CN109535032A - Derivative and its preparation method and application is supportted to styrene containing naphthalene ring and the poly- of cyano - Google Patents
Derivative and its preparation method and application is supportted to styrene containing naphthalene ring and the poly- of cyano Download PDFInfo
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- CN109535032A CN109535032A CN201811602627.9A CN201811602627A CN109535032A CN 109535032 A CN109535032 A CN 109535032A CN 201811602627 A CN201811602627 A CN 201811602627A CN 109535032 A CN109535032 A CN 109535032A
- Authority
- CN
- China
- Prior art keywords
- cyano
- poly
- naphthalene ring
- derivative
- styrene
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- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 title claims abstract description 338
- 125000004093 cyano group Chemical group *C#N 0.000 title claims abstract description 149
- 125000001624 naphthyl group Chemical group 0.000 title claims abstract description 146
- 238000002360 preparation method Methods 0.000 title claims abstract description 22
- 239000000463 material Substances 0.000 claims abstract description 46
- 238000001514 detection method Methods 0.000 claims abstract description 22
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 claims abstract description 19
- 239000000178 monomer Substances 0.000 claims abstract description 18
- 239000002360 explosive Substances 0.000 claims abstract description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 88
- -1 dicyano naphthalene nucleus diamine Chemical class 0.000 claims description 71
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 50
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 claims description 44
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 37
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 30
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 24
- 239000003960 organic solvent Substances 0.000 claims description 23
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 21
- 239000007789 gas Substances 0.000 claims description 21
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 20
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 claims description 20
- 239000002904 solvent Substances 0.000 claims description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
- 229920000642 polymer Polymers 0.000 claims description 16
- 238000003756 stirring Methods 0.000 claims description 16
- 239000007787 solid Substances 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 230000002378 acidificating effect Effects 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 13
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 12
- 239000007788 liquid Substances 0.000 claims description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 11
- 239000000741 silica gel Substances 0.000 claims description 11
- 229910002027 silica gel Inorganic materials 0.000 claims description 11
- 239000003054 catalyst Substances 0.000 claims description 10
- 238000001816 cooling Methods 0.000 claims description 10
- SIPUZPBQZHNSDW-UHFFFAOYSA-N diisobutylaluminium hydride Substances CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 claims description 10
- CMQCNTNASCDNGR-UHFFFAOYSA-N toluene;hydrate Chemical compound O.CC1=CC=CC=C1 CMQCNTNASCDNGR-UHFFFAOYSA-N 0.000 claims description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 229940113088 dimethylacetamide Drugs 0.000 claims description 6
- 239000011521 glass Substances 0.000 claims description 6
- 239000003638 chemical reducing agent Substances 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 5
- 238000003760 magnetic stirring Methods 0.000 claims description 5
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 5
- 238000010992 reflux Methods 0.000 claims description 5
- 239000006228 supernatant Substances 0.000 claims description 5
- 238000010792 warming Methods 0.000 claims description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
- 239000012491 analyte Substances 0.000 claims description 3
- LNDJVIYUJOJFSO-UHFFFAOYSA-N cyanoacetylene Chemical group C#CC#N LNDJVIYUJOJFSO-UHFFFAOYSA-N 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- 239000011591 potassium Substances 0.000 claims description 3
- 230000005622 photoelectricity Effects 0.000 claims description 2
- ZWKNLRXFUTWSOY-QPJJXVBHSA-N (e)-3-phenylprop-2-enenitrile Chemical compound N#C\C=C\C1=CC=CC=C1 ZWKNLRXFUTWSOY-QPJJXVBHSA-N 0.000 claims 1
- ZRBROGSAUIUIJE-UHFFFAOYSA-N azanium;azane;chloride Chemical compound N.[NH4+].[Cl-] ZRBROGSAUIUIJE-UHFFFAOYSA-N 0.000 claims 1
- MJYNUKMKBLYKKQ-UHFFFAOYSA-N dichloromethane;styrene Chemical compound ClCCl.C=CC1=CC=CC=C1 MJYNUKMKBLYKKQ-UHFFFAOYSA-N 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- 230000020477 pH reduction Effects 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 229920002554 vinyl polymer Polymers 0.000 description 28
- 239000010408 film Substances 0.000 description 20
- UHSCCYVVMZXUGS-UHFFFAOYSA-N 1-N,2-N-dinaphthalen-1-yl-1-N,2-N-diphenylbenzene-1,2-diamine Chemical compound C1(=CC=CC2=CC=CC=C12)N(C1=CC=CC=C1)C1=C(C=CC=C1)N(C1=CC=CC2=CC=CC=C12)C1=CC=CC=C1 UHSCCYVVMZXUGS-UHFFFAOYSA-N 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 12
- 239000002585 base Substances 0.000 description 10
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzenecarboxaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 9
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 8
- 230000004580 weight loss Effects 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- 230000002441 reversible effect Effects 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 150000002790 naphthalenes Chemical class 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- 241001597008 Nomeidae Species 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 235000019270 ammonium chloride Nutrition 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 125000003367 polycyclic group Polymers 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 238000002845 discoloration Methods 0.000 description 3
- 238000013467 fragmentation Methods 0.000 description 3
- 238000006062 fragmentation reaction Methods 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229920006254 polymer film Polymers 0.000 description 3
- 150000005839 radical cations Chemical class 0.000 description 3
- 230000035945 sensitivity Effects 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- VWZKHKRVSXWHAC-UHFFFAOYSA-N 3-($l^{1}-oxidanylmethyl)heptane Chemical compound CCCCC(CC)C[O] VWZKHKRVSXWHAC-UHFFFAOYSA-N 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- YKYMGFHOJJOSEB-UHFFFAOYSA-N butan-1-ol;potassium Chemical compound [K].CCCCO YKYMGFHOJJOSEB-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000003471 mutagenic agent Substances 0.000 description 2
- 231100000707 mutagenic chemical Toxicity 0.000 description 2
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- MBPCKEZNJVJYTC-UHFFFAOYSA-N 4-[4-(n-phenylanilino)phenyl]aniline Chemical compound C1=CC(N)=CC=C1C1=CC=C(N(C=2C=CC=CC=2)C=2C=CC=CC=2)C=C1 MBPCKEZNJVJYTC-UHFFFAOYSA-N 0.000 description 1
- 241001391944 Commicarpus scandens Species 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 235000019658 bitter taste Nutrition 0.000 description 1
- 150000007516 brønsted-lowry acids Chemical class 0.000 description 1
- 150000007528 brønsted-lowry bases Chemical class 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000002484 cyclic voltammetry Methods 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000012769 display material Substances 0.000 description 1
- 208000021760 high fever Diseases 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- XQZYPMVTSDWCCE-UHFFFAOYSA-N phthalonitrile Chemical class N#CC1=CC=CC=C1C#N XQZYPMVTSDWCCE-UHFFFAOYSA-N 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/42—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being further bound to other hetero atoms
- C07C255/43—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being further bound to other hetero atoms the carbon skeleton being further substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
- G01N21/643—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" non-biological material
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/14—Macromolecular compounds
- C09K2211/1408—Carbocyclic compounds
- C09K2211/1433—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Physics & Mathematics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Immunology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Optics & Photonics (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Pathology (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Luminescent Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Derivative and its preparation method and application is supportted to styrene containing naphthalene ring and the poly- of cyano, the present invention relates to support derivative and its preparation method and application to styrene containing naphthalene ring and the poly- of cyano.Derivative and its preparation method and application is supportted to styrene containing naphthalene ring and the poly- of cyano the present invention provides a kind of.The present invention synthesizes the dialdehyde monomer containing naphthalene ring, then prepares and supports derivative to styrene containing naphthalene ring and the poly- of cyano, which is applied to electrochromic material, hole mobile material, camouflage material, automobile rearview mirror material as photoelectric material；It can also be used in organic acid, explosive detection.Present invention application Photoelectric Detection and display field.
