CN105218818A - Functionalization polysulfones-Tb (III) ionic complex luminescent material preparation method - Google Patents
Functionalization polysulfones-Tb (III) ionic complex luminescent material preparation method Download PDFInfo
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Abstract
The invention belongs to bonding type polymer-rare-earth complexes luminous material field, a kind of functionalization polysulfones-Tb (III) ionic complex luminescent material preparation method, at the synthesis of polysulfones side chain and the bidentate Schiff's base aglucon of bonding with coordination chelating and sensitized luminescence dual-use function, this Schiff's base aglucon can with rare earth Tb (III) ion coordination, form stable polymer-rare earth compounding, there is again conjugation aromatic ring, there is very strong absorbing properties, intramolecular energy can be there is significantly, the fluorescent emission of strong sensitization rare earth Tb (III) ion, have successfully been obtained the embedded photoluminescent material of transmitting green light.
Description
Technical field
The invention belongs to bonding type polymer-rare-earth complexes luminous material field, be specifically related to a kind of functionalization polysulfones-Tb (III) ionic complex luminescent material preparation method.
Background technology
In field of light emitting materials, bonding type polymer-rare earth compounding has important using value and development prospect.Such material not only remains the unique and luminescent properties of excellence of small molecules rare earth compounding, also there is the excellent mechanical property of macromolecular compound and the feature (being particularly easy to the characteristic of film forming) being easy to machine-shaping, and compared with being doped in small molecules rare earth compounding the luminescent material that polymeric matrix formed, bonding type polymer-rare-earth complexes luminous material presents the speciality of inner homogeneous phase, and these characteristics are all extremely conducive to its practical application.
Prepare bonding type polymer-rare earth compounding and have two kinds of basic modes, or obtain (YanCH by the polyreaction of the rare earth compounding containing polymerizable double bond, HuHH, XuCJ, ZhuW, ZhangM, BuXR.JournalofPhotochemistryandPhotobiologyA:Chemistry, 2009,204:19.), or form (LiuD by the aglucon on polymer macromolecule chain and rare-earth ion coordination, WangZG, YuH, YouJ.EuropeanPolymerJournal, 2009,45:2260).Preparation is often more difficult containing the monomer of rare earth compounding, and the molecular weight of polymerization products therefrom is limited; And first small molecules aglucon is bonded in polymer lateral chain (or on original copolymer side chain just containing aglucon) by macromolecular reaction and forms macromolecular ligand, then make it to form bonding type polymer-rare earth compounding with rare-earth ion coordination, this compares a kind of method being easy to carry out again.But, in the bonding type polymer-rare-earth complexes luminous material system reported, the aglucon majority participating in coordination in polymer lateral chain is fat carboxyl (mainly coming from monomeric acrylic or methacrylic acid), fat carboxyl only plays coordination chelating to rare earth ion, without sensitization (i.e. " Antenna " effect) function, need to add the isosteric smaller ligand of association, luminous material (SuoQl could be formed, LuF, ShiJW, HongHL, LuoJP.JournalofRareEarths, 2009, 27:28), this has limited to the luminescent properties of such functional materials to a great extent.
Summary of the invention
Technical problem to be solved by this invention is: how to provide a kind of preparation method simple, aglucon is with the bonding type polymer-rare earth embedded photoluminescent material of the dual-use function of coordination and sensitization, and this material has the characteristic of excellent mechanical property, the easily transmitting green light of machine-shaping and material internal homogeneous phase.
To manage at polymer lateral chain bonding the aglucon of rare earth ion with coordination chelating and sensitized luminescence dual-use function, be prepare high luminescence can the effective way of polymer-RE compound material.Schiff base compounds is also the important aglucon of a class, they not only can with rare earth ion generation coordination, thus form stable title complex; The more important thing is that Schiff's base aglucon has conjugation aromatic ring mostly, therefore there is very strong absorbing properties, strong intramolecular energy may occur, and therefore, multiple tooth Schiff's base aglucon is also a class with the aglucon of coordination chelating and sensitized luminescence dual-use function.Aldehyde group is bonded in polysulfones side chain by esterification by the present invention, again with 3-aminopyridine for reagent, aldehyde radical and primary amino are rolled into a ball schiff base reaction occurs, thus formed on polysulfones side chain bidentate Schiff's base aglucon (atom N in this aglucon imine structure C=N and pyridine atom N are " bidentate ", make this aglucon can with rare earth ion generation chelating ligands).The polysulfones that this bidentate Schiff's base is ligand functionalized, by the coordination of macromolecular ligand and Tb (III), obtains the schiff's base type polymer-rare earth compounding of transmitting green light.
