CN104961753A - Anthracene-containing 8-hydroxyquinoline zinc complex mononuclear crystal with scroll structure, and preparation method and applications thereof - Google Patents
Anthracene-containing 8-hydroxyquinoline zinc complex mononuclear crystal with scroll structure, and preparation method and applications thereof Download PDFInfo
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- CN104961753A CN104961753A CN201510263998.9A CN201510263998A CN104961753A CN 104961753 A CN104961753 A CN 104961753A CN 201510263998 A CN201510263998 A CN 201510263998A CN 104961753 A CN104961753 A CN 104961753A
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- crystal
- anthracene
- monokaryon
- complex
- oxine
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- 239000013078 crystal Substances 0.000 title claims abstract description 71
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 title claims abstract description 51
- 238000002360 preparation method Methods 0.000 title abstract description 9
- DLJHXMRDIWMMGO-UHFFFAOYSA-N quinolin-8-ol;zinc Chemical compound [Zn].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 DLJHXMRDIWMMGO-UHFFFAOYSA-N 0.000 title abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 42
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 26
- 238000006243 chemical reaction Methods 0.000 claims abstract description 17
- 239000003446 ligand Substances 0.000 claims abstract description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000000463 material Substances 0.000 claims abstract description 15
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract description 13
- 150000003751 zinc Chemical class 0.000 claims abstract description 10
- 239000000126 substance Substances 0.000 claims abstract description 4
- 239000011701 zinc Substances 0.000 claims description 48
- -1 anthracene oxine class Chemical class 0.000 claims description 36
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 25
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 18
- 229920002554 vinyl polymer Polymers 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 14
- 239000007787 solid Substances 0.000 claims description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- 239000012153 distilled water Substances 0.000 claims description 12
- 238000010992 reflux Methods 0.000 claims description 12
- 229910052751 metal Inorganic materials 0.000 claims description 9
- 238000010189 synthetic method Methods 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- 230000015572 biosynthetic process Effects 0.000 claims description 7
- 238000002156 mixing Methods 0.000 claims description 7
- 239000012074 organic phase Substances 0.000 claims description 6
- 238000010025 steaming Methods 0.000 claims description 6
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- 238000003786 synthesis reaction Methods 0.000 claims description 5
- 239000003480 eluent Substances 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 239000003208 petroleum Substances 0.000 claims description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 4
- NBYLBWHHTUWMER-UHFFFAOYSA-N 2-Methylquinolin-8-ol Chemical compound C1=CC=C(O)C2=NC(C)=CC=C21 NBYLBWHHTUWMER-UHFFFAOYSA-N 0.000 claims description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 3
- 239000000090 biomarker Substances 0.000 claims description 3
- 238000000605 extraction Methods 0.000 claims description 3
- 239000000706 filtrate Substances 0.000 claims description 3
- 125000006850 spacer group Chemical group 0.000 claims description 3
- RXBXBWBHKPGHIB-UHFFFAOYSA-L zinc;diperchlorate Chemical group [Zn+2].[O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O RXBXBWBHKPGHIB-UHFFFAOYSA-L 0.000 claims description 3
- 206010070834 Sensitisation Diseases 0.000 claims description 2
- YMNKUHIVVMFOFO-UHFFFAOYSA-N anthracene-9-carbaldehyde Chemical compound C1=CC=C2C(C=O)=C(C=CC=C3)C3=CC2=C1 YMNKUHIVVMFOFO-UHFFFAOYSA-N 0.000 claims description 2
- 150000001454 anthracenes Chemical class 0.000 claims description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
- 238000007789 sealing Methods 0.000 claims description 2
- 238000001291 vacuum drying Methods 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- 235000005074 zinc chloride Nutrition 0.000 claims description 2
- 239000011592 zinc chloride Substances 0.000 claims description 2
- 239000000243 solution Substances 0.000 abstract description 22
- 238000004220 aggregation Methods 0.000 abstract description 6
- 230000002776 aggregation Effects 0.000 abstract description 6
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 abstract description 6
- 238000005401 electroluminescence Methods 0.000 abstract description 5
- 239000011259 mixed solution Substances 0.000 abstract description 2
- IJXGUBDEUBBSIT-CCEZHUSRSA-N 2-[(E)-2-anthracen-9-ylethenyl]quinolin-8-ol Chemical compound C1=CC=CC2=CC3=CC=CC=C3C(=C12)/C=C/C1=NC2=C(C=CC=C2C=C1)O IJXGUBDEUBBSIT-CCEZHUSRSA-N 0.000 abstract 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 abstract 1
- 238000002372 labelling Methods 0.000 abstract 1
- 229960003540 oxyquinoline Drugs 0.000 abstract 1
- 238000000034 method Methods 0.000 description 8