Description
Technical field
The present invention relates to support derivative and its preparation method and application to styrene containing naphthalene ring and the poly- of cyano.
Background technique
Poly- is the outstanding high temperature polymeric materials of a kind of comprehensive performance to styrene support (PPV), has good chemistry
Stability, excellent dielectric properties and radiation resistance etc. can be prepared into film, composite material, insulated paint, capacitor equipment
Material, is widely used in the fields such as aerospace, electroluminescent, sensor.Although poly- support excellent combination property to styrene, pass
Uniting, there are some disadvantages by PPV, and such as the problems such as difficulty of processing is high, dissolubility is poor, film strength is poor, flexible difference is easy to break, this is big
The poly- application to styrene timbering material industrially is limited greatly.Therefore, we introduce alkyloxy side chain on PPV to enhance it
Dissolubility, while electrophilic group cyano is introduced on PPV main chain to improve its Electronic Performance, reduce its energy band.In addition, now more
It is required that material has multi-functional and miniaturization, and can be integrated in a small chip, and traditional PPV is as photoelectric material
With detection display material since the limitation of its dissolubility and processing performance is slightly inadequate.Therefore, PPV class material Photoelectric Detection with
The application of display field is all to be improved always.
Summary of the invention
The present invention is to solve the problems, such as that existing PPV class material using less, is provided in Photoelectric Detection and display field
It is poly- to styrene support derivative and its preparation method and application containing naphthalene ring and cyano.
The present invention is poly- to benzene containing naphthalene ring and cyano to styrene support derivative containing the poly- of naphthalene ring and cyano
Vinylene derivative P1 supports derivative P2 to styrene containing naphthalene ring and the poly- of cyano；
The poly- structural formula for supportting derivative P1 to styrene wherein containing naphthalene ring and cyano is as follows:
,
The integer that n is 3~10 in formula；
It is wherein poly- as follows to styrene support derivative P2 structural formula containing naphthalene ring and cyano:
,
The integer that n is 3~10 in formula.
The present invention containing naphthalene ring and cyano it is poly- to styrene support derivative the preparation method comprises the following steps:
One, the monomer of the dialdehyde containing naphthalene ring is synthesized
By dicyano naphthalene nucleus diamine with except water-toluene mixes, logical nitrogen is vacuumized, then be placed in low-temp reaction kettle, cooled down
To -70 degrees Celsius, reducing agent diisobutyl aluminium hydride is added, 10min is stirred under -70 degrees celsius, closes cooling valve, keeps
Until temperature of reaction system time is warmed to room temperature, taking-up reaction system, which is placed in, to be continued to stir on magnetic stirring apparatus, then is successively added for stirring
Enter the ammonia spirit of acetone, ethyl acetate, ammonium chloride, obvious layering occurs in stirring to system, and upper layer is supernatant liquid, lower layer
There is solid precipitation, system is filtered, gained liquid revolving obtains dialdehyde monomer；
Two, it prepares and derivative is supportted to styrene containing naphthalene ring and the poly- of cyano
By dialdehyde monomer, solvent, 2- (2- ethyl hexyl oxy) -5- methoxyl group -1,4- benzene diacetonitrile containing cyano, tertiary fourth
Potassium alcoholate and catalyst tetrabutylammonium hydroxide are added in there-necked flask, are warming up to 50 DEG C and are stirred at reflux 20min or so, pour into after cooling
With in the methanol of acetic acid, refiltering and washing solid with methanol until methanol is without color, obtained solid is dried in vacuo,
It obtains supportting derivative to styrene containing naphthalene ring and the poly- of cyano；
Wherein the dicyano naphthalene nucleus diamine in step 1, diisobutyl aluminium hydride mass volume ratio be (1.0-1.5) g:
(2-3)mL；
Remove water-toluene and the volume mass ratio of dicyano naphthalene nucleus diamine in step 1 are 10mL:(1.0-1.5g)；
The mass volume ratio of acetone and dicyano naphthalene nucleus diamine in step 1 are as follows: (2-3) mL:(1.0-1.5g)；
The volume mass ratio of ethyl acetate and dicyano naphthalene nucleus diamine in step 1 are as follows: (2-3) m；:(1.0-1.5g)；
2- (2- ethyl hexyl oxy) -5- methoxyl group -1,4- benzene diacetonitrile of dialdehyde monomer, cyano-containing in step 2, uncle
Butanol potassium and the mass volume ratio of catalyst tetrabutylammonium hydroxide are 0.2g:0.15g:0.12g:5mL；
The volume mass ratio of solvent and dialdehyde monomer in step 2 is 20mL 0.2g；Solvent is the tert-butyl alcohol and tetrahydro furan
The 1:1 by volume that mutters is mixed；
Dicyano naphthalene nucleus diamine is N, N '-two (4- benzene first cyanogen)-N, N '-diphenyl-phenylenediamine or N, N '-two (4- benzene first
Cyanogen)-N, N '-diphenyl-benzidine.
Poly- application to styrene support derivative as photoelectric material of the present invention containing naphthalene ring and cyano.
The present invention answers styrene support derivative as acidic and alkaline gas detection material containing naphthalene ring and the poly- of cyano
With.
The present invention applies in explosive detection styrene support derivative containing naphthalene ring and the poly- of cyano.
Beneficial effects of the present invention:
The present invention greatly expands the application range of PPV class material, and poly- support to styrene with cyano containing Long carbon chain is gathered
Object material is closed, since its excellent heat resistance and mechanical performance cause the great interest of researcher.There to be destruction
The naphthalene nucleus and Long carbon chain of bulk property are introduced into poly- in styrene support structure, being not only able to maintain original poly- high fever supportted to styrene
Stability, and being capable of increasing its solubility enhances film forming ability, and this is not only advantageous to the thin-film electro mutagens of manufacture large area
Color device additionally provides electric activity center to promote the processing and application of electrochromic device；It is prepared by the present invention poly- to benzene second
Alkene supports derivative using plane formula dialdehyde as monomer, and the strong effect power between polymer molecular chain can be effectively reduced, and increases
The dissolubility of polymer, while it being easily formed radical cation, show the color different from middle condition.Containing in the present invention
Naphthalene ring and the poly- of cyano have very high performance resistant to high temperature to styrene support derivative, generally under the atmosphere of nitrogen, point
Temperature is solved at 350 DEG C or more, is suitble to use in the devices.The present invention is derived containing poly- support to styrene of naphthalene ring and cyano
Film is made in object material, does not have embrittlement and Fragmentation Phenomena on ITO substrate, and good wet ability is shown on ITO substrate.This
Mean to prepare and there is good film Formation and characteristics, Ke Yiyong to styrene support derivant material containing naphthalene ring and the poly- of cyano
To make the film of large area.Thin polymer film is able to maintain circulating ring and has good stability during applying voltage, can follow
It ring 20 times or more and has good stability.
The poly- electrochromic property to styrene support derivative of the invention has following superiority in practical applications:
(1) there is good electrochemical redox invertibity, be still able to maintain after tens redox cycles reversible；(2)
The response time of color change is fast, after making alive, can change colour rapidly within 0.8 second；(3) variation of color is reversible
's；(4) color change high sensitivity；(5) there is higher cycle life；(6) there is preferable chemical stability in material discoloration front and back,
Under normal temperature and pressure, it may be stabilized in air.(7) derivative P1 is supportted to soda acid to styrene containing naphthalene ring and the poly- of cyano
Property gas and picric acid have response；Poly- containing naphthalene ring and cyano is to styrene support derivative P2 to acidic and alkaline gas and quick-fried
Fried object TNT, picric acid have response.