The technical solution adopted in the present invention is: functionalization polysulfones-Tb (III) ionic complex luminescent material preparation method, carries out according to following step:
Step one, 0.5a gram of chloromethyl polysulphone (CMPSF) is joined 50a milliliter solvent, chloromethyl polysulphone is fully dissolved, then adds oxoethanoic acid (GA) and acid binding agent, under nitrogen protection, constant temperature stirs and esterification occurs, after reaction terminates, add ethanol and product is settled out, suction filtration, with ethanol and distilled water repetitive scrubbing, vacuum-drying, to constant weight, obtains the modified polysulfone PSF-AL of side chain bonding acetaldehyde (AL) group, and a is an arithmetic number;
Step 2, modified polysulfone PSF-AL 0.5b gram step one prepared add 50b milliliter
n, N-after dissolving completely in N,N-DIMETHYLACETAMIDE (DMAC), add the 3-aminopyridine (AP) of 0.05b ~ 0.075b gram, constant temperature in 60 DEG C ~ 70 DEG C, under nitrogen protection and agitation condition, the schiff base reaction between modified polysulfone PSF-AL and 3-aminopyridine is made to carry out 6 ~ 8 hours, after reaction terminates, alcohol settling, filters, with ethanol and distilled water alternately washing, vacuum-drying is to constant weight, and obtain the functionalization polysulfones PSF-AA that side chain is bonded with bidentate Schiff's base (AA) aglucon, b is an arithmetic number;
Step 3, functionalization polysulfones PSF-AA 0.35c gram of step 2 prepared add 50c milliliter
n, N-in N,N-DIMETHYLACETAMIDE amine, add the six trichloride hydrate terbium crystal that mole number is 1/3 of bidentate Schiff's base aglucon AA molar content in functionalization polysulfones PSF-AA again, make it to dissolve, in the water-bath of 60 DEG C, constant temperature stirs, and reacts 10 hours, add precipitation agent ethanol, filter, and after alternately washing with ethanol and distilled water, vacuum-drying is to constant weight, obtaining binary polymer-rare earth compounding PSF-(AA) 3-Tb (III), c is an arithmetic number.
Step 4, binary polymer-rare earth compounding PSF-(AA) 3-Tb (III) step 3 prepared are dissolved in
n, N-in N,N-DIMETHYLACETAMIDE, make Tb
3+ionic concn is 4.0 × 10-5mol/L, obtains functionalization polysulfones-Tb (III) ionic complex luminescent material, uses fluorescence spectrophotometer, and the fluorescence emission spectrum measuring this solution with best excitation peak 278nm place, launches strong green glow.
As a kind of optimal way: in step one, institute's solubilizing agent is N,N-dimethylacetamide or DMF (DMF), and acid binding agent used is Na
2cO
3, consumption is 0.159a ~ 0.191a gram.
As a kind of optimal way: in step one, the cl content of chloromethyl polysulphone is 1.5mmol/g ~ 1.8mmol/g, and the amount of oxoethanoic acid is 0.166 ~ 0.266a gram.
As a kind of optimal way: in step one, the temperature of reaction of esterification is 65 DEG C ~ 85 DEG C, and the reaction times is 8 ~ 12 hours.
A, b, c of more than using are an arithmetic number, in order to the relation between clarity quality and volume is introduced.
The invention has the beneficial effects as follows: the present invention is first at the synthesis of polysulfones side chain and bonding Schiff's base aglucon, the polysulfones that obtained bidentate Schiff's base is ligand functionalized, Schiff's base aglucon is with coordination chelating and sensitized luminescence dual-use function, by with rare earth Tb (III) ion coordination, the schiff's base type polymer-rare earth compounding of transmitting green light can be obtained.This reaction is easily carried out, and obtained schiff's base type polymer-rare earth compounding has the speciality of inner homogeneous phase, has the excellent mechanical property of polysulfones and the feature being easy to machine-shaping concurrently.
The inventive method is at the synthesis of polysulfones side chain and the bidentate Schiff's base aglucon of bonding with coordination chelating and sensitized luminescence dual-use function, Schiff's base aglucon can with rare earth Tb (III) ion coordination, form stable polymer-rare earth compounding, there is again conjugation aromatic ring, there is very strong absorbing properties, significantly intramolecular energy can occur, the fluorescent emission of strong sensitization rare earth Tb (III) ion, have successfully been obtained the embedded photoluminescent material of transmitting green light.
