CN105778090A - Hyperbranched metal phthalocyanine oligomer containing imide structure and preparation method thereof - Google Patents
Hyperbranched metal phthalocyanine oligomer containing imide structure and preparation method thereof Download PDFInfo
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- CN105778090A CN105778090A CN201610333115.1A CN201610333115A CN105778090A CN 105778090 A CN105778090 A CN 105778090A CN 201610333115 A CN201610333115 A CN 201610333115A CN 105778090 A CN105778090 A CN 105778090A
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/0666—Polycondensates containing five-membered rings, condensed with other rings, with nitrogen atoms as the only ring hetero atoms
- C08G73/0672—Polycondensates containing five-membered rings, condensed with other rings, with nitrogen atoms as the only ring hetero atoms with only one nitrogen atom in the ring
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- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
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- C07—ORGANIC CHEMISTRY
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- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
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Abstract
The invention discloses a hyperbranched metal phthalocyanine oligomer containing an imide structure and a preparation method thereof and belongs to the technical field of high polymer materials and preparation thereof. The invention aims at solving the problems that existing hyperbranched phthalocyanine can obviously lower thermal decomposition temperature and conjugation degree of a phthalocyanine polymer and an adverse effect is produced to properties of a material. The preparation method comprises the following steps of: carrying out reaction on 4-amino phthalonitrile and acid anhydride monomers to obtain a tetracyano-terminated monomer containing the imide structure, and then carrying out polymerization reaction to obtain the hyperbranched metal phthalocyanine oligomer containing the imide structure. The prepared hyperbranched metal phthalocyanine oligomer containing the imide structure is obviously improved in third-order nonlinear optical property and thermal stability, integrates a high-performance structure and a functional polymer into a whole and is hopeful to become an ideal material for optical devices.
Description
Technical field
The invention belongs to macromolecular material and preparing technical field thereof, be specifically related to a kind of hyperbranched containing imide structure
Metal phthalocyanine oligomer and preparation method thereof.
Background technology
Nonlinear optical material is that gradually grown up after the appearance of nineteen sixty First laser instrument is brand-new
Subject, through the development of more than 50 years, nonlinear optical material was increasingly becoming one of popular research topic of photoelectric field, its
Light is reconciled the fields such as system, image procossing, all-optical switch, light storage, optical-fibre communications and is all had the development prospect of great potential.From
For in theory, all substances all possess third order non-linear optical property, and the molecule of component and atom are all by positively charged
Atomic nucleus and electronegative electronics constitute.The generation of Third-order nonlinearity is analyzed from microcosmic angle, and material receives
Light irradiates, and the center of its positive and negative charge can occur relative movement, produces the dipole of mutually concussion, induces electric dipole moment
Electric polarization field.The essence of third-order nonlinear optical effect is exactly medium produced third-order non-linear polarization under high light effect
All effects that intensity is caused.Because the difference of optical electric field combination frequency has the different forms of expression, thus can present
Different third-order nonlinear optical effect: include triple-frequency harmonics, f our-wave mixing, two-photon absorption, stimulated Raman scattering, saturated and counter satisfy
With absorption, optical Kerr effect etc..For different Third-order Nonlinear Optical Properties, various optical application devices should
Transport and give birth to.
Phthalocyanine is the big conjugate planes structural compounds with 18 pi-electrons that carbon nitrogen is alternately formed by connecting, and electron cloud divides
Cloth is visibly homogeneous, and C-H bond length is almost identical, and in molecule, the morphotropism of four phenyl ring is minimum, imparts phthalocyanine-like compound pole
Strong chemical stability is the most high temperature resistant, dissolubility resistent etc..It is subject in various fields such as catalysis, conduction, energy reserve, optics
Pay close attention to widely and study, become one of functional material the most most with prospects already.The two dimension of its uniqueness is big altogether
Yoke π-electron system, symmetrical structure result in phthalocyanine compound and possess big nonlinear optical coefficients and quickly photoelectric respone
Time, at " nova " risen up slowly in nonlinear optical material field, have vast potential for future development.Phthalocyanine compound
In, the focus of hyperbranched phthalocyanine always research, highly branched three-dimensional molecular structure imparts the unique physics of phthalocyanine and change
Learn character such as dissolubility, low viscosity, molecular entanglement and big conjugated structure etc., high dielectric material, electron transport material,
The various fields such as dyestuff temperature-sensitive battery, optical nonlinearity material have all carried out substantial amounts of research.But the hyperbranched phthalein of report at present
Cyanines are polyarylether class oligomer, and result shows heat decomposition temperature and the conjugated degree that can substantially reduce phthalocyanine polymer, to material
The performance of material adversely affects.