Detailed description of the invention
Fig. 1 is the poly- INFRARED SPECTRUM that derivative is supportted to styrene containing naphthalene ring and cyano prepared by embodiment one and two
Figure；
Fig. 2 is the poly- proton magnetic spectrum that derivative P1 is supportted to styrene containing naphthalene ring and cyano prepared by embodiment one
Figure；
Fig. 3 is the poly- proton magnetic spectrum that derivative P2 is supportted to styrene containing naphthalene ring and cyano prepared by embodiment two
Figure；
Fig. 4 is the poly- cyclic voltammetric that derivative P1 is supportted to styrene containing naphthalene ring and cyano prepared by embodiment one
Figure；
Fig. 5 is the poly- cyclic voltammetric that derivative P2 is supportted to styrene containing naphthalene ring and cyano prepared by embodiment two
Figure；
Fig. 6 is the poly- electrochromism that derivative P1 is supportted to styrene containing naphthalene ring and cyano prepared by embodiment one
Figure；
Fig. 7 is the poly- electrochromism that derivative P2 is supportted to styrene containing naphthalene ring and cyano prepared by embodiment two
Figure；
Fig. 8 is the poly- electroluminescent fluorescent that derivative P1 is supportted to styrene containing naphthalene ring and cyano prepared by embodiment one
Figure；
Fig. 9 is the poly- electroluminescent fluorescent that derivative P2 is supportted to styrene containing naphthalene ring and cyano prepared by embodiment two
Figure；
Figure 10 is the poly- thermal weight loss that derivative is supportted to styrene containing naphthalene ring and cyano prepared by embodiment one and two
Curve graph；
Figure 11 supports derivative to acid-base property to styrene containing naphthalene ring and the poly- of cyano for prepared by embodiment one and two
The response diagram of gas；
Figure 12 supports derivative P1 to organic bitter to styrene containing naphthalene ring and the poly- of cyano for prepared by embodiment one
Sour detection figure；
Figure 13 supports derivative P2 to organic bitter to styrene containing naphthalene ring and the poly- of cyano for prepared by embodiment two
Sour detection figure；
Figure 14 supports derivative P2 to explosive TNT to styrene containing naphthalene ring and the poly- of cyano for prepared by embodiment two
Detection figure.
Specific embodiment
Technical solution of the present invention is not limited to the specific embodiment of act set forth below, further include each specific embodiment it
Between any combination.
Specific embodiment 1: present embodiment is containing naphthalene nucleus to styrene support derivative containing naphthalene ring and the poly- of cyano
Structure and the poly- of cyano support derivative P1 to styrene or support derivative P2 to styrene containing naphthalene ring and the poly- of cyano；
The poly- structural formula for supportting derivative P1 to styrene wherein containing naphthalene ring and cyano is as follows:
,
The integer that n is 3~10 in formula；
It is wherein poly- as follows to styrene support derivative P2 structural formula containing naphthalene ring and cyano:
,
The integer that n is 3~10 in formula.
Present embodiment containing naphthalene ring and cyano it is poly- to styrene support derivative P1 be poly- 1- (N, N '-diphenyl-N,
N '-dinaphthyl-phenylenediamine) -2- cyano -2- (2- methoxyl group -4- (1- vinyl) -5- (2- ethyl hexyl oxy)) phenyl second
Alkene；It is poly- 1- (N, N '-diphenyl-N, N '-dinaphthyl-biphenyl to styrene support derivative P2 containing naphthalene ring and the poly- of cyano
Diamines) -2- cyano -2- (2- methoxyl group -4- (1- vinyl) -5- (2- ethyl hexyl oxy)) phenylethylene
Present embodiment the utility model has the advantages that
Present embodiment greatly expands the application range of PPV class material, poly- to styrene with cyano containing Long carbon chain
Polymer material is supportted, since its excellent heat resistance and mechanical performance cause the great interest of researcher.To have
The naphthalene nucleus and Long carbon chain that destroy bulk property is introduced into it is poly- in styrene support structure, be not only able to maintain it is original gather styrene is supportted
High thermal stability, and being capable of increasing its solubility enhances film forming ability, and this is not only advantageous to the thin-film electro of manufacture large area
Mutagens color device additionally provides electric activity center to promote the processing and application of electrochromic device；Present embodiment preparation
It is poly- that derivative is supportted using plane formula dialdehyde as monomer to styrene, the strong effect between polymer molecular chain can be effectively reduced
Power, increases the dissolubility of polymer, while being easily formed radical cation, shows the color different from middle condition.This reality
Applying in mode has very high performance resistant to high temperature to styrene support derivative containing naphthalene ring and the poly- of cyano, generally in nitrogen
Atmosphere under, decomposition temperature at 350 DEG C or more, be suitble to use in the devices.By present embodiment containing naphthalene ring and cyano
It is poly- that film is made to styrene support derivant material, there is no embrittlement and Fragmentation Phenomena on ITO substrate, is shown on ITO substrate
Good wet ability.This means that preparation supports derivant material with good to styrene containing naphthalene ring and the poly- of cyano
Film Formation and characteristics can be used to make the film of large area.Thin polymer film is able to maintain circulation during applying voltage
Circle has good stability, and is recycled 20 times or more and has good stability.
The poly- electrochromic property to styrene support derivative of present embodiment has following superior in practical applications
Property: (1) there is good electrochemical redox invertibity, is still able to maintain after tens redox cycles reversible；
(2) response time of color change is fast, after making alive, can change colour rapidly within 0.8 second；(3) variation of color is
Reversible；(4) color change high sensitivity；(5) there is higher cycle life；(6) material discoloration front and back has preferable chemistry steady
It is qualitative, under normal temperature and pressure, it may be stabilized in air.(7) derivative P1 is supportted to styrene containing naphthalene ring and the poly- of cyano
There is response to acidic and alkaline gas and picric acid；Derivative P2 is supportted to acid-base property gas to styrene containing naphthalene ring and the poly- of cyano
Body and explosive TNT, picric acid have response.
Specific embodiment 2: poly- preparation side to styrene support derivative of the present embodiment containing naphthalene ring and cyano
Method are as follows:
One, the monomer of the dialdehyde containing naphthalene ring is synthesized
By dicyano naphthalene nucleus diamine with except water-toluene mixes, logical nitrogen is vacuumized, then be placed in low-temp reaction kettle, cooled down
To -70 degrees Celsius, reducing agent diisobutyl aluminium hydride is added, 10min is stirred under -70 degrees celsius, closes cooling valve, keeps
Until temperature of reaction system time is warmed to room temperature, taking-up reaction system, which is placed in, to be continued to stir on magnetic stirring apparatus, then is successively added for stirring
Enter the ammonia spirit of acetone, ethyl acetate, ammonium chloride, obvious layering occurs in stirring to system, and upper layer is supernatant liquid, lower layer
There is solid precipitation, system is filtered, gained liquid revolving obtains dialdehyde monomer；
Two, it prepares and derivative is supportted to styrene containing naphthalene ring and the poly- of cyano
By dialdehyde monomer, solvent, 2- (2- ethyl hexyl oxy) -5- methoxyl group -1,4- benzene diacetonitrile containing cyano, tertiary fourth
Potassium alcoholate and catalyst tetrabutylammonium hydroxide are added in there-necked flask, are warming up to 50 DEG C and are stirred at reflux 20min or so, pour into after cooling
With in the methanol of acetic acid, refiltering and washing solid with methanol until methanol is without color, obtained solid is dried in vacuo,
It obtains supportting derivative to styrene containing naphthalene ring and the poly- of cyano；
Wherein the dicyano naphthalene nucleus diamine in step 1, diisobutyl aluminium hydride mass volume ratio be (1.0-1.5) g:
(2-3)mL；
Remove water-toluene and the volume mass ratio of dicyano naphthalene nucleus diamine in step 1 are 10mL:(1.0-1.5g)；
The mass volume ratio of acetone and dicyano naphthalene nucleus diamine in step 1 are as follows: (2-3) mL:(1.0-1.5g)；
The volume mass ratio of ethyl acetate and dicyano naphthalene nucleus diamine in step 1 are as follows: (2-3) m；:(1.0-1.5g)；
2- (2- ethyl hexyl oxy) -5- methoxyl group -1,4- benzene diacetonitrile of dialdehyde monomer, cyano-containing in step 2, uncle
Butanol potassium and the mass volume ratio of catalyst tetrabutylammonium hydroxide are 0.2g:0.15g:0.12g:5mL；
The volume mass ratio of solvent and dialdehyde monomer in step 2 is 20mL 0.2g；Solvent is the tert-butyl alcohol and tetrahydro furan
The 1:1 by volume that mutters is mixed；
Dicyano naphthalene nucleus diamine is N, N '-two (4- benzene first cyanogen)-N, N '-diphenyl-phenylenediamine or N, N '-two (4- benzene first
Cyanogen)-N, N '-diphenyl-benzidine.