Accompanying drawing explanation
Fig. 1 is the general formula that side chain of the present invention is bonded with the functionalization polysulfones PSF-AA of bidentate Schiff's base aglucon.
Embodiment
Embodiment 1
In the four-hole bottle that prolong, agitator, thermometer are housed, add 0.5g chloromethyl polysulphone (CMPSF) and 50mLN that cl content is 1.6mmol/g, N-N,N-DIMETHYLACETAMIDE (DMAC), makes CMPSF fully dissolve, then adds 0.166g oxoethanoic acid (GA) and 0.159g acid binding agent Na
2cO
3, under nitrogen protection, constant temperature 85 DEG C, stirs and esterification 10h occurs, and after reaction terminates, add ethanol and settled out by product, suction filtration, with ethanol and distilled water repetitive scrubbing, vacuum-drying, to constant weight, obtains the modified polysulfone PSF-AL of side chain bonding acetaldehyde (AL) group.
0.5g modified polysulfone PSF-AL is joined 50mLN, in N-N,N-DIMETHYLACETAMIDE (DMAC) completely dissolve after, add the 3-aminopyridine (AP) of 0.05g, constant temperature in 70 DEG C, N
2protection and agitation condition under; the schiff base reaction between PSF-AL and AP is made to carry out 8h; after reaction terminates; alcohol settling; filter, with ethanol and distilled water alternately washing, vacuum-drying is to constant weight; obtain the functionalization polysulfones PSF-AA that side chain is bonded with bidentate Schiff's base aglucon, the bonded amount of AA is 1.22mmol/g.
0.35g functionalization polysulfones PSF-AA is dissolved in 50mLDMAC, then adds 0.0528g(0.142mmol) six trichloride hydrate terbium crystal, make it to dissolve; In the water-bath of this solution system being put 60 DEG C, constant temperature stirs, reaction 10h; Add precipitation agent ethanol, filter, and after alternately washing with ethanol and distilled water, vacuum-drying, to constant weight, obtains binary polymer-rare earth compounding PSF-(AA)
3-Tb (III).
Deployment and conjugation thing PSF-(AA)
3the DMAC solution of-Tb (III), makes Tb
3+ionic concn is 4.0 × 10
-5mol/L, uses fluorescence spectrophotometer, and the fluorescence emission spectrum measuring this solution with best excitation peak 278nm place, launches strong green glow.
Embodiment 2
In the four-hole bottle that prolong, agitator, thermometer are housed, add 0.5g chloromethyl polysulphone (CMPSF) and 50mL solvent DMAC that cl content is 1.7mmol/g, CMPSF is fully dissolved.Add 0.266g oxoethanoic acid (GA) and 0.19g acid binding agent Na again
2cO
3, N
2under protection, constant temperature 65 DEG C, stirs and esterification 8h occurs.After reaction terminates, add ethanol and settled out by product, suction filtration, with ethanol and distilled water repetitive scrubbing, vacuum-drying, to constant weight, obtains the modified polysulfone PSF-AL of side chain bonding acetaldehyde (AL) group.After being dissolved completely by 0.5g modified polysulfone PSF-AL and 50mL solvent DMAC, add the 3-aminopyridine (AP) of 0.065g, constant temperature in 60 DEG C, N
2protect and under agitation condition, make the schiff base reaction between PSF-AL and AP carry out 7h.After reaction terminates, alcohol settling, filters, and with ethanol and distilled water alternately washing, vacuum-drying is to constant weight, and obtain the functionalization polysulfones PSF-AA that side chain is bonded with bidentate Schiff's base aglucon, the bonded amount of AA is 1.26mmol/g.0.35g functionalization polysulfones PSF-AA is dissolved in 50mLDMAC, then adds 0.0546g(0.147mmol) six trichloride hydrate terbium crystal, make it to dissolve; In the water-bath of this solution system being put 60 DEG C, constant temperature stirs, reaction 10h; Add precipitation agent ethanol, filter, and after alternately washing with ethanol and distilled water, vacuum-drying, to constant weight, obtains binary polymer-rare earth compounding PSF-(AA)
3-Tb (III).Deployment and conjugation thing PSF-(AA)
3the DMAC solution of-Tb (III), makes Tb
3+ionic concn is 4.0 × 10
-5mol/L, uses fluorescence spectrophotometer, and the fluorescence emission spectrum measuring this solution with best excitation peak 278nm place, launches strong green glow.
