3)2·4H2O (309mg,
It 1.0mmol) is added in 20.00mL deionized water solution, stirring after ten minutes, obtains clear solution；By the equal benzene three of 1,3,5-
Sour (210mg, 1.0mmol) and NaOH (120mg, 3.0mmol) are added in 30.00mL deionized water solution, heating stirring 10
After minute, clear solution is obtained；Above two solution is mixed, stirs, obtains a little turbid solution, cooling, filtering obtains clear
Clear solution is slowly volatilized at room temperature, obtains colourless bulk crystals (compound 1), dry after being washed with acetonitrile.Yield: 34.7%
(being based on Cd).
Embodiment 4
By 1,1- bis- (propyl) -4,4- bipyridyl Bromide (201mg, 0.50mmol) and Cd (NO3)2·4H2O (309mg,
It 1.0mmol) is added in 20.00mL deionized water solution, stirring after five minutes, obtains clear solution；By 1,3,5- trimesic acid
(210mg, 1.0mmol) and NaOH (120mg, 3.0mmol) are added in 30mL deionized water solution, and heating stirring 10 minutes
Afterwards, clear solution is obtained；Above two solution is mixed, stirs, obtains a little turbid solution, cooling, filtering obtains clarifying molten
Liquid slowly volatilizees at room temperature, obtains colourless bulk crystals (compound 2), dry after being washed with acetonitrile.Yield: 30.4% (is based on
Cd)。
Embodiment 5 is photic and reversible color is tested
Photochromic experiment: light source used is the high-pressure sodium lamp (~365nm) of 175W, the list for the compound 1 that will be singled out
Crystalline substance is placed on sheet glass, and sheet glass is placed on the thermostat metal plate away from light source 20cm, is irradiated after twenty minutes, compound 1
Crystal color gradually becomes light blue by colourless, reaches saturation within 60 minutes, the light blue crystal after discoloration is designated as 1P.In dark
After the 2 day time of middle placement, their color reverts to colourless (1D) originally completely again.This-the reversible change of colour killing of adding lustre to
At least 5 times can be recycled, stability with higher.
The photochromic experiment of embodiment 6
Photochromic experiment: light source used is the high-pressure sodium lamp (~365nm) of 175W, the list for the compound 2 that will be singled out
Crystalline substance is placed on sheet glass, and sheet glass is placed on the thermostat metal plate away from light source 20cm, after irradiation 15 minutes, compound 2
Crystal color gradually becomes blue by colourless, reaches saturation within 60 minutes, and the blue colored crystal after discoloration is designated as 2P.It puts in the dark
After setting 7 day time, their color reverts to colourless (2D) originally completely again.It is this add lustre to-reversible change of colour killing can be with
Circulation at least 5 times, stability with higher.
Embodiment 7
It is the crystal structure determination for the compound 1 and 2 that embodiment 3 and embodiment 4 obtain is as follows: to pick out under the microscope
The monocrystalline of suitable dimension carries out x-ray crystal structure analysis.The X ray diffracting data of crystal uses Bruker D8Venture
Single crystal diffractometer measurement, is radiated with graphite monochromator Mo-K αData are collected with ω scanning mode, and are carried out
Lp factor correction and SADABS program absorption correction.Analytic structure determines the position of heavy atom using direct method, then uses difference
Function method and least square method find out non-hydrogen atom coordinate, and obtain the position of hydrogen atom with theoretical hydrogenation method, use least square
Method is modified structure, and all non-hydrogen atoms are all by anisotropy.All calculating work are complete with Olex2 and ShelXL program
At.Compound predominant crystal data is shown in Table 1.
The 1. crystallographic structure parameter of compound 1 and 2 of table
aR1=∑ | | Fo|-|Fc||/∑|Fo|,bwR2=[∑ w (Fo 2-Fc 2)2/∑w(Fo 2)2]1/2
The above description is merely a specific embodiment, but scope of protection of the present invention is not limited thereto, any
Those familiar with the art in the technical scope disclosed by the present invention, can easily think of the change or the replacement, and should all contain
Lid is within protection scope of the present invention.Therefore, protection scope of the present invention should be based on the protection scope of the described claims.