- 239000002184 metal Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 238000004448 titration Methods 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical group [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 230000005284 excitation Effects 0.000 description 3
- MNCMBBIFTVWHIP-UHFFFAOYSA-N 1-anthracen-9-yl-2,2,2-trifluoroethanone Chemical group C1=CC=C2C(C(=O)C(F)(F)F)=C(C=CC=C3)C3=CC2=C1 MNCMBBIFTVWHIP-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 238000002441 X-ray diffraction Methods 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 230000000536 complexating effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000002411 thermogravimetry Methods 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- CBMCZKMIOZYAHS-NSCUHMNNSA-N [(e)-prop-1-enyl]boronic acid Chemical compound C\C=C\B(O)O CBMCZKMIOZYAHS-NSCUHMNNSA-N 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000005577 anthracene group Chemical group 0.000 description 1
- XJDFBLQCLSBCGQ-UHFFFAOYSA-N anthracene-1-carbaldehyde Chemical compound C1=CC=C2C=C3C(C=O)=CC=CC3=CC2=C1 XJDFBLQCLSBCGQ-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000007421 fluorometric assay Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229910000765 intermetallic Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 150000001455 metallic ions Chemical class 0.000 description 1
- 238000004776 molecular orbital Methods 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000003252 repetitive effect Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000005201 scrubbing Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 230000003245 working effect Effects 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/003—Compounds containing elements of Groups 2 or 12 of the Periodic Table without C-Metal linkages
-
- 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
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/381—Metal complexes comprising a group IIB metal element, e.g. comprising cadmium, mercury or zinc
-
- 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
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- 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
- C09K2211/18—Metal complexes
- C09K2211/188—Metal complexes of other metals not provided for in one of the previous groups
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention provides an anthracene-containing 8-hydroxyquinoline zinc complex mononuclear crystal with a scroll structure, and a preparation method and applications thereof. The preparation method comprises following steps: (E)-2-[2-(9-anthryl) ethenyl]-8-hydroxyquinoline is dissolved in N, N-dimethyl formamide, methanol is added dropwise, pyridine is added dropwise, and finally a N, N-dimethyl formamide solution containing a zinc salt is added; an obtained mixed solution is delivered into a sealed container, and reaction is carried out at 65 to 85 DEG C until crystal is precipitated; an obtained solution is filtered, and crystal is washed with methanol, and is dried. The anthracene-containing 8-hydroxyquinoline zinc complex is high in luminescent intensity and thermal stability, and long in fluorescent lifetime; possesses potential economic value in preparation of luminescent materials or photoelectric luminescent devices. The anthracene-containing 8-hydroxyquinoline ligand and the complex thereof both possess aggregation-induced emission performance, and can be widely applied to the fields such as chemical sensing, biosensing, bio-labeling, electroluminescence, and logic gate devices.
Description
Technical field
The present invention relates to metal complexes field, more specifically, relate to one and have twist structured containing anthracene oxine class Zn complex monokaryon crystal and its preparation method and application.
Background technology
Organic electroluminescence device (OLED) has that visual angle is wide, low in energy consumption, fast response time, technique are simple, can realize the advantages such as total colouring, therefore has broad application prospects in flat pannel display and solid light source field.Since the C.W.Tang reported first of the U.S. in 1987 adopts three (oxine) aluminium (Alq3) to be manufactured with organic electroluminescence devices, numerous new Organic Electro Luminescent Materials (OELM, OrganicElectroluminescence Material) is successfully synthesized to meet the requirement improving OLED performance.
Luminescent material is the material finally bearing lighting function in device, and therefore the luminous efficiency of luminescent material, the character such as luminescent lifetime and luminescent chromaticity all have a direct impact to the performance of OLED.Following condition should be possessed: 1) there is high efficiency solid state fluorescence, without significant concn Quenching as the luminescent material in OLED; 2) there is good chemical stability and thermostability, do not react with electrode and carrier transmission material; 3) easily fine and close noncrystalline membrane is formed and not easily crystallization; 4) there is suitable emission wavelength; 5) there is good conductive characteristic and certain carrier transport ability.