Imide structure, as the basic structure of excellent engineering plastics polyimides, possesses a lot of excellent character example
Such as fabulous heat stability, high mechanical properties, resistance to irradiation etc., the in addition atom such as the conjugated structure of acid imide self and N, O
Lone electron pair connect can form conjugated polymer, be conducive to improve molecular structure conjugated degree.Imide structure is not only
Being applied to the development work of polyimides thermodynamic material, the modification being simultaneously also widely used for other materials molecular structure is ground
Study carefully.Introduce excellent imide structure and be favorably improved raw-material macroscopic property, the conjugated structure of cyclic imide self
Also development potentiality is had much at dielectric, non-linear optical field.
If hyperbranched phthalocyanine is combined with imido feature, hyperbranched phthalocyanine is tied with acid imide
Structure is combined as basic ideas, by being incorporated into by imide structure in hyperbranched phthalocyanine oligomer, may obtain a kind of heat
Stability is high, nonlinear third order optical susceptibility high, the preferable third order non-linear optical material of excellent performance to be to solve existing fragrance
The hyperbranched phthalocyanine of the same clan is to heat stability and the adverse effect of conjugation.
Summary of the invention
Heat decomposition temperature and the conjugated degree of phthalocyanine polymer can be substantially reduced in order to solve existing hyperbranched phthalocyanine, right
The problem that the performance of material has a negative impact, the invention provides a kind of hyperbranched metal phthalocyanine oligomerisation containing imide structure
Thing and preparation method thereof.
A kind of hyperbranched metal phthalocyanine oligomer containing imide structure in the present invention, its molecular structure is as follows:
In logical formula I,
Me is transition metal ions, preferably Zn2+、Cu+、Ni2+。
Number-average molecular weight Mn of this polymer is 4000～20000g/mol, and molecular weight distribution is 1.03～1.12.
The non-linear absorption coefficient α of this polymer2For (2.4～8.2) × 10-12m W-1, nonlinear viscoelastic piles n2For
(3.9～5.9) × 10-19m-2W, third-order nonlinear optical coefficient χ(3)For (3.2～5.2) × 10-13esu。
The preparation method of the hyperbranched metal phthalocyanine oligomer containing imide structure, specifically comprises the following steps that
Step one, the preparation of four cyano capping monomer containing imide structure
4-amino phthalonitrile is dissolved in dry dimethyl sulfoxide solvent be placed in container, is passed through dry nitrogen
Adding anhydride monomers after gas, quickly after stirring reaction 30～60min, the mixing adding acetic anhydride and pyridine in reaction system is molten
Liquid (volume ratio 5:4), rising temperature of reaction system, to 60～80 DEG C, reacts 10～12 hours.Reaction is cooled to room temperature after terminating
Discharging in distilled water, with after deionized water cyclic washing with recrystallized from acetonitrile, be placed in baking oven and be dried, obtain tying containing acid imide
The four cyano capping monomer of structure.Described 4-amino phthalonitrile is 2:1 with the mol ratio of anhydride monomers.
Step 2, the preparation of hyperbranched metal phthalocyanine oligomer containing imide structure
Four cyano capping monomer containing imide structure is dissolved in DMAC N,N' dimethyl acetamide (DMAc), dimethyl formyl
In amine (DMF), N-Methyl pyrrolidone (NMP) or quinoline, add transition metal salt, add (the NH of catalytic amount4)2MoO4,
It is heated to 150～160 DEG C of successive reactions 20～24h under nitrogen protection environment.Reaction is mixed after being cooled to room temperature after terminating by reaction
Compound pours the deionized water of pH < 1 into, washs with deionized water and acetonitrile backflow respectively, remove anti-after crude product is collected by filtration
Answer remaining inorganic salt and the unreacted four cyano capping monomer containing imide structure, be washed till the colourless rear cold ethanol of filtrate and rush
Wash, put in baking oven and be vacuum dried, obtain the hyperbranched metal phthalocyanine oligomer containing imide structure.Described containing acid imide
The four cyano capping monomer of structure and the mol ratio≤3:1 of metal ion in transition metal salt.