Embodiment 3
In the four-hole bottle that prolong, agitator, thermometer are housed, add 0.5g chloromethyl polysulphone (CMPSF) and 50mL solvent DMAC that cl content is 1.8mmol/g, CMPSF is fully dissolved.Add 0.233g oxoethanoic acid (GA) and 0.19g acid binding agent Na again
2cO
3, N
2under protection, constant temperature 75 DEG C, stirs and esterification 12h occurs.After reaction terminates, add ethanol and settled out by product, suction filtration, with ethanol and distilled water repetitive scrubbing, vacuum-drying, to constant weight, obtains the modified polysulfone PSF-AL of side chain bonding acetaldehyde (AL) group.After being dissolved completely by 0.5g modified polysulfone PSF-AL and 50mL solvent DMAC, add the 3-aminopyridine (AP) of 0.075g, constant temperature in 70 DEG C, N
2protect and under agitation condition, make the schiff base reaction between PSF-AL and AP carry out 8h.After reaction terminates, alcohol settling, filters, and with ethanol and distilled water alternately washing, vacuum-drying is to constant weight, and obtain the functionalization polysulfones PSF-AA that side chain is bonded with bidentate Schiff's base aglucon, the bonded amount of AA is 1.3mmol/g.0.35g functionalization polysulfones PSF-AA is dissolved in 50mLDMAC, then adds 0.0563g(0.152mmol) six trichloride hydrate terbium crystal, make it to dissolve; In the water-bath of this solution system being put 60 DEG C, constant temperature stirs, reaction 10h; Add precipitation agent ethanol, filter, and after alternately washing with ethanol and distilled water, vacuum-drying, to constant weight, obtains binary polymer-rare earth compounding PSF-(AA)
3-Tb (III).Deployment and conjugation thing PSF-(AA)
3the DMAC solution of-Tb (III), makes Tb
3+ionic concn is 4.0 × 10
-5mol/L, uses fluorescence spectrophotometer, and the fluorescence emission spectrum measuring this solution with best excitation peak 278nm place, launches strong green glow.
Embodiment 4
In the four-hole bottle that prolong, agitator, thermometer are housed, add 0.5g chloromethyl polysulphone (CMPSF) and 50mL solvent DMF that cl content is 1.5mmol/g, CMPSF is fully dissolved.Add 0.22g oxoethanoic acid (GA) and 0.17g acid binding agent Na again
2cO
3, N
2under protection, constant temperature 75 DEG C, stirs and esterification 12h occurs.After reaction terminates, add ethanol and settled out by product, suction filtration, with ethanol and distilled water repetitive scrubbing, vacuum-drying, to constant weight, obtains the modified polysulfone PSF-AL of side chain bonding acetaldehyde (AL) group.After being dissolved completely by 0.5g modified polysulfone PSF-AL and 50mL solvent DMAC, add the 3-aminopyridine (AP) of 0.075g, constant temperature in 70 DEG C, N
2protect and under agitation condition, make the schiff base reaction between PSF-AL and AP carry out 8h.After reaction terminates, alcohol settling, filters, and with ethanol and distilled water alternately washing, vacuum-drying is to constant weight, and obtain the functionalization polysulfones PSF-AA that side chain is bonded with bidentate Schiff's base aglucon, the bonded amount of AA is 1.24mmol/g.0.35g functionalization polysulfones PSF-AA is dissolved in 50mLDMAC, then adds 0.0537g(0.124mmol) six trichloride hydrate terbium crystal, make it to dissolve; In the water-bath of this solution system being put 60 DEG C, constant temperature stirs, reaction 10h; Add precipitation agent ethanol, filter, and after alternately washing with ethanol and distilled water, vacuum-drying, to constant weight, obtains binary polymer-rare earth compounding PSF-(AA)
3-Tb (III).Deployment and conjugation thing PSF-(AA)
3the DMAC solution of-Tb (III), makes Tb
3+ionic concn is 4.0 × 10
-5mol/L, uses fluorescence spectrophotometer, and the fluorescence emission spectrum measuring this solution with best excitation peak 278nm place, launches strong green glow.
