CN103554489B - Azobenzene polymer, preparation method and application thereof - Google Patents
Azobenzene polymer, preparation method and application thereof Download PDFInfo
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- CN103554489B CN103554489B CN201310491388.5A CN201310491388A CN103554489B CN 103554489 B CN103554489 B CN 103554489B CN 201310491388 A CN201310491388 A CN 201310491388A CN 103554489 B CN103554489 B CN 103554489B
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- 229920000642 polymer Polymers 0.000 title claims abstract description 36
- DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical compound C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 title abstract description 13
- 238000002360 preparation method Methods 0.000 title abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims abstract description 21
- 239000004065 semiconductor Substances 0.000 claims abstract description 19
- 238000000034 method Methods 0.000 claims abstract description 9
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 claims description 21
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 claims description 16
- 238000006116 polymerization reaction Methods 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 8
- 150000001875 compounds Chemical class 0.000 abstract description 7
- 230000015572 biosynthetic process Effects 0.000 abstract description 6
- 238000003786 synthesis reaction Methods 0.000 abstract description 6
- 239000011358 absorbing material Substances 0.000 abstract description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 abstract 1
- 229910017912 NH2OH Inorganic materials 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 230000031700 light absorption Effects 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000000178 monomer Substances 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical class [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- 239000012954 diazonium Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 5
- 229920001197 polyacetylene Polymers 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- 229920002098 polyfluorene Polymers 0.000 description 4
- 229920006389 polyphenyl polymer Polymers 0.000 description 4
- 229920000123 polythiophene Polymers 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- VJYJJHQEVLEOFL-UHFFFAOYSA-N thieno[3,2-b]thiophene Chemical compound S1C=CC2=C1C=CS2 VJYJJHQEVLEOFL-UHFFFAOYSA-N 0.000 description 4
- 239000004734 Polyphenylene sulfide Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 229920000767 polyaniline Polymers 0.000 description 3
- 229920000069 polyphenylene sulfide Polymers 0.000 description 3
- 229920000128 polypyrrole Polymers 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- 238000001291 vacuum drying Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 2
- 238000006149 azo coupling reaction Methods 0.000 description 2
- 239000004020 conductor Substances 0.000 description 2
- 229920000547 conjugated polymer Polymers 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- FHIVAFMUCKRCQO-UHFFFAOYSA-N diazinon Chemical compound CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FHIVAFMUCKRCQO-UHFFFAOYSA-N 0.000 description 2
- 150000001989 diazonium salts Chemical class 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 230000005693 optoelectronics Effects 0.000 description 2
- 230000000630 rising effect Effects 0.000 description 2
- 238000005185 salting out Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- GYVYGTTZKLHDON-UHFFFAOYSA-N 2-anilinophenol Chemical group OC1=CC=CC=C1NC1=CC=CC=C1 GYVYGTTZKLHDON-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229920003180 amino resin Polymers 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 210000003746 feather Anatomy 0.000 description 1
- 244000144992 flock Species 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- DQLGIONSPPKALA-UHFFFAOYSA-N phenylazanium;phenoxide Chemical group NC1=CC=CC=C1.OC1=CC=CC=C1 DQLGIONSPPKALA-UHFFFAOYSA-N 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Landscapes
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Abstract
The invention relates to an azobenzene polymer, a preparation method and application thereof, relates to a novel polymer semiconductor material with a main chain of aromatic ring and azo conjugate and a preparation method thereof, belongs to the field of new materials and chemical synthesis, and comprises a compound of a general formula (I), wherein x can be NH2OH, OR, etc. The invention also provides a method for further modifying the polymer semiconductor material. The polymer semiconductor material has the advantages of good light absorption and simple synthesis process, and can be used as photoelectric conversion, conductive and wave-absorbing materials and the like.
Description
Technical field
The present invention relates to azobenzene polymer, preparation method and the usage, the compound is that a kind of main chain is azobenzene
Conjugated polymer, be a kind of new polymers semi-conducting material, available for opto-electronic conversion, the purposes such as conductive and absorbing material.