Described transition metal salt preferred transition metal hydrochlorate or acetate, further preferred Zn2+、Cu+Or Ni2+Hydrochloric acid
Salt or acetate.
In step one, described anhydride monomers is the one in formula (A)～formula (E).
In step one, the four cyano capping monomer containing imide structure prepared is in formula (a)～formula (b)
Kind.
Beneficial effects of the present invention:
No matter the hyperbranched metal phthalocyanine oligomer containing imide structure prepared in the present invention is at third-order nonlinearity light
Learning performance still to suffer from being obviously improved at heat stability, wherein, 5% thermal weight loss temperature is all more than 410 DEG C.
The hyperbranched metal phthalocyanine oligomer collection high performance structures containing imide structure prepared in the present invention and function
Macromolecule, in one, is expected to become the ideal material of optics.
Accompanying drawing explanation
In Fig. 1 embodiment 6～embodiment 10, the different structure nuclear-magnetism containing imide structure hyperbranched ZnPc oligomer is altogether
Shake spectrogram；Wherein, A curve is embodiment 6, and B curve is embodiment 7, and C curve is embodiment 8, and D curve is embodiment 9, E curve
For embodiment 10.
In Fig. 2 embodiment 6～embodiment 12, different structure contains the infrared of imide structure hyperbranched metal phthalocyanine oligomer
Spectrogram；Wherein, A curve is embodiment 6, and B curve is embodiment 7, and C curve is embodiment 8, and D curve is embodiment 9, and E curve is
Embodiment 10；F curve is embodiment 11, and G curve is embodiment 12.
The different structure ultraviolet containing imide structure hyperbranched metal phthalocyanine oligomer in Fig. 3 embodiment 6～embodiment 12
Absorb spectrogram；Wherein, A curve is embodiment 6, and B curve is embodiment 7, and C curve is embodiment 8, and D curve is embodiment 9, and E is bent
Line is embodiment 10；F curve is embodiment 11, and G curve is embodiment 12.
Fig. 4 embodiment 6 contains the thermogravimetric analysis figure of imide structure hyperbranched metal phthalocyanine oligomer.
Fig. 5～Figure 10 embodiment 6, embodiment 11 and embodiment 12 different structure hyperbranched metal phthalocyanine Han imide structure
The third-order nonlinear optical test phenogram of oligomer, in figure, vertical coordinate is normalized transmittance, and abscissa is that sample distance is burnt
The distance of point.
Detailed description of the invention
With the form of embodiment technical solution of the present invention it is further explained below and illustrates.
Embodiment 1～5 (preparation of the four cyano capping monomer containing imide structure)
4-amino phthalonitrile is dissolved in dry dimethyl sulfoxide (DMSO) solvent be placed in container, is passed through dry
In there-necked flask, respective acids anhydride monomer (A, B, C, D and E) is added, after quickly half an hour is reacted in stirring, to instead after dry nitrogen
Answering and add acetic anhydride and the mixed solution (volume ratio 5:4) of pyridine in system, rising temperature of reaction system is to 60 DEG C, and reaction 10 is little
Time.Reaction is cooled to room temperature discharging in distilled water after terminating, with after deionized water cyclic washing with recrystallized from acetonitrile, be placed in baking
Case is dried, obtains the four cyano capping monomer accordingly containing imide structure.Anhydride monomers kind and product are (containing imide structure
Four cyano capping monomer) corresponding relation as shown in table 1.
Table 1
Embodiment 6～12 (containing the preparation of imide structure hyperbranched ZnPc oligomer)
In three-necked bottle, three-necked bottle is sequentially installed with nitrogen port, glass stopper and drying tube.By 3mmol accordingly containing acyl
The four cyano capping monomer (a, b, c, d or e) of imine structure is dissolved in the N,N-dimethylacetamide (DMAc) of 40mL, adds
1mmol transition metal salt, adds catalyst, is heated to 160 DEG C of successive reactions 24h in a nitrogen environment.Reaction cools down after terminating
To room temperature, reactant mixture is poured into the deionized water of 600mL pH < 1.Deionization is used respectively after filtration of crude product being collected
Water and acetonitrile backflow washing, remove and react remaining transition metal salt and the four cyano capping monomer containing imide structure, be washed till
With cold alcohol flushing product after filtrate is colourless, puts in baking oven and be vacuum dried, obtain corresponding product.By in above example
The four cyano capping monomer containing imide structure, transition metal salt, the kind of catalyst and the addition that use prepare table 2, and
Gained productivity is listed in table 2.