And there is twist structured luminescent material because having aggregation-induced emission (AIE) phenomenon, extensively concerned in recent years.Twist structure specific to this kind of luminescent material, make there is strong rigidity in its molecule, and have high efficiency solid state fluorescence and high fluorescence quantum yield, AIE active material also improves fluorescent emission simultaneously, extends the fluorescence lifetime of luminescent material.And twist structure has higher mobility, high carrier mobility has larger potentiality and research space.
Anthracene, condensed-nuclei aromatics compounds, has many excellent features:; Strong π-electron delocalized energy; Blue light-emitting; Good thermostability; Higher fluorescence quantum efficiency; Long fluorescence lifetime; Under electric field induce, easily polarization waits and is widely used outside.
In numerous OELM, the properties due to oxine metal complexes (Mqn) is better than the OELM of other type, but obtained by existing Mqn device luminous intensity and still can not reach the practical stage work-ing life.Because the spatial configuration of molecules of Mqn can affect its various material properties comprising luminescent properties.But the synthetic method of Mqn and the research deficiency of method of purification, can not meet the requirement of its commercialization scale operation, be unfavorable for the reduction of OLED production cost at present.Therefore the luminescent material that a kind of performance is good, cost is lower, space structure is clear and definite is developed significant.
Summary of the invention
The present invention, for overcoming above-mentioned prior art defect, provides one to have twist structured containing anthracene oxine class Zn complex monokaryon crystal.Described have twist structuredly containing anthracene oxine class Zn complex monokaryon crystal, there is good luminous intensity, thermostability and good fluorescence lifetime.
Another goal of the invention of the present invention is, provides the preparation method of described monokaryon crystal and ligand L.
Another goal of the invention of the present invention is, provides the application of described monokaryon crystal and ligand L.
For solving the problems of the technologies described above, the technical solution used in the present invention is:
One has twist structured containing anthracene oxine class Zn complex monokaryon crystal, and be that metal center and ligand L and pyridine carry out coordination and obtain with Zn, its molecular formula is ZnL
2py; Described ligand L is (E)-2-[2-(9-anthryl) vinyl]-oxine, and its molecular structure is:
py is pyridine;
The described structure containing anthracene oxine class Zn complex monokaryon crystal is as follows:
Described Zn carries out coordination with containing anthracene part (E)-2-[2-(1-anthryl) vinyl]-oxine, on the one hand, enhances the transfer ability of electronics in skeleton, and reduces the energy of transition of electron between metal and part; On the other hand, the introducing of anthryl in part, forms large conjugate planes, reduces the energy of system, makes described monokaryon crystal have stronger luminous intensity.
The elementary cell of described monokaryon crystal comprises 1 central atom Zn, 2 ligand L, 1 Pyridine Molecules, and Zn (II) atom takes pentacoordinate mode, forms the octahedra geometric configuration of a distortion.
The crystal parameters of described monokaryon crystal is as follows: belong to oblique system, and spacer is C12/c 1 (15), Z=4,
b=9.0180 (8) nm, c=19.2691 (17) nm, ɑ=90 °, β=114.452 (3) °, γ=90 °, v=4034.3 (6) nm
3, the interfacial angle between quinoline ring and anthracene nucleus is 70.266 (120) °.
The synthesis step of monokaryon crystal of the present invention is as follows:
S1. ligand L is dissolved in DMF solution;
S2. in S1 gained solution, drip methyl alcohol, then add the DMF solution containing zinc salt, finally drip pyridine, gained mixing solutions is placed in the container of sealing, 65-85 DEG C of reaction is separated out to crystal, filters, and washing is dried;
Preferably, the mol ratio that in described S1, in ligand L and S2, zinc salt reacts is 2:1; In the present invention, described zinc salt can be known zinc salt.The formation of negative ion on monokaryon crystal of zinc salt does not affect.Described zinc salt is zinc chloride, zinc perchlorate or zinc sulfate.
Preferably, the volume ratio dripping methyl alcohol in described S1 in DMF and S2 is 1:1 ~ 2.
Should be slow during described dropping methyl alcohol, preferably, the speed dripping methyl alcohol in described S2 is 0.2 ~ 0.5ml/min.Because (E)-2-[2-(1-anthryl) vinyl]-oxine solubleness in methyl alcohol is lower, add the precipitation that methyl alcohol is conducive to crystal.
In described S2, volume of a container is 4 ~ 10:1 with the ratio of the volume of mixing solutions.
