CN107188812A - 一种具有聚集诱导发光基团的二胺化合物及其制备方法和应用 - Google Patents
一种具有聚集诱导发光基团的二胺化合物及其制备方法和应用 Download PDFInfo
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- CN107188812A CN107188812A CN201710487490.6A CN201710487490A CN107188812A CN 107188812 A CN107188812 A CN 107188812A CN 201710487490 A CN201710487490 A CN 201710487490A CN 107188812 A CN107188812 A CN 107188812A
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- Prior art keywords
- aggregation
- induced emission
- diamine compound
- emission group
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- 238000002360 preparation method Methods 0.000 title claims abstract description 14
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- 238000003786 synthesis reaction Methods 0.000 claims abstract description 25
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- 229920003055 poly(ester-imide) Polymers 0.000 claims abstract description 5
- 230000002194 synthesizing effect Effects 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 125000006682 monohaloalkyl group Chemical group 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