Claims (5)
1. purpurine Subjective and Objective MOFs material, which is characterized in that its chemical formula is { (EV)0.5[Cd(BTC)(H2O)]·2H2O}n Or
{(PV)0.5[Cd(BTC)(H2O)]·2H2O}n, the EV2+It is described for (1,1- bis- (ethyl) -4,4- bipyridine cation)
PV2+For 1,1- bis- (propyl) -4,4- bipyridine cation, structural formula are as follows:
, wherein R is-CH2CH3Or-CH2CH2CH3, BTC is (C9H3O6)3-。
2. purpurine Subjective and Objective MOFs material according to claim 1, which is characterized in that the crystal of the material passes through
Bruker D8 Venture single crystal diffractometer is measured, and is radiated with graphite monochromator Mo-K α, and λ=0.71073,
Data are collected with ω scanning mode, and carry out Lp factor correction and SADABS program absorption correction, analytic structure uses direct
Method determines the position of heavy atom, then finds out non-hydrogen atom coordinate with difference function method and least square method, and add hydrogen with theory
Method obtains the position of hydrogen atom, is modified with least square method to structure, all non-hydrogen atoms are all by anisotropy；It is all
Work is calculated to be completed with Olex2 and ShelXL program；It is as follows to measure crystallographic parameter difference: molecular weight 480.71 belongs to single
Oblique system, space groupP2 1/ c, cell parametera ()=10.2125 (7),b()=11.7849 (8),c (Å) =
15.0287 (10),α(°)=90,β(°)=106.2820 (10),γ(°)=90,V (Å3)=1736.2 (2),Z =
4；Molecular weight is 494.74, belongs to monoclinic system, space groupP2 1/ c, cell parametera ()=10.1781 (7),b (Å) =
12.2779 (8),c()=14.9454 (10),α(°)=90,β(°)=105.8260,γ(°)=90,V (Å3)
=1796.9 (2),Z =4。
3. purpurine Subjective and Objective MOFs material of any of claims 1 or 2 is as in photochromic and photo-induced reversible off-color material
Application.
4. the preparation method of purpurine Subjective and Objective MOFs material of any of claims 1 or 2, which comprises the following steps:
1) 4,4- bipyridyl, bromoethane are heated to reflux 24 hours according to molar ratio 1:2 in the solvent of anhydrous acetonitrile, it is cooling,
Filtering, is rinsed with acetonitrile, obtains the alkyl viologen ligand 1 of faint yellow solid powder, 1- bis- (ethyl) -4,4- bipyridyl bromination
Salt；Wherein bromoethane, which is substituted for after 3- N-Propyl Bromide, obtains the alkyl viologen ligand 1 of faint yellow solid powder, 1- bis- (propyl) -4,
4- bipyridyl Bromide；
2) by alkyl viologen ligand, 1:2 is dissolved in deionized water in molar ratio with cadmium nitrate；
3) 1,3,5- trimesic acid, NaOH are dissolved in deionized water according to molar ratio 1:3 heating；
4) above two solution being mixed, is placed at room temperature for 5 days, crystal is precipitated, and is washed with water, and it is dry, obtain colourless bulk crystals
Purpurine Subjective and Objective MOFs material.
5. the purpurine Subjective and Objective MOFs material that the preparation method of purpurine Subjective and Objective MOFs material as claimed in claim 4 is prepared
As the application in photochromic and photo-induced reversible off-color material.
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| CN112940271A (en) * | 2021-02-03 | 2021-06-11 | 山西师范大学 | Phenyl diimide based zinc coordination polymer and preparation method and application thereof |
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| CN110372880A (en) * | 2019-08-01 | 2019-10-25 | 淮阴师范学院 | A kind of organic supermolecular photochromic compound and preparation method thereof can be used for two-dimension code anti-counterfeit |
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| CN110305148B (en) * | 2019-08-01 | 2022-02-08 | 淮阴师范学院 | Host-guest Cd (II) photochromic coordination polymer for two-dimensional code anti-counterfeiting and preparation method thereof |
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| CN112940271A (en) * | 2021-02-03 | 2021-06-11 | 山西师范大学 | Phenyl diimide based zinc coordination polymer and preparation method and application thereof |
| CN112940271B (en) * | 2021-02-03 | 2022-07-05 | 山西师范大学 | Phenyl diimide based zinc coordination polymer and preparation method and application thereof |
| CN115353634A (en) * | 2021-11-02 | 2022-11-18 | 渤海大学 | Viologen nickel complex modified octamolybdate crystalline material, synthesis method and application |
| CN115353634B (en) * | 2021-11-02 | 2023-11-07 | 渤海大学 | Octamolybdate crystalline material modified based on viologen nickel complex, synthesis method and application |
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