Table 2
Embodiment 13
The present embodiment is with the difference of embodiment 6～12, and solvent for use is dimethylformamide (DMF), N-first
Base ketopyrrolidine (NMP) or quinoline.It is heated to 150～160 DEG C of successive reactions 20～24h under nitrogen protection environment.
Embodiment 14
The present embodiment is with the difference of embodiment 1～5, and reaction temperature, at 60～80 DEG C, is reacted 10～12 hours.
Product structure and the sign of performance
Fig. 1 is the different structure nuclear-magnetism containing imide structure hyperbranched ZnPc oligomer in the embodiment of the present invention 6～10
Resonance spectrogram, wherein embodiment 11 and embodiment 12 are because its center metal copper ion and nickel ion paramagnetism, and therefore nuclear-magnetism is altogether
The hydrogen that shakes spectrum, without response, therefore only lists in Fig. 1 in embodiment 6～embodiment 10 and prepares different structure containing imide structure over-expense
Change the nmr spectrum of ZnPc oligomer, Fig. 1 understands, near 11.5ppm, occur in that the new response belonging to carboxylic acid hydrogen
Peak-to-peak signal, provable product is carboxyl end seal.
As in figure 2 it is shown, 1610～1618cm-1Near have-C=N stretching vibration peak and 970cm-1Metal phthalocyanine C-N
Key absorption band；The 2700～3300cm of benzoic acid hydroxy-acid group-1Neighbouring wide absworption peak, 2230cm-1-CN peak near place is complete
Full disappearance；In oligomer infrared spectrum a series of belong to imide structure be positioned at 1778～1784cm-1,1374～
1384cm-1, 1080～1110cm-1, 721～740cm-1Infrared absorption peak demonstrate imide structure in course of reaction and be not subject to
To destroying, structure is the most complete.
As it is shown on figure 3, several oligomers exist stronger absworption peak, this absworption peak corresponds to phthalocyanine structure visible-range
The electron transition of interior Q band.
It is illustrated in figure 4 5% thermal weight loss temperature of embodiment 6 hyperbranched phthalocyanine oligomer, 7 kinds of hyperbranched phthalocyanine oligomers
5% thermal weight loss temperature all between 412～481 DEG C.
By the molecular weight of product, molecular weight distribution, uv absorption and the test result of thermogravimetric in embodiment 6～embodiment 12
As shown in table 3.
Table 3
The nonlinear optical property Z-of the hyperbranched metal phthalocyanine oligomer containing imide structure in above example sweeps
Method of retouching measures, and light source used is the q-multiplier Nd:YAG laser instrument of 21ps pulsewidth, 532nm wavelength, and single pulse energy is
0.51 μ J, repetition rate is 10Hz, and cuvette thickness is 2mm, with DMF (DMF) as solvent, polymeric material
Amount concentration is 5mg/mL.Such as Fig. 5～Figure 10, to show three rank carried out for embodiment 6, embodiment 11 and embodiment 12 non-
Linear optics test result figure, gained third-order nonlinear optical parameters is as shown in table 4.
Table 4
Claims (10)
1. the hyperbranched metal phthalocyanine oligomer containing imide structure, it is characterised in that this polymer molecular structure such as formula
(I) shown in,
In formula I, R represents Me represents transition metal ions, the equal molecule of number of this polymer
Amount Mn is 4000～20000g/mol.
A kind of hyperbranched metal phthalocyanine oligomer containing imide structure the most according to claim 1, it is characterised in that institute
Stating transition metal ions is Zn2+、Cu+Or Ni2+。
A kind of hyperbranched metal phthalocyanine oligomer containing imide structure the most according to claim 1, it is characterised in that should
Number-average molecular weight Mn of polymer is 4227～19505.
4., according to a kind of hyperbranched metal phthalocyanine oligomer containing imide structure described in claim 1,2 or 3, its feature exists
In, the molecular weight distribution of this polymer is 1.03～1.12.
5., according to a kind of hyperbranched metal phthalocyanine oligomer containing imide structure described in claim 1,2 or 3, its feature exists
In, 5% thermal weight loss temperature 412 of this polymer～481 DEG C.