Background technology
Polymer is polymerized the material that the macromolecular with chain structure formed by monomer, and polymer semiconductor refers to
Polymer with semiconductor property, electrical conductivity is in 10-8~103(Ω·cm-1) in the range of.Polymer semiconductor develops very
Rapidly, and have started to step into the practical stage.But due to its less stable, application is also by a definite limitation at present.Polymer half
The energy gap of conductor is suitable with the energy gap of inorganic semiconductor, for example, the energy gap of Trans-polyacetylene is 1.5eV.Mix
Miscellaneous and illumination can make the electrical conductivity of polymer semiconductor improve several magnitudes.Polymer semiconductor can be used to make light-emitting diodes
The devices such as pipe, FET, its preparation technology is simple, it is cheap, easily tied into big face, and be easy to MOLECULE DESIGN, thus more next
More it is taken seriously.
Earliest polymer semiconductor is the Trans-polyacetylene that Hideki Shirakawa in 1974 is found, the polymer of new construction is not by
It is disconnected to find.Current polymer semiconductor's type have polyacetylene, polyaniline, it is poly- to styrene support, polyfluorene, polythiophene, polypyrrole,
The complex of polyphenylene sulfide, polyphenyl 1,4-Dithiapentalene and various conjugated structures, each type of polymer have many derivatives again.
Its structure is as follows：
Polyacetylene
It is poly- that styrene is supportted
Polyaniline
Polyphenylene sulfide
Polypyrrole
Polythiophene
Polyfluorene
Polyphenyl 1,4-Dithiapentalene
There is outstanding photoelectric conversion capacity to obtain more research, the above for polythiophene, polyfluorene and polyphenyl 1,4-Dithiapentalene at present
Various conjugate units can be designed that the new polymers semi-conducting material of different band gap widths by various combination.
The synthetic route of several compound semi-conducting materials of birdsing of the same feather flock together can be divided into three classes above：The first kind, Trans-polyacetylene is in gas phase
Catalytic polymerization film forming；The oxidation polymerization or using electropolymerization in acid condition of second class, polyaniline and polyphenylene sulfide；3rd
Class, the poly- complex to styrene support, polyfluorene, polythiophene, polypyrrole, polyphenyl 1,4-Dithiapentalene and various conjugated structures use
Grignard reagents and then the technique being coupled synthesis is made in monomer, and the synthesis side reaction of this route is more, control is difficult, cost is high, typically
Synthesis is reacted on a small scale in laboratory.
The content of the invention
The present invention proposes that a kind of its polymer architecture of the conjugated polymer semi-conducting material of new backbone structure is as follows：
Poly- azobenzene
Wherein x can be NH2, the group such as OH, OR
Diazo-coupling reactions are used in the synthesis of main polymer chain by the present invention.The present invention is achieved in that according to x bases
The difference of group presses two kinds of reaction schemes.
The first kind：X is NH2.O-phenylenediamine and nitrite generate diazol under low temperature, strong acidic condition, then soon
Speed heating room temperature, reacts 24 hours.Through experiment, the NH of contraposition and meta2Also can carry out this reaction, but its product be it is powdered,
It is difficult to apply film forming, and application is poor.See reaction scheme 1.
Second class：X is OH or OR.O-aminophenol generates diazol under low temperature, strong acidic condition, then fast velocity modulation
PH is saved to strong basicity, room temperature is warming up to, reacts 24 hours.Through experiment, the OH (OR) of contraposition and meta can also carry out this reaction, but
Its product is powdered, and it is difficult to apply film forming, and application is poor.See reaction scheme 2.
Reaction scheme 1：
Reaction scheme 2：
Because diazo-coupling reactions diazonium key NH on phenyl ring2Or OH (OR) contraposition or ortho position coupling（Because of steric hindrance reason,
Preferential contraposition）, therefore NH2Or OH (OR) is different from the position relationship of diazonium key（Ortho position, contraposition and meta）And cause polymer
Form it is different.Diazonium key and the NH on phenyl ring2Or OH (OR) be in meta and contraposition when, because diazonium key key be coupled key deposit
In certain angle, cause to distort glomeration automatically during polymerization, product is macroscopically being shown as to be powdered, only on phenyl ring
NH2Or OH (OR) and diazonium key are in ortho position and can just aggregate into chain structure.It the experiment proved that contraposition and metacompaund are powder,
Ortho-product has the high molecular characteristic of chain, has good film forming, can preferably be applied to opto-electronic conversion, conductive and suction
Wave material.