Embodiment 5
In the four-hole bottle that prolong, agitator, thermometer are housed, add 0.5g chloromethyl polysulphone (CMPSF) and 50mL solvent DMF that cl content is 1.7mmol/g, CMPSF is fully dissolved.Add 0.22g oxoethanoic acid (GA) and 0.17g acid binding agent Na again
2cO
3, N
2under protection, constant temperature 70 DEG C, stirs and esterification 10h occurs.After reaction terminates, add ethanol and settled out by product, suction filtration, with ethanol and distilled water repetitive scrubbing, vacuum-drying, to constant weight, obtains the modified polysulfone PSF-AL of side chain bonding acetaldehyde (AL) group.After being dissolved completely by 0.5g modified polysulfone PSF-AL and 50mL solvent DMAC, add the 3-aminopyridine (AP) of 0.055g, constant temperature in 65 DEG C, N
2protect and under agitation condition, make the schiff base reaction between PSF-AL and AP carry out 7h.After reaction terminates, alcohol settling, filters, and with ethanol and distilled water alternately washing, vacuum-drying is to constant weight, and obtain the functionalization polysulfones PSF-AA that side chain is bonded with bidentate Schiff's base aglucon, the bonded amount of AA is 1.2mmol/g.0.35g functionalization polysulfones PSF-AA is dissolved in 50mLDMAC, then adds 0.052g(0.14mmol) six trichloride hydrate terbium crystal, make it to dissolve; In the water-bath of this solution system being put 60 DEG C, constant temperature stirs, reaction 10h; Add precipitation agent ethanol, filter, and after alternately washing with ethanol and distilled water, vacuum-drying, to constant weight, obtains binary polymer-rare earth compounding PSF-(AA)
3-Tb (III).Deployment and conjugation thing PSF-(AA)
3the DMAC solution of-Tb (III), makes Tb
3+ionic concn is 4.0 × 10
-5mol/L, uses fluorescence spectrophotometer, and the fluorescence emission spectrum measuring this solution with best excitation peak 278nm place, launches strong green glow.
Claims (4)
1. functionalization polysulfones-Tb (III) ionic complex luminescent material preparation method, is characterized in that carrying out according to following step:
Step one, 0.5a gram of chloromethyl polysulphone is joined 50a milliliter solvent, chloromethyl polysulphone is fully dissolved, then adds oxoethanoic acid and acid binding agent, under nitrogen protection, constant temperature stirs and esterification occurs, after reaction terminates, add ethanol and product is settled out, suction filtration, with ethanol and distilled water repetitive scrubbing, vacuum-drying, to constant weight, obtains the modified polysulfone PSF-AL of side chain bonding aldehyde group, and a is an arithmetic number;
Step 2, modified polysulfone PSF-AL 0.5b gram step one prepared add 50b milliliter
n, N-after dissolving completely in N,N-DIMETHYLACETAMIDE, add the 3-aminopyridine of 0.05b ~ 0.075b gram, constant temperature in 60 DEG C ~ 70 DEG C, under nitrogen protection and agitation condition, the schiff base reaction between modified polysulfone PSF-AL and 3-aminopyridine is made to carry out 6 ~ 8 hours, after reaction terminates, alcohol settling, filters, with ethanol and distilled water alternately washing, vacuum-drying is to constant weight, and obtain the functionalization polysulfones PSF-AA that side chain is bonded with bidentate Schiff's base aglucon, b is an arithmetic number;
Step 3, functionalization polysulfones PSF-AA 0.35c gram of step 2 prepared add 50c milliliter
n, N-in N,N-DIMETHYLACETAMIDE, add the six trichloride hydrate terbium crystal that mole number is 1/3 of bidentate Schiff's base aglucon AA molar content in functionalization polysulfones PSF-AA again, make it to dissolve, in the water-bath of 60 DEG C, constant temperature stirs, and reacts 10 hours, add precipitation agent ethanol, filter, and after alternately washing with ethanol and distilled water, vacuum-drying is to constant weight, obtaining binary polymer-rare earth compounding PSF-(AA) 3-Tb (III), c is an arithmetic number;
Step 4, binary polymer-rare earth compounding PSF-(AA) 3-Tb (III) step 3 prepared are dissolved in
n, N-in N,N-DIMETHYLACETAMIDE, make Tb
3+ionic concn is 4.0 × 10-5mol/L, obtains functionalization polysulfones-Tb (III) ionic complex luminescent material.
2. functionalization polysulfones-Tb (III) ionic complex luminescent material preparation method according to claim 1, it is characterized in that: in step one, institute's solubilizing agent is N,N-dimethylacetamide or DMF, acid binding agent used is Na
2cO
3, consumption is 0.159a ~ 0.191a gram.
3. functionalization polysulfones-Tb (III) ionic complex luminescent material preparation method according to claim 1, it is characterized in that: in step one, the cl content of chloromethyl polysulphone is 1.5mmol/g ~ 1.8mmol/g, and the amount of oxoethanoic acid is 0.166 ~ 0.266a gram.
4. functionalization polysulfones-Tb (III) ionic complex luminescent material preparation method according to claim 1, is characterized in that: in step one, the temperature of reaction of esterification is 65 DEG C ~ 85 DEG C, and the reaction times is 8 ~ 12 hours.
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