6., according to a kind of hyperbranched metal phthalocyanine oligomer containing imide structure described in claim 1,2 or 3, its feature exists
In, the non-linear absorption coefficient α of this polymer2For (2.4～8.2) × 10-12m W-1, nonlinear viscoelastic piles n2For (3.9
～5.9) × 10-19m-2W, third-order nonlinear optical coefficient χ(3)For (3.2～5.2) × 10-13esu。
7. contain a preparation method for the hyperbranched metal phthalocyanine oligomer of imide structure as claimed in claim 1, specifically walk
It is rapid as follows,
Step one, the preparation of four cyano capping monomer containing imide structure
4-amino phthalonitrile is dissolved in dry dimethyl sulfoxide solvent be placed in container, after being passed through dry nitrogen
In there-necked flask, add anhydride monomers, quickly after stirring reaction 30～60min, in reaction system, add acetic anhydride and pyridine
Mixed solution, acetic anhydride and volume ratio 5:4 of pyridine, raise temperature of reaction system to 60～80 DEG C, react 10～12 hours；
Reaction is cooled to room temperature discharging in distilled water after terminating, with after deionized water cyclic washing with recrystallized from acetonitrile, be placed in baking oven
In be dried, obtain the four cyano capping monomer containing imide structure；Described 4-amino phthalonitrile and anhydride monomers mole
Ratio is 2:1；
Step 2, the preparation of hyperbranched metal phthalocyanine oligomer containing imide structure
Four cyano capping monomer containing imide structure is dissolved in DMAC N,N' dimethyl acetamide, dimethylformamide, N-methyl
In ketopyrrolidine or quinoline, add transition metal salt and add (the NH of catalytic amount4)2MoO4, under protective atmosphere, it is heated to 150
～160 DEG C of successive reactions 20～24h；React the deionized water that after being cooled to room temperature after terminating, reactant mixture is poured into pH < 1,
It is collected by filtration after crude product respectively with deionized water and acetonitrile backflow washing, removes and react remaining inorganic salt and unreacted
Four cyano capping monomer containing imide structure, be washed till filtrate colourless after use cold alcohol flushing, vacuum dried after, obtain containing acyl
The hyperbranched metal phthalocyanine oligomer of imine structure；In the described four cyano capping monomer containing imide structure and transition metal salt
Mol ratio≤the 3:1 of metal ion；
In step one, described anhydride monomers is the one in formula (A)～formula (E),
In step one, the four cyano capping monomer containing imide structure prepared is the one in formula (a)～formula (e),
The preparation method of the hyperbranched metal phthalocyanine oligomer containing imide structure the most according to claim 7, its feature
Being, described transition metal salt is hydrochlorate or the acetate of transition metal.
The preparation method of the hyperbranched metal phthalocyanine oligomer containing imide structure the most according to claim 8, its feature
It is, it is characterised in that described transition metal hydrochlorate or acetate are Zn2+、Cu+Or Ni2+Hydrochlorate or acetate.
10. according to the preparation method of the hyperbranched metal phthalocyanine oligomer containing imide structure described in claim 7,8 or 9,
It is characterized in that, under protective atmosphere, heating-up temperature is 160 DEG C, and the response time is 24 hours.
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| CN111072961A (en) * | 2019-12-18 | 2020-04-28 | 武汉华星光电半导体显示技术有限公司 | Film material and method for producing film material |
| WO2021120348A1 (en) * | 2019-12-18 | 2021-06-24 | 武汉华星光电半导体显示技术有限公司 | Thin film material and preparation method for thin film material |
| CN112111132A (en) * | 2020-09-24 | 2020-12-22 | 中国科学院长春光学精密机械与物理研究所 | Conjugated microporous poly phthalocyanine-graphene composite laser protection material and preparation method thereof |
| CN112111132B (en) * | 2020-09-24 | 2021-10-08 | 中国科学院长春光学精密机械与物理研究所 | Conjugated microporous poly phthalocyanine-graphene composite laser protection material and preparation method thereof |
| CN112159519B (en) * | 2020-09-24 | 2021-07-06 | 中国科学院长春光学精密机械与物理研究所 | Porous poly-phthalocyanine laser protection material with carbon bridging and preparation method thereof |
| CN112159519A (en) * | 2020-09-24 | 2021-01-01 | 中国科学院长春光学精密机械与物理研究所 | Porous poly-phthalocyanine laser protection material with carbon bridging and preparation method thereof |
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