It is dark reddish brown sticky oil thing under compound poly-o-phenylenediamine normal temperature.In the infrared spectrum of monomer o-phenylenediamine
3384cm-1And 3287cm-1For N-H stretching vibration peak, 1633cm-1For N-H deformation vibration, 1273cm-1For Ph-N-
H2Middle C-N stretching vibration peaks, these absworption peaks no longer occur in azobenzene polymer, occur in azobenzene polymer new
Absworption peak 1287cm-1, the stretching vibration peak for being C-N in Ph-N=N, illustrate that monomer has azobenzene when being polymerize
Unit generates, and at 752cm-1 knowable to the presence of absworption peak, the substitution on phenyl ring is contraposition substitution, illustrates that monomer polymerization is logical
Cross what linear coupling was carried out.Compound poly-o-phenylenediamine hydrogen nuclear magnetic resonance modal data is：1H NMR(400MHz,DMSO)δ8.51
(s,0H),7.67(t,J=9.4Hz,1H),7.56(t,J=8.5Hz,1H),7.20–7.06(m,2H),7.05–6.97(m,1H),
6.97–6.87(m,1H),6.87–6.71(m,2H),6.62(dd,J=18.0,7.2Hz,1H),6.47(t,J=7.3Hz,1H)。
It is 17110 dalton with GPC detections Mn, Mw is 38383 dalton, and its polydispersity is 2.243354, is reflected in polymerization
Form the complexity of polymer molecule.
The poly- o-aminophenol of compound is dark thick paste.3376cm in the infrared spectrum of monomer o-aminophenol-1
And 3305cm-1For the stretching vibration peak for the N-H being connected with phenyl ring, 1601cm-1 is N-H deformation vibration, and 1265cm-1 is
C-N stretching vibration peaks in Ph-N-H2.These absworption peaks no longer occur in azobenzene polymer, in azobenzene polymer
There is new absworption peak 1338cm-1, be the stretching vibration peak of C-N in Ph-N=N, illustrate monomer when being polymerize
There is azo-benzene units generation, at 745cm-1 knowable to the presence of absworption peak, the substitution on phenyl ring is contraposition substitution, illustrates monomer
Polymerization is by being linearly coupled progress.The poly- o-aminophenol hydrogen nuclear magnetic resonance modal data of compound is：1H NMR(400MHz,
DMSO)δ7.93(d,J=3.1Hz,1H),7.91(d,J=3.1Hz,1H),7.46(d,J=3.0Hz,1H),7.44(d,J=
3.0Hz,1H).It is 28928 dalton with GPC detections Mn, Mw is 78141 dalton, and its polydispersity is 2.7012, is reflected
The complexity of polymer molecule is formed in polymerization.
In the electrical conductivity of RTS-8 four-point probes test two kinds of polymer, the surface conductivity of pure o-phenylenediamine is
6.87×10-5S·cm-1, the surface conductivity of pure o-aminophenol is 8.17 × 10-5S·cm-1.Its conductance, which reaches, partly to be led
The conductive extensions of body, it was demonstrated that it belongs to polymer semiconductor.
In view of aforementioned two kinds of azobenzene polymer molecular weight are not high, about 20000 dalton to 50000 dalton.
Its form has shape thing and paste to be sticky.To improve its mechanical property, polycondensation reaction can be carried out with aldehydes, form similar phenol
The formation molecular weight of urea formaldehyde and amino resins is bigger, the more complicated polymer of structure.
Brief description of the drawings
Accompanying drawing 1：The infrared spectrum collection of illustrative plates of poly-o-phenylenediamine and o-phenylenediamine, wherein upper figure is o-phenylenediamine, figure below is poly-
O-phenylenediamine
Accompanying drawing 2：The H of poly-o-phenylenediamine1- NMR spectra
Accompanying drawing 3：Gather the infrared spectrum collection of illustrative plates of adjacent phenylamino phenol and o-aminophenol, wherein upper figure is o-aminophenol,
Figure below is poly- o-aminophenol
Accompanying drawing 4：The H of poly- o-aminophenol1- NMR spectra
Embodiment
One of embodiment：
The accurate isothermal reaction kettle for weighing 54g (0.5mol) o-phenylenediamine and adding 0 DEG C, reactor volume 2L, glass material.
Measure the concentrated hydrochloric acid 105ml that mass fraction is 37%（About 1.25mol）, it is slowly added to isothermal reactor kettle.All adjacent benzene are treated in stirring
Two amine solvents.34.5g (0.5mol) natrium nitrosum accurately is weighed, is dissolved with 50mL frozen water.Sodium nitrite in aqueous solution is being stirred
In the case of be slowly added in reactor, control adding speed, avoid producing very much nitrous acid soon, avoid reaction temperature from rising too fast.