In described S2, temperature of reaction is 80 DEG C, under this temperature, can obtain the better crystal of crystal formation.The time of reaction is 24h.
Preferably, described volume of a container is 4 ~ 10:1 with the ratio of the volume of described mixing solutions.
Described (E)-2-[2-(1-anthryl) vinyl]-oxine can adopt existing method to prepare, and preferably adopts and prepares with the following method:
(1) (E)-2-[2-(1-anthryl) vinyl]-8-acetoxyl group quinoline is dissolved in pyridine;
(2) add distilled water, stir, reflux 15-17h;
(3) after reflux terminates, room temperature is cooled to, the pyridine in pressure reducing and steaming solution;
(4) add distilled water again, stirred at ambient temperature, filter and obtain solid, with solid described in distilled water wash, vacuum-drying;
The ratio of the volume of the distilled water in the volume of the pyridine in described step (1) and described step (2) is 1 ~ 3:1.
Its reaction equation is:
Described (E)-2-[9-anthryl) vinyl]-8-acetoxyl group quinoline can adopt existing method to prepare, and preferably adopts and prepares with the following method:
(1) 8-hydroxyl quinaldine red and 1-anthraldehyde are dissolved in diacetyl oxide;
(2) under the protection of nitrogen, stir, reflux 35 ~ 40h;
(3) after reflux terminates, be cooled to room temperature, be poured in frozen water, filter gained reaction solution in time having solid to separate out, gained filtrate dichloromethane extraction, obtains organic phase;
(4) by organic phase described in distilled water wash, dry removing moisture, then pressure reducing and steaming solvent, carry out separating-purifying with ethyl acetate/petroleum ether eluent.
Its reaction equation is:
Pass through fluorometric assay, we find, the ligand L adopted in the present invention and the equal Late Cambrian of title complex have aggregation-induced emission (AIE) phenomenon, ligand L and monokaryon crystal have the potential application in the fields such as chemical sensitisation, bio-sensing, biomarker, electroluminescent and logic gate device, especially, title complex luminous intensity is high, fluorescence lifetime is long, and Heat stability is good, can be used in the organic electroluminescence device being assembled into individual layer, described synthetic compound method productive rate is high, and synthesis is simple, has commercial industries prospect widely.
Compared with prior art, the invention has the beneficial effects as follows:
The present invention successfully achieves (E)-2-[2-(9-anthryl) vinyl]-oxine and Zn coordination with fluorescent effect, synthesis is containing anthracene oxine class Zn complex monokaryon crystal first, achieves the controlled synthesis containing anthracene oxine class Zn complex monokaryon crystal; Described monokaryon crystal has that luminous intensity is high, the advantage of Heat stability is good, preferably fluorescence lifetime, has significant economic worth preparing the application aspect such as luminescent material or photo-electroluminescence device.Especially, described monokaryon crystal has aggregation-induced emission (AIE) phenomenon, in the fields such as preparative chemistry sensing, bio-sensing, biomarker, electroluminescent and logic gate device, have significant economic worth.
Accompanying drawing explanation
Fig. 1 is the infrared spectrum that the present invention contains anthracene oxine class Zn complex monokaryon crystal.
Fig. 2 is the single crystal structure figure that the present invention contains anthracene oxine class Zn complex monokaryon crystal.
Fig. 3 is the solid space structure iron that the present invention contains anthracene oxine class Zn complex monokaryon crystal.
Fig. 4 is the packed structures figure that the present invention contains anthracene oxine class Zn complex monokaryon crystal.
Fig. 5 is part of the present invention (E)-2-[2-(9-anthryl) vinyl]-oxine (HL) and the Solid fluorescene spectrum containing anthracene oxine class Zn complex monokaryon crystal (Complex).
Fig. 6 is the fluorescence lifetime figure that the present invention contains anthracene oxine class Zn complex monokaryon crystal.
Fig. 7 is the thermogravimetric analysis figure that the present invention contains anthracene oxine class Zn complex monokaryon crystal.
Fig. 8 is the AIE phenomenon fluorometric titration figure that the present invention contains anthracene oxine class part.
Fig. 9 be the present invention contain anthracene oxine class Zn complex monokaryon crystal AIE phenomenon fluorometric titration figure.