Specific embodiment 3: present embodiment is unlike specific embodiment two: three being repeated in step 1
It is secondary to vacuumize logical nitrogen.Other are identical with embodiment two.
Specific embodiment 4: present embodiment is unlike specific embodiment two or three: stirring speed in step 1
Degree is 800r/min~900r/min.Other are identical as specific embodiment two or three.
Specific embodiment 5: present embodiment supports derivative as photoelectricity to styrene containing naphthalene ring and the poly- of cyano
The application of material.
Specific embodiment 6: present embodiment is unlike specific embodiment five: containing naphthalene ring and cyano
The poly- application method to styrene support derivative as photoelectric material: poly- support to styrene containing naphthalene ring and cyano is derived
Object is dissolved in organic solvent, is obtained supportting derivative solution to styrene containing naphthalene ring and the poly- of cyano, then will be contained naphthalene nucleus knot
Structure and the poly- of cyano carry out film to styrene support derivative on electro-conductive glass, obtain photoelectric material；Wherein organic solvent is
Tetrahydrofuran, chlorobenzene, N, N '-dimethyl acetamide or N, N '-dimethylformamide.Other and five phase of specific embodiment
Together.
Specific embodiment 7: present embodiment supports derivative as soda acid to styrene containing naphthalene ring and the poly- of cyano
The application of property gas detection material.
Specific embodiment 8: present embodiment is unlike specific embodiment seven: containing naphthalene ring and cyano
The poly- application method to styrene support derivative as acidic and alkaline gas detection material: by gathering to benzene containing naphthalene ring and cyano
Vinylene derivative is dissolved in organic solvent dichloromethane, is obtained poly- molten to styrene support derivative containing naphthalene ring and cyano
Liquid drips and supports derivative solution on silica gel plate to styrene containing naphthalene ring and the poly- of cyano, and drying removes solvent evaporation
It goes, observes and records fluorescence in the UV lamp, detect whether that there are soda acids using the variation of polymer fluorescent power on silica gel plate
Property gas, other are identical as with specific embodiment seven.
Present embodiment will be dissolved in organic solvent styrene support derivative containing naphthalene ring and the poly- of cyano, be contained
Naphthalene ring and the poly- of cyano support derivative solution to styrene, drip and spread out containing naphthalene ring and the poly- of cyano to styrene support
For biology on silica gel plate, solvent is evaporated removing by drying, is observed and recorded fluorescence in the UV lamp, is taken volatile bronsted lowry acids and bases bronsted lowry respectively
It is respectively placed in two weighing bottles, the poly- silica gel plate to styrene support derivative containing naphthalene ring and cyano will be loaded with and be placed in title
Measuring bottle mouth certain time, then puts and observes and records fluorescence in the UV lamp.Utilize the change of polymer fluorescent power on silica gel plate
Change to detect whether that there are acidic and alkaline gas.
Specific embodiment 9: present embodiment supports derivative in explosive to styrene containing naphthalene ring and the poly- of cyano
Application in detection.
Specific embodiment 10: present embodiment is unlike specific embodiment eight: containing naphthalene ring and cyano
The poly- application method that derivative analyte detection explosive is supportted to styrene are as follows: derive poly- support to styrene containing naphthalene ring and cyano
Object is dissolved in organic solvent, obtains supportting derivative solution to styrene containing naphthalene ring and the poly- of cyano, then will be to be detected molten
Drop, which is added on, supports in derivative solution styrene containing naphthalene ring and the poly- of cyano, is examined using the variation of solution fluorescence intensity
It surveys and whether there is explosive in solution；Wherein organic solvent is methylene chloride or THF.Other with eight phase of specific embodiment
Together.
Beneficial effects of the present invention are verified using following embodiment:
Embodiment one: the poly- structural formula for supportting derivative P1 to styrene containing naphthalene ring and cyano is as follows:
,
The integer that n is 3~10 in formula.
The present embodiment containing naphthalene ring and cyano it is poly- to styrene support derivative P1's the preparation method comprises the following steps:
One, N, N '-two (4- benzaldehyde)-N, N '-diphenyl-phenylenediamine are synthesized
By N, N '-two (4- benzene first cyanogen)-N, N '-diphenyl-phenylenediamine is mixed with water-toluene is removed, and is repeated and is taken out three times very
The logical nitrogen of sky, then be placed in low-temp reaction kettle, -70 degrees Celsius are cooled to, reducing agent diisobutyl aluminium hydride is added, -70 is Celsius
10min is stirred under the conditions of degree, closes cooling valve, is kept stirring and is warmed to room temperature up to temperature of reaction system returns, takes out reaction system
It is placed in and continues to stir on magnetic stirring apparatus, sequentially add the ammonia spirit of acetone, ethyl acetate, ammonium chloride, stirring to system
There is obvious layering, upper layer is supernatant liquid, and there is solid precipitation in lower layer, system is filtered, and gained liquid revolving obtains N,
N '-two (4- benzaldehyde)-N, N '-diphenyl-phenylenediamine；Wherein mixing speed is 800r/min~900r/min；
Two, poly- 1- (N, N '-diphenyl-N, N '-dinaphthyl-phenylenediamine) -2- cyano -2- (2- methoxyl group -4- (1- is prepared
Vinyl) -5- (2- ethyl hexyl oxy)) phenylethylene
By N, N '-two (4- benzaldehyde)-N, N '-diphenyl-phenylenediamine, solvent tertiary butanol and tetrahydrofuran THF contain cyanogen
2- (2- ethyl hexyl oxy) -5- methoxyl group -1,4- benzene diacetonitrile, potassium tert-butoxide and the catalyst tetrabutylammonium hydroxide of base are added
In there-necked flask, it is warming up to 50 DEG C and is stirred at reflux 20min or so, poured into the methanol with acetic acid after cooling, refilter and be used in combination
Methanol washs solid until obtained solid is dried in vacuo without color, obtains poly- 1- (N, N '-diphenyl-N, N '-two by methanol
Naphthalene-phenylenediamine) -2- cyano -2- (2- methoxyl group -4- (1- vinyl) -5- (2- ethyl hexyl oxy)) phenylethylene, i.e.,
Derivative P1 is supportted to styrene containing naphthalene ring and the poly- of cyano.