After complete sodium nitrite in aqueous solution to be added, the temperature of reactor is raised to 25 DEG C, is reacted 24 hours, allows the diazonium compound of generation
Fully reaction, continues to polymerize.Reaction system will be divided into two layers, and upper strata is the aqueous solution, and lower floor is dark reddish brown sticky oil thing.With
Sand core funnel is filtered by vacuum, and obtains this dark reddish brown sticky oil thing.This dark reddish brown sticky oil thing is dissolved with ethanol, mistake
The salt separated out is filtered, ethanol is removed in vacuum drying oven.Twice of this salting-out process is repeated, produces pure poly-o-phenylenediamine.Yield
About 70~80%.
The two of embodiment：
The accurate isothermal reaction kettle for weighing 54g (about 0.5mol) o-aminophenol and adding 0 DEG C, reactor volume 2L, glass
Material.Measure the concentrated hydrochloric acid 105ml that mass fraction is 37%（About 1.25mol）, it is slowly added to isothermal reactor kettle.Institute is treated in stirring
There is o-phenylenediamine dissolving.34.5g (0.5mol) natrium nitrosum accurately is weighed, is dissolved with 50mL frozen water.By sodium nitrite in aqueous solution
It is slowly added under agitation in reactor, controls adding speed, avoid producing very much nitrous acid soon, avoid reaction temperature from rising
It is too fast.Solution above, is slowly added in this sodium hydroxide solution by the another sodium hydroxide solution 0.5L for preparing 10mol/L,
It is to be added complete, the temperature of reactor is raised to 25 DEG C, is reacted 24 hours, is allowed the diazonium compound of generation fully to react, continue to gather
Close.Obtained solution is dried in vacuum drying oven and obtains dark thick paste.This dark thick paste ethanol is molten
Solution, the salt of precipitation is filtered, ethanol is removed in vacuum drying oven.Twice of this salting-out process is repeated, produces pure poly- adjacent aminobenzene
Phenol.Yield about 70~80%.
Claims (5)
1. polymer semiconducting material, it has the structure of logical formula (I), and wherein x is NH2Or OH groups
2. preparing the method for the polymer semiconducting material described in claim 1, it is NH to lead to x in formula (I)2When, including following multistep
Course of reaction：
3. the method for the polymer semiconducting material described in claim 1 is prepared, when x is OH in logical formula (I), including following multistep
Course of reaction：
4. method as claimed in claim 2, wherein NO2 -Mol ratio with o-phenylenediamine is 1：1, hydrochloric acid and o-phenylenediamine rub
You are than being 2.5：1, diazotising temperature is 0 DEG C -4 DEG C, and polymerization temperature is 25 DEG C.
5. method as claimed in claim 3, wherein NO2 -Mol ratio with o-aminophenol is 1：1, hydrochloric acid and o-phenylenediamine
Mol ratio is 2.5：1, diazotising temperature is 0 DEG C -4 DEG C, and polymerization temperature is 25 DEG C.
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| CN103936982B (en) * | 2014-04-21 | 2016-01-27 | 苏州大学张家港工业技术研究院 | A kind of backbone chain type azobenzene polymer and preparation method thereof |
| CN104319350B (en) * | 2014-11-07 | 2016-11-09 | 河北联合大学 | One class is for the azapyrimidines class double charge organic hole transport material of all solid state quantum dot sensitized solaode |
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| US4069012A (en) * | 1974-03-26 | 1978-01-17 | Cassella Farbwerke Mainkur Aktiengesellschaft | Dyeing of polyester fabric with disazo dye |
| JPS60130621A (en) * | 1983-12-19 | 1985-07-12 | Showa Denko Kk | Production of polyazophenylene |
| JPS6197328A (en) * | 1984-10-17 | 1986-05-15 | Kao Corp | Polyazophenylene film and display element |
| DE10325808A1 (en) * | 2003-06-06 | 2004-12-23 | Basf Ag | Anionic azo dyes and their metal complexes for leather dyeing |
| CN101134811A (en) * | 2006-07-25 | 2008-03-05 | 株式会社艾迪科 | Polymeric azo compound |
| CN102617855B (en) * | 2012-04-13 | 2013-10-09 | 苏州大学 | Cyclic polymer and preparation method thereof |
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