Embodiment
Below in conjunction with embodiment, invention is further described.These embodiments are only describe typical case of the present invention, but the present invention is not limited thereto.Test method used in following embodiment if no special instructions, is ordinary method, the raw material used, reagent etc., and if no special instructions, being can from raw material that commercial sources obtains and the reagent such as routine is commercial.
Embodiment 1
(1) intermediate (E)-2-[9-anthryl) vinyl]-8-acetoxyl group quinoline is prepared:
A, take 8-hydroxyl quinaldine red 2.8g and 9-anthraldehyde 3g, be dissolved in the diacetyl oxide of 18ml;
B, mixed solution steps A obtained are placed in the two neck round-bottomed flasks of 50mL, carry out magnetic agitation, reflux 38h under the protection of nitrogen;
After C, heating reflux reaction terminate, be cooled to room temperature, be poured into by reaction solution in the frozen water of 800mL, filter in time having solid to separate out, filtrate, with dichloromethane extraction three times, merges three times and extracts the organic phase obtained;
D, the acetic acid washed away with distilled water in organic phase, use anhydrous sodium sulfate drying, pressure reducing and steaming solvent obtains thick product again, be that the ethyl acetate/petroleum ether of 1:10 isolates intermediate (E)-2-[2-(1-anthryl) vinyl]-8-acetoxyl group quinaldine red 4.9g as eluent by volume ratio, productive rate is 72%.
(2) part (E)-2-[2-(1-anthryl) vinyl]-oxine is prepared:
A, take (E)-2-[2-(9-anthryl) the vinyl]-8-acetoxyl group quinoline of 4.1g, and be dissolved in the reaction flask that 30mL pyridine is housed, stir 20min;
B, add in reaction flask 10mL distilled water and carry out magnetic agitation, reflux 16h;
After C, heating reflux reaction terminate, be cooled to room temperature, the pyridine in pressure reducing and steaming solution;
D, be that the ethyl acetate/petroleum ether of 1:25 isolates part (E)-2-[2-(anthryl) vinyl]-oxine 4.0g as eluent using the thick product volume ratio obtained in step C, productive rate is 92%.
(3) oxine zinc metal complexes monokaryon crystal is prepared:
A, part (E)-2-[2-(1-anthryl) the vinyl]-oxine getting 31.2mg (0.009mmol) are dissolved in the DMF solution of 1.0mL;
B, in solution, slowly drip 1.0mL methyl alcohol, the volume ratio of DMF and methyl alcohol is 1:1, and rate of addition is 0.3ml/min, drip the DMF solution that 1mL contains 1.2mg (0.0045mmol) zinc perchlorate again, finally drip 4d pyridine solution again;
C, mixing solutions is placed in the sealed sample bottle of 10mL, volume of a container is 5:1 with the ratio of the volume of mixing solutions, at 80 DEG C, react 24h;
D, have tawny bulk crystals separate out after, filter, with this crystal of ethanol repetitive scrubbing, dry, finally obtain product 4.52mg in the baking oven of 60 DEG C, productive rate is 76%.
The preparation method of embodiment 2-6 is as embodiment 1, when difference is preparation containing anthracene oxine class Zn complex monokaryon crystal, N in step A, the volume ratio (X) of the methyl alcohol dripped in dinethylformamide and step B, the ratio (Y) of volume of a container and the volume of solution, temperature of reaction (T) and reaction times (t).Parameter in each embodiment and containing the productive rate of anthracene oxine class Zn complex monokaryon crystal as table 1 and table 2.
Table 1
| X | Y | Productive rate | |
| Embodiment 2 | 1 | 10 | 80％ |
| Embodiment 3 | 0.5 | 10 | 73％ |
| Embodiment 4 | 1 | 5 | 75％ |
Table 2
| T | t | Productive rate | |
| Embodiment 5 | 65℃ | 24 | 72％ |
| Embodiment 6 | 85℃ | 24 | 80％ |
Characterization of The Products and Performance Detection:
Containing the structural confirmation of anthracene oxine class Zn complex monokaryon crystal
The product being prepared by above-described embodiment to gained carries out Fourier transform infrared spectroscopy and Advances in crystal X-ray diffraction test:
If Fig. 1 is the Fourier transform infrared spectroscopy of product, its characteristic waves (cm
-1) be 3428.17,3052.07,1602.14,1549.80,956.93,732.06.