The wherein N in step 1, N '-two (4- benzene first cyanogen)-N, N '-diphenyl-phenylenediamine and diisobutyl aluminium hydride
Mass volume ratio is 1.0g:(2-3) mL；
Water-toluene and N, N '-two (4- benzene first cyanogen)-N, N '-diphenyl-phenylenediamine volume mass ratio are removed in step 1
For 10mL:(1.0-1.5g)；
Acetone and N in step 1, N '-two (4- benzene first cyanogen)-N, N '-diphenyl-phenylenediamine mass volume ratio are as follows:
(2-3)mL:1.0g；
Ethyl acetate and N in step 1, N '-two (4- benzene first cyanogen)-N, N '-diphenyl-phenylenediamine volume mass ratio
Are as follows: (2-3) mL:1.0g；
2- (the 2- ethyl hexyl oxygen of N in step 2, N '-two (4- benzaldehyde)-N, N '-diphenyl-phenylenediamine, cyano-containing
Base) -5- methoxyl group -1,4- benzene diacetonitrile, potassium tert-butoxide and catalyst tetrabutylammonium hydroxide mass volume ratio be 0.2g:
0.15g:0.12g:5mL；
The volume mass ratio of solvent and N in step 2, N '-two (4- benzaldehyde)-N, N '-diphenyl-phenylenediamine is
20mL:0.2g；Solvent is that 1:1 is mixed by volume for the tert-butyl alcohol and tetrahydrofuran.
It is as the preparation method of electrochromic material to styrene support derivative P1 containing naphthalene ring and the poly- of cyano: will
Poly- 1- (N, N '-diphenyl-N, N '-dinaphthyl-phenylenediamine) -2- cyano -2- (2- methoxyl group -4- (1- vinyl) -5-
(2- ethyl hexyl oxy)) phenylethylene is dissolved in organic solvent, obtain poly- 1- (N, N '-diphenyl-N, N '-dinaphthyl-benzene two
Amine) -2- cyano -2- (2- methoxyl group -4- (1- vinyl) -5- (2- ethyl hexyl oxy)) phenylethylene solution, then will
Poly- 1- (N, N '-diphenyl-N, N '-dinaphthyl-phenylenediamine) -2- cyano -2- (2- methoxyl group -4- (1- vinyl) -5-
(2- ethyl hexyl oxy)) phenylethylene carries out film on electro-conductive glass, obtain electrochromic material；Wherein organic solvent is four
Hydrogen furans, chlorobenzene, N, N '-dimethyl acetamide or N, N '-dimethylformamide.
It is as the preparation method of electroluminescent fluorescent materials to styrene support derivative P1 containing naphthalene ring and the poly- of cyano: will
Poly- 1- (N, N '-diphenyl-N, N '-dinaphthyl-phenylenediamine) -2- cyano -2- (2- methoxyl group -4- (1- vinyl) -5-
(2- ethyl hexyl oxy)) phenylethylene is dissolved in organic solvent, obtain poly- 1- (N, N '-diphenyl-N, N '-dinaphthyl-benzene two
Amine) -2- cyano -2- (2- methoxyl group -4- (1- vinyl) -5- (2- ethyl hexyl oxy)) phenylethylene solution, then will
Poly- 1- (N, N '-diphenyl-N, N '-dinaphthyl-phenylenediamine) -2- cyano -2- (2- methoxyl group -4- (1- vinyl) -5-
(2- ethyl hexyl oxy)) phenylethylene carries out film on electro-conductive glass, obtain electroluminescent fluorescent materials；Wherein organic solvent is four
Hydrogen furans, chlorobenzene, N, N '-dimethyl acetamide or N, N '-dimethylformamide.
The poly- method that derivative analyte detection explosive is supportted to styrene containing naphthalene ring and cyano are as follows: by poly- 1- (N, N '-two
Phenyl-N, N '-dinaphthyl-phenylenediamine) -2- cyano -2- (2- methoxyl group -4- (1- vinyl) -5- (2- ethyl hexyl oxygen
Base)) phenylethylene is dissolved in organic solvent, obtain poly- 1- (N, N '-diphenyl-N, N '-dinaphthyl-phenylenediamine) -2- cyano -2-
(2- methoxyl group -4- (1- vinyl) -5- (2- ethyl hexyl oxy)) phenylethylene solution, then solution to be detected is added dropwise
In by poly- 1- (N, N '-diphenyl-N, N '-dinaphthyl-phenylenediamine) -2- cyano -2- (2- methoxyl group -4- (1- vinyl) -
5- (2- ethyl hexyl oxy)) in phenylethylene solution, detected using the variation of solution fluorescence intensity in solution with the presence or absence of quick-fried
Fried object；Wherein organic solvent is methylene chloride or THF.
The poly- application side to styrene support derivative P1 as acidic and alkaline gas detection material containing naphthalene ring and cyano
Method are as follows: by poly- 1- (N, N '-diphenyl-N, N '-dinaphthyl-phenylenediamine) -2- cyano -2- (2- methoxyl group -4- (1- cyano vinyl
Base) -5- (2- ethyl hexyl oxy)) phenylethylene is dissolved in methylene chloride, obtain poly- 1- (N, N '-diphenyl-N, N '-dinaphthyl -
Phenylenediamine) -2- cyano -2- (2- methoxyl group -4- (1- vinyl) -5- (2- ethyl hexyl oxy)) phenylethylene solution, drop
One poly- 1- (N, N '-diphenyl-N, N '-dinaphthyl-phenylenediamine) -2- cyano -2- (2- methoxyl group -4- (1- vinyl)-of drop
5- (2- ethyl hexyl oxy)) for phenylethylene solution on silica gel plate, solvent is evaporated removing by drying, it observes and records in the UV lamp
Fluorescence detects whether that there are acidic and alkaline gas using the variation of polymer fluorescent power on silica gel plate.
Test poly- 1- (N, N '-diphenyl-N, N '-dinaphthyl-phenylenediamine) -2- cyano -2- (2- methoxyl group -4- (1- cyano
Vinyl) -5- (2- ethyl hexyl oxy)) phenylethylene dissolubility, the results are shown in Table 1, and solubility is with 10 milligrams of samples
It is dissolved in and measures in 1 milliliter of solution.++, dissolve in room temperature.+, it dissolves by heating.The part of+- during heating is solvable.It is insoluble
Solution.As shown in Table 1, the present embodiment has good dissolubility to styrene support derivative containing naphthalene ring and the poly- of cyano.
Table 1
Embodiment two: the poly- structural formula for supportting derivative P2 to styrene containing naphthalene ring and cyano is as follows:
,
The integer that n is 3~10 in formula.
Containing naphthalene ring and cyano it is poly- to styrene support derivative P2's the preparation method comprises the following steps:
One, N, N '-two (4- benzaldehyde)-N, N '-diphenyl-benzidine are synthesized
By N, N '-two (4- benzene first cyanogen)-N, N '-diphenyl-benzidine is repeated and takes out three times with except water-toluene mixes
Vacuum leads to nitrogen, then is placed in low-temp reaction kettle, is cooled to -70 degrees Celsius, reducing agent diisobutyl aluminium hydride is added, -70 take the photograph
10min is stirred under the conditions of family name's degree, closes cooling valve, is kept stirring and is warmed to room temperature up to temperature of reaction system returns, takes out reactant
System, which is placed in, to continue to stir on magnetic stirring apparatus, sequentially adds the ammonia spirit of acetone, ethyl acetate, ammonium chloride, stirring to body
There is obvious layering in system, and upper layer is supernatant liquid, and there is solid precipitation in lower layer, system is filtered, and gained liquid revolving obtains
N, N '-two (4- benzaldehyde)-N, N '-diphenyl-phenylenediamine/N, N '-two (4- benzaldehyde)-N, N '-diphenyl-benzidine,
Wherein the mixing speed is 800r/min~900r/min.
Two, poly- 1- (N, N '-diphenyl-N, N '-dinaphthyl-benzidine) -2- cyano -2- (2- methoxyl group -4- is prepared
(1- vinyl) -5- (2- ethyl hexyl oxy)) phenylethylene
By N, N '-two (4- benzaldehyde)-N, N '-diphenyl-benzidine, solvent tertiary butanol and tetrahydrofuran THF contain
2- (2- ethyl hexyl oxy) -5- methoxyl group -1,4- benzene diacetonitrile, potassium tert-butoxide and the catalyst tetrabutylammonium hydroxide of cyano add
Enter in there-necked flask, is warming up to 50 DEG C and is stirred at reflux 20min or so, pour into the methanol with acetic acid, refiltered simultaneously after cooling
Solid is washed with methanol until obtained solid is dried in vacuo without color, obtains poly- 1- (N, N '-diphenyl-N, N '-by methanol
Dinaphthyl-benzidine) -2- cyano -2- (2- methoxyl group -4- (1- vinyl) -5- (2- ethyl hexyl oxy)) phenyl second
Alkene supports derivative P2 to styrene containing naphthalene ring and the poly- of cyano.
The wherein N in step 1, N '-two (4- benzene first cyanogen)-N, N '-diphenyl-benzidine and diisobutyl aluminium hydride
Mass volume ratio be 1.5g:(2-3) mL；
Water-toluene and N, N '-two (4- benzene first cyanogen)-N, N '-diphenyl-benzidine volume mass are removed in step 1
Than for 10mL:1.5g；
Acetone and N in step 1, N '-two (4- benzene first cyanogen)-N, N '-diphenyl-benzidine mass volume ratio are as follows:
(2-3)mL:1.5g；
Ethyl acetate and N in step 1, N '-two (4- benzene first cyanogen)-N, N '-diphenyl-benzidine volume mass
Than are as follows: (2-3) mL:1.5g；
N in step 2, N '-two (4- benzene first cyanogen)-N, 2- (the 2- ethyl hexyl of N '-diphenyl-benzidine, cyano-containing
Oxygroup) -5- methoxyl group -1,4- benzene diacetonitrile, potassium tert-butoxide and catalyst tetrabutylammonium hydroxide mass volume ratio be 0.2g:
0.15g:0.12g:5mL；
Solvent and N in step 2, N '-two (4- benzene first cyanogen)-N, N '-diphenyl-benzidine volume mass ratio are
20mL:0.2g；Solvent is that 1:1 is mixed by volume for the tert-butyl alcohol and tetrahydrofuran.
It is as the preparation method of electrochromic material to styrene support derivative P2 containing naphthalene ring and the poly- of cyano: will
Poly- 1- (N, N '-diphenyl-N, N '-dinaphthyl-benzidine) -2- cyano -2- (2- methoxyl group -4- (1- vinyl) -5-
(2- ethyl hexyl oxy)) phenylethylene is dissolved in organic solvent, obtain poly- 1- (N, N '-diphenyl-N, N '-dinaphthyl-biphenyl two
Amine) -2- cyano -2- (2- methoxyl group -4- (1- vinyl) -5- (2- ethyl hexyl oxy)) phenylethylene solution, then will
Poly- 1- (N, N '-diphenyl-N, N '-dinaphthyl-benzidine) -2- cyano -2- (2- methoxyl group -4- (1- vinyl) -5-
(2- ethyl hexyl oxy)) phenylethylene carries out film on electro-conductive glass, obtain electrochromic material；Organic solvent is tetrahydro furan
It mutters, chlorobenzene, N, N '-dimethyl acetamide or N, N '-dimethylformamide.
It is as the preparation method of electroluminescent fluorescent materials to styrene support derivative P2 containing naphthalene ring and the poly- of cyano: will
Poly- 1- (N, N '-diphenyl-N, N '-dinaphthyl-benzidine) -2- cyano -2- (2- methoxyl group -4- (1- vinyl) -5-
(2- ethyl hexyl oxy)) phenylethylene is dissolved in organic solvent, obtain poly- 1- (N, N '-diphenyl-N, N '-dinaphthyl-biphenyl two
Amine) -2- cyano -2- (2- methoxyl group -4- (1- vinyl) -5- (2- ethyl hexyl oxy)) phenylethylene solution, then will
Poly- 1- (N, N '-diphenyl-N, N '-dinaphthyl-benzidine) -2- cyano -2- (2- methoxyl group -4- (1- vinyl) -5-
(2- ethyl hexyl oxy)) phenylethylene carries out film on electro-conductive glass, obtain electroluminescent fluorescent materials；Wherein organic solvent is four
Hydrogen furans, chlorobenzene, N, N '-dimethyl acetamide or N, N '-dimethylformamide.
The poly- method to styrene support derivative P2 detection explosive containing naphthalene ring and cyano are as follows: by poly- 1- (N, N '-
Diphenyl-N, N '-dinaphthyl-benzidine) -2- cyano -2- (2- methoxyl group -4- (1- vinyl) -5- (2- ethyl hexyl
Oxygroup)) phenylethylene is dissolved in organic solvent, obtain poly- 1- (N, N '-diphenyl-N, N '-dinaphthyl-benzidine) -2- cyanogen
Base -2- (2- methoxyl group -4- (1- vinyl) -5- (2- ethyl hexyl oxy)) phenylethylene solution, then will be to be detected molten
Drop is added on poly- 1- (N, N '-diphenyl-N, N '-dinaphthyl-benzidine) -2- cyano -2- (2- methoxyl group -4- (1- cyano
Vinyl) -5- (2- ethyl hexyl oxy)) in phenylethylene solution, the variation using solution fluorescence intensity is to detect in solution
No there are explosives, and wherein organic solvent is methylene chloride or THF.
The poly- application side to styrene support derivative P2 as acidic and alkaline gas detection material containing naphthalene ring and cyano
Method are as follows: by poly- 1- (N, N '-diphenyl-N, N '-dinaphthyl-benzidine) -2- cyano -2- (2- methoxyl group -4- (1- cyano second
Alkenyl) -5- (2- ethyl hexyl oxy)) phenylethylene is dissolved in methylene chloride, obtain poly- 1- (N, N '-diphenyl-N, N '-dinaphthyl
Base-benzidine) -2- cyano -2- (2- methoxyl group -4- (1- vinyl) -5- (2- ethyl hexyl oxy)) phenylethylene is molten
Liquid drips poly- 1- (N, N '-diphenyl-N, N '-dinaphthyl-benzidine) -2- cyano -2- (2- methoxyl group -4- (1- cyano
Vinyl) -5- (2- ethyl hexyl oxy)) phenylethylene solution is on silica gel plate, and solvent is evaporated removing by drying, in the UV lamp
Fluorescence is observed and recorded, detects whether that there are acidic and alkaline gas using the variation of polymer fluorescent power on silica gel plate.
Test poly- 1- (N, N '-diphenyl-N, N '-dinaphthyl-benzidine) -2- cyano -2- (2- methoxyl group -4- (1- cyanogen
Base vinyl) -5- (2- ethyl hexyl oxy)) phenylethylene dissolubility, the results are shown in Table 2, and solubility is with 10 milligrams of samples
Product, which are dissolved in, to be measured in 1 milliliter of solution.++, dissolve in room temperature.+, it dissolves by heating.The part of+- during heating is solvable.It is insoluble
Solution.As shown in Table 2, the present embodiment has good dissolubility to styrene support derivative containing naphthalene ring and the poly- of cyano.