Crystalline structure adopts German Brooker X single crystal diffractometer to measure.Brilliant X-ray diffraction data show, product belongs to oblique system, and spacer is C12/c 1 (15), Z=4,
b=9.0180 (8) nm, c=19.2691 (17) nm, ɑ=90 °, β=114.452 (3) °, γ=90 °, v=4034.3 (6) nm
3, elementary cell comprises 1 central atom Zn (II), 2 parts, 1 Pyridine Molecules.Zn (II) atom takes pentacoordinate mode, and form the octahedra geometric configuration of a distortion, the structure of its crystal as shown in figs. 2 to 4.
At room temperature carry out Solid fluorescene spectrum test to part (E)-2-[2-(9-anthryl) vinyl]-oxine with containing anthracene oxine class Zn complex monokaryon crystal, its result as shown in Figure 5.Under the rayed of 320nm, part (E)-2-[2-(9-anthryl) vinyl]-oxine and occur maximum emission peak at 517nm and 600nm respectively containing anthracene oxine class Zn complex monokaryon crystal.By comparing, can find there is good luminous intensity containing anthracene oxine class Zn complex monokaryon crystal, and there is obvious red shift in maximum emission peak.These may owing to following 2 reasons: on the one hand, and the complexing of metal ion enhances the transfer ability of electronics in skeleton and reduces the energy of transition of electron between metal and part.On the other hand, the introducing of anthryl, forms large conjugate planes, reduces the energy of system.Part and central metallic ions (Zn
2+) complexing add π
-the conjugate length of ~ π * and conjugate surface, thus reduce π in the molecular orbital(MO) of part
-energy gap between ~ π *.
At room temperature fluorometric titration experiment is carried out to part (E)-2-[2-(9-anthryl) vinyl]-oxine, its result as shown in Figure 8, poor solvent normal hexane is slowly dripped in the dichloromethane solution being dissolved with (E)-2-[2-(9-anthryl) vinyl]-oxine part, and under different normal hexane concentration, under the excitation wavelength of 340nm, do fluorometric titration experiment.By comparing, can find that part (E)-2-[2-(9-anthryl) vinyl]-oxine has good aggregation-induced emission (AIE) phenomenon.
To (E)-2-[2-(9-anthryl) vinyl]-oxine Zn complex monokaryon crystal, at room temperature carry out fluorometric titration experiment, its result as shown in Figure 9, be dissolved with the N of (E)-2-[2-(9-anthryl) vinyl]-oxine Zn complex monokaryon crystal, poor solvent ethyl acetate is slowly dripped in dinethylformamide solution, and under different ethyl acetate concentration, under the excitation wavelength of 390nm, do fluorometric titration experiment.By comparing, can find that (E)-2-[2-(9-anthryl) vinyl]-oxine Zn complex monokaryon crystal has good aggregation-induced emission (AIE) phenomenon.
As shown in Figure 6, measure further containing anthracene oxine class Zn complex monokaryon crystal fluorescence lifetime in the solid state.Experiment adopts excimer laser generation UV-light to carry out excited sample, the fluorescence that sample is inspired enters photomultiplier by a telescopic system, the signal entering signal integrator of being drawn by photomultiplier, enter the acquisition and processing that computer carries out data again, condition determination is: excitation pulse repetition rate is 10Hz, pulsewidth is 10ns, and centre wavelength is 375nm.Result shows that the fluorescence lifetime containing anthracene oxine class Zn complex monokaryon crystal is 3.73ns.
As shown in Figure 7, thermogravimetric analysis is carried out to containing anthracene oxine class Zn complex monokaryon crystal further.Condition determination is: under the protection of nitrogen; temperature rise rate is 10 DEG C/min; measuring tempeature scope is between 25 ~ 1000 DEG C; as can be seen from the figure oxine zinc metal complexes monokaryon crystal just starts to decompose gradually at about 204 DEG C and loses part, shows the Heat stability is good containing anthracene oxine class Zn complex monokaryon crystal. and this is because the rigidity condensed cyclic structure of quinoline conjugated chain thermostability and anthracene adds the stability of metal complexes.When decomposition temperature reaches 1000 DEG C, the rate of decomposition of title complex is 55%, substantially constant the rate of decomposition of 676 DEG C ~ 1000 DEG C, thus can find out that metallic compound fully decomposes.In sum, the thermal stability containing anthracene oxine class Zn complex monokaryon crystal is fine, and applicable plated film prepares corresponding luminescent device.
Obviously, the above embodiment of the present invention is only for example of the present invention is clearly described, and is not the restriction to embodiments of the present invention.For those of ordinary skill in the field, can also make other changes in different forms on the basis of the above description.Here exhaustive without the need to also giving all embodiments.All any amendments done within the spirit and principles in the present invention, equivalent to replace and improvement etc., within the protection domain that all should be included in the claims in the present invention.
Claims (10)
1. have twist structured containing an anthracene oxine class Zn complex monokaryon crystal, it is characterized in that, be that metal center and ligand L and pyridine carry out coordination and obtain with Zn, its molecular formula is ZnL
2py; Described ligand L is (E)-2-[2-(9-anthryl) vinyl]-oxine, and its molecular structure is:
py is pyridine;
The described structure containing anthracene oxine class Zn complex monokaryon crystal is as follows:
2. according to claim 1 have twist structured containing anthracene oxine class Zn complex monokaryon crystal, and it is characterized in that, the crystal parameters of described monokaryon crystal is as follows: belong to oblique system, and spacer is C12/c 1 (15), Z=4,
b=9.0180 (8) nm, c=19.2691 (17) nm, ɑ=90 °, β=114.452 (3) °, γ=90 °, v=4034.3 (6) nm
3, the interfacial angle between quinoline ring and anthracene nucleus is 70.266 (120) °.
3. according to claim 1 have a twist structured synthetic method containing anthracene oxine class Zn complex monokaryon crystal, and it is characterized in that, synthesis step is as follows:
S1. ligand L is dissolved in DMF solution;
S2. in S1 gained solution, drip methyl alcohol, then add the DMF solution containing zinc salt, finally drip pyridine, gained mixing solutions is placed in the container of sealing, 65-85 DEG C of reaction is separated out to crystal, filters, and washing is dried;
The mol ratio that in described S1, in ligand L and S2, zinc salt reacts is 2:1;
The volume ratio dripping methyl alcohol in described S1 in DMF and S2 is 1:1 ~ 2.
4. according to claim 3 have the twist structured synthetic method containing anthracene oxine class Zn complex monokaryon crystal, and it is characterized in that, the speed dripping methyl alcohol in described S2 is 0.2 ~ 0.5ml/min.
5. according to claim 3 have the twist structured synthetic method containing anthracene oxine class Zn complex monokaryon crystal, and it is characterized in that, in described S2, volume of a container is 4 ~ 10:1 with the ratio of the volume of mixing solutions.
6. according to claim 3 have the twist structured synthetic method containing anthracene oxine class Zn complex monokaryon crystal, and it is characterized in that, in described S2, temperature of reaction is 80 DEG C, and the time of reaction is 24h, and zinc salt is zinc perchlorate or zinc chloride.
7. according to claim 3 have the twist structured synthetic method containing anthracene oxine class Zn complex monokaryon crystal, and it is characterized in that, the synthetic method of described ligand L is as follows:
(1) (E)-2-[2-(9-anthryl) vinyl]-8-acetoxyl group quinoline is dissolved in pyridine;
(2) add distilled water, stir, reflux 15-17h;
(3) after reflux terminates, room temperature is cooled to, the pyridine in pressure reducing and steaming solution;
(4) add distilled water again, stirred at ambient temperature, filter and obtain solid, with solid described in distilled water wash, vacuum-drying;
The ratio of the volume of the distilled water in the volume of the pyridine in described step (1) and described step (2) is 1 ~ 3:1.
8. the synthetic method containing anthracene oxine class Zn complex monokaryon crystal according to claim 7, is characterized in that, described (E)-2-(9-anthryl) vinyl] synthetic method of-8-acetoxyl group quinoline is as follows:
(1) 8-hydroxyl quinaldine red and 9-anthraldehyde are dissolved in diacetyl oxide;
(2) under the protection of nitrogen, stir, reflux 35 ~ 40h;
(3) after reflux terminates, be cooled to room temperature, be poured in frozen water, filter gained reaction solution in time having solid to separate out, gained filtrate dichloromethane extraction, obtains organic phase;
(4) by organic phase described in distilled water wash, dry removing moisture, then pressure reducing and steaming solvent, carry out separating-purifying with ethyl acetate/petroleum ether eluent.
9. according to claim 1 have twist structuredly preparing the application in luminescent material and luminescent device containing anthracene oxine class Zn complex monokaryon crystal.
10. ligand L according to claim 1 and the application of monokaryon crystal in the fields such as chemical sensitisation, bio-sensing, biomarker, electroluminescent and logic gate device.
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