Table 2
By poly- 1- (N, N '-diphenyl-N, N '-dinaphthyl-phenylenediamine) -2- cyano -2- (2- methoxyl group -4- (1- cyano second
Alkenyl) -5- (2- ethyl hexyl oxy)) phenylethylene and poly- 1- (N, N '-diphenyl-N, N '-dinaphthyl-benzidine) -2- cyanogen
Base -2- (2- methoxyl group -4- (1- vinyl) -5- (2- ethyl hexyl oxy)) phenylethylene coating film forming, to its performance into
Row test:
Fig. 1 is the poly- INFRARED SPECTRUM that derivative is supportted to styrene containing naphthalene ring and cyano prepared by embodiment one and two
Figure；From fig. 1, it can be seen that in 2220-2250cm-1The characteristic absorption peak at place, corresponding to the stretching vibration peak of C-N key in cyano,
2915-2918cm-1Neighbouring peak is the stretching vibration peak of methyl, in 1670-1690cm-1The characteristic peak at place is stretching for C=C key
Contracting vibration peak.
Fig. 2 is the poly- proton magnetic spectrum that derivative P1 is supportted to styrene containing naphthalene ring and cyano prepared by embodiment one
Figure；Fig. 3 is the poly- hydrogen nuclear magnetic spectrogram that derivative P2 is supportted to styrene containing naphthalene ring and cyano prepared by embodiment two；From figure
2 and 3 it is found that δ=7.11-8.18ppm is the chemical shift of H on phenyl ring, specifically as figure indicates.
Fig. 4 is the poly- cyclic voltammetric that derivative P1 is supportted to styrene containing naphthalene ring and cyano prepared by embodiment one
Figure；Fig. 5 is the poly- cyclic voltammogram that derivative P2 is supportted to styrene containing naphthalene ring and cyano prepared by embodiment two；From figure
4 and Fig. 5 is easily oxidized reduction it is found that it has lower initial potential and reduction potential, there are two oxidation peak and theoretical speculates
As a result it is consistent.
Fig. 6 is the poly- electrochromism that derivative P1 is supportted to styrene containing naphthalene ring and cyano prepared by embodiment one
Figure；Fig. 7 is the poly- electrochromism figure that derivative P2 is supportted to styrene containing naphthalene ring and cyano prepared by embodiment two；From figure
6 and Fig. 7 has suction to styrene support derivative P1 containing naphthalene ring and the poly- of cyano it is found that before not applying voltage at 422nm
Peak is received, when applied voltage is from 0.0V to 1.7V, absorption peak is gradually increasing at 422nm, is occurred newly at 922nm and 1285nm
Absorption peak is simultaneously gradually increasing；Electrochromic color is from light yellow to light blue again to navy blue；Containing naphthalene ring and cyano
It is poly- to have absorption peak at 366nm before no applied voltage to styrene support derivative P2, when applied voltage is from 0.0V to 1.8V,
Absorption peak is gradually reduced at 366nm, is occurred new absorption peak at 788nm and is gradually increasing, occurs new suction at 1370nm
It receives peak and first rises and decline electrochromic color afterwards and eventually become navy blue from light yellow to light blue.
Fig. 8 is the poly- electroluminescent fluorescent that derivative P1 is supportted to styrene containing naphthalene ring and cyano prepared by embodiment one
Figure；Fig. 9 is the poly- electroluminescent fluorescent figure that derivative P2 is supportted to styrene containing naphthalene ring and cyano prepared by embodiment two；Not
Before applying voltage, fluorescence intensity reaches highest level, and as applied voltage increases, the fluorescence intensity of polymer P 1 is gradually reduced most
Zero, the P2 fluorescence intensity that almost levels off to afterwards is gradually reduced.
Figure 10 is the poly- thermal weight loss that derivative is supportted to styrene containing naphthalene ring and cyano prepared by embodiment one and two
Curve graph；As can be seen from Figure 10, what prepared by embodiment one supports derivative about 400 to styrene containing naphthalene ring and the poly- of cyano
DEG C or so start a large amount of weightless, P2 is when temperature is at 423 DEG C, weight loss 5%, and when temperature is 508 DEG C, weight loss is
10%；When temperature is 604 DEG C, weight loss 20%, when temperature reaches 800 DEG C embodiment one prepare containing naphthalene ring and
The poly- of cyano is 64% to styrene support derivative carbon residual volume；P1 is when temperature is at 353 DEG C, weight loss 5%, when temperature is
At 425 DEG C, weight loss 10%；When temperature is 497 DEG C, weight loss 20%, when temperature reaches 800 DEG C, embodiment one is made
Standby is 61% to styrene support derivative carbon residual volume containing naphthalene ring and the poly- of cyano.With preferable high temperature resistance.
Figure 11 is that the poly- of the cyano containing naphthalene ring prepared by embodiment one and two supports derivative to volatile acid to styrene
The fluorogram of alkali gas response；It obviously dies down when with ten seconds post-consumer polymer fluorescence of sour gas contact number as seen from Figure 11,
The fluorescence intensity with ten seconds polymer of alkaline gas contact number is gradually replied on this basis.
Figure 12 is ringing to styrene support derivative P1 to picric acid containing naphthalene ring and the poly- of cyano for the preparation of embodiment one
The fluorogram answered；Figure 13 supports derivative P2 to picric acid to styrene containing naphthalene ring and the poly- of cyano for prepared by embodiment two
The fluorogram of response；Increase with bitter taste acid concentration can be seen that by Figure 12 and 13, the fluorescence intensity of polymer solution is gradually
Weaken.
Figure 14 is responding to styrene support derivative P2 to TNT containing naphthalene ring and the poly- of cyano for the preparation of embodiment two
Fluorogram；As seen from Figure 14 with the increase of TNT concentration, the fluorescence intensity of polymer solution gradually weakens.
By above-mentioned test it is found that manufactured in the present embodiment support derivative to styrene containing naphthalene ring and the poly- of cyano with flat
The dialdehyde-based naphthalene nucleus of face formula and reacting dicyanobenzenes for the company containing long alkoxy are made, and polymer molecular chain can be effectively reduced
Between strong effect power, increase the dissolubility of polymer, at the same be easily formed radical cation show be different from neutrality
State.There is very high performance resistant to high temperature to styrene support derivative containing naphthalene ring and the poly- of cyano in the present invention, generally exists
Under the atmosphere of nitrogen, decomposition temperature is suitble to use in the devices at 350 DEG C or more.By the present invention containing naphthalene ring and cyano
It is poly- that film is made to styrene support derivant material, there is no big clustering phenomena and Fragmentation Phenomena on ITO substrate, is served as a contrast in ITO
Good wet ability is also shown on bottom.This means that PPV material has good film Formation and characteristics, can be used to make big face
Long-pending film.After application of a voltage, the transmitance of film still can achieve 40%, and transparency is relatively good, and apply voltage
During thin polymer film be able to maintain circulating ring and have good stability, be recycled 20 times or more and transparency be constant.
The poly- electrochromic property to styrene support derivative of the present embodiment has following superiority in practical applications:
(1) there is good electrochemical redox invertibity, be still able to maintain after tens redox cycles reversible；(2)
The response time of color change is fast, after making alive, can change colour rapidly within 0.8 second；(3) variation of color is reversible
's；(4) color change high sensitivity；(5) there is higher cycle life；(6) there is preferable chemical stability in material discoloration front and back,
Under normal temperature and pressure, it may be stabilized in air.(7) derivative P1 is supportted to soda acid to styrene containing naphthalene ring and the poly- of cyano
Property gas and picric acid have response；Poly- containing naphthalene ring and cyano is to styrene support derivative P2 to acidic and alkaline gas and quick-fried
Fried object TNT, picric acid have response.
Claims (10)
1. poly- containing naphthalene ring and cyano supports derivative to styrene, it is characterised in that poly- to benzene containing naphthalene ring and cyano
Vinylene derivative is poly- poly- pair to styrene support derivative P1 or containing naphthalene ring and cyano containing naphthalene ring and cyano
Styrene supports derivative P2；
The poly- structural formula for supportting derivative P1 to styrene wherein containing naphthalene ring and cyano is as follows:
,
The integer that n is 3~10 in formula；
It is wherein poly- as follows to styrene support derivative P2 structural formula containing naphthalene ring and cyano:
,
The integer that n is 3~10 in formula.
2. preparing the poly- method to styrene support derivative containing naphthalene ring and cyano as described in claim 1, feature
Be containing naphthalene ring and cyano it is poly- to styrene support derivative the preparation method comprises the following steps:
One, the monomer of the dialdehyde containing naphthalene ring is synthesized
By dicyano naphthalene nucleus diamine with except water-toluene mixes, logical nitrogen is vacuumized, then be placed in low-temp reaction kettle, be cooled to -70
Degree Celsius, reducing agent diisobutyl aluminium hydride is added, 10min is stirred under -70 degrees celsius, closes cooling valve, is kept stirring
It is warmed to room temperature until temperature of reaction system returns, takes out reaction system and be placed in and continue to stir on magnetic stirring apparatus, sequentially add third
Ketone, ethyl acetate, ammonium chloride ammonia spirit, there is obvious layering in stirring to system, and upper layer is supernatant liquid, and lower layer has solid
Body is precipitated, and system is filtered, and gained liquid revolving obtains dialdehyde monomer；
Two, it prepares and derivative is supportted to styrene containing naphthalene ring and the poly- of cyano
By dialdehyde monomer, solvent, 2- (2- ethyl hexyl oxy) -5- methoxyl group -1,4- benzene diacetonitrile, potassium tert-butoxide containing cyano
And catalyst tetrabutylammonium hydroxide is added in there-necked flask, is warming up to 50 DEG C and is stirred at reflux 20min or so, pours into after cooling and use second
In the methanol of acid acidification, refilters and wash solid with methanol until obtained solid is dried in vacuo, obtains without color by methanol
Derivative is supportted to styrene containing naphthalene ring and the poly- of cyano；
Wherein the dicyano naphthalene nucleus diamine in step 1, diisobutyl aluminium hydride mass volume ratio be (1.0-1.5) g:(2-3)
mL；
Remove water-toluene and the volume mass ratio of dicyano naphthalene nucleus diamine in step 1 are 10mL:(1.0-1.5g)；
The mass volume ratio of acetone and dicyano naphthalene nucleus diamine in step 1 are as follows: (2-3) mL:(1.0-1.5g)；
The volume mass ratio of ethyl acetate and dicyano naphthalene nucleus diamine in step 1 are as follows: (2-3) m；:(1.0-1.5g)；
2- (2- ethyl hexyl oxy) -5- methoxyl group -1,4- benzene diacetonitrile, the tert-butyl alcohol of dialdehyde monomer, cyano-containing in step 2
Potassium and the mass volume ratio of catalyst tetrabutylammonium hydroxide are 0.2g:0.15g:0.12g:5mL；
The volume mass ratio of solvent and dialdehyde monomer in step 2 is 20mL 0.2g；Solvent is that the tert-butyl alcohol and tetrahydrofuran are pressed
Volume ratio 1:1 is mixed；
Dicyano naphthalene nucleus diamine is N, N '-two (4- benzene first cyanogen)-N, N '-diphenyl-phenylenediamine or N, N '-two (4- benzene first cyanogen)-
N, N '-diphenyl-benzidine.
3. the poly- preparation method to styrene support derivative according to claim 2 containing naphthalene ring and cyano, special
Sign is to be repeated in step 1 vacuumizes logical nitrogen three times.
4. the poly- preparation method to styrene support derivative according to claim 2 containing naphthalene ring and cyano, special
Sign is in step 1 that mixing speed is 800r/min~900r/min.
5. the poly- application to styrene support derivative containing naphthalene ring and cyano as described in claim 1, it is characterised in that
The poly- application to styrene support derivative as photoelectric material containing naphthalene ring and cyano.
6. the poly- application to styrene support derivative according to claim 5 containing naphthalene ring and cyano, feature exist
In the poly- application method to styrene support derivative as photoelectric material containing naphthalene ring and cyano: naphthalene ring and cyanogen will be contained
The poly- of base is dissolved in organic solvent styrene support derivative, obtains supportting derivative to styrene containing naphthalene ring and the poly- of cyano
Then solution will carry out film to styrene support derivative containing naphthalene ring and the poly- of cyano on electro-conductive glass, obtain photoelectricity
Material；Wherein organic solvent is tetrahydrofuran, chlorobenzene, N, N '-dimethyl acetamide or N, N '-dimethylformamide.
7. the poly- application to styrene support derivative containing naphthalene ring and cyano as described in claim 1, it is characterised in that
The poly- application to styrene support derivative as acidic and alkaline gas detection material containing naphthalene ring and cyano.
8. the poly- application to styrene support derivative according to claim 7 containing naphthalene ring and cyano, feature exist
In the poly- application method to styrene support derivative as acidic and alkaline gas detection material containing naphthalene ring and cyano are as follows: will contain
Naphthalene ring and the poly- of cyano are dissolved in organic solvent dichloromethane styrene support derivative, obtain containing naphthalene ring and cyano
It is poly- derivative solution is supportted to styrene, drip and derivative solution is supportted in silica gel to styrene containing naphthalene ring and gathering for cyano
On plate, solvent is evaporated in drying to be removed, and is observed and recorded fluorescence in the UV lamp, is utilized the change of polymer fluorescent power on silica gel plate
Change to detect whether that there are acidic and alkaline gas.
9. the poly- application to styrene support derivative containing naphthalene ring and cyano as described in claim 1, it is characterised in that
The poly- application to styrene support derivative in explosive detection containing naphthalene ring and cyano.
10. the poly- application to styrene support derivative according to claim 9 containing naphthalene ring and cyano, feature exist
In the poly- application method for supportting derivative analyte detection explosive to styrene containing naphthalene ring and cyano are as follows: naphthalene ring and cyanogen will be contained
The poly- of base is dissolved in organic solvent styrene support derivative, obtains supportting derivative to styrene containing naphthalene ring and the poly- of cyano
Then solution to be measured is added dropwise in poly- in styrene support derivative solution, is examined using the variation of solution fluorescence intensity by solution
It surveys and whether there is explosive in solution, wherein organic solvent is methylene chloride or THF.
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| CN1554726A (en) * | 2003-12-27 | 2004-12-15 | 复旦大学 | Polymer material for electroluminescent device and its preparing method |
| CN108690197A (en) * | 2018-05-09 | 2018-10-23 | 黑龙江大学 | Polyimide derivatives and its preparation method and application containing fluorine-triphenylamine structure and naphthalimide fluorophore |
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| CN1554726A (en) * | 2003-12-27 | 2004-12-15 | 复旦大学 | Polymer material for electroluminescent device and its preparing method |
| CN108690197A (en) * | 2018-05-09 | 2018-10-23 | 黑龙江大学 | Polyimide derivatives and its preparation method and application containing fluorine-triphenylamine structure and naphthalimide fluorophore |
Non-Patent Citations (1)
| Title |
|---|
| 张力等: "用于光伏电池上的新型高分子PPV材料", 《功能高分子学报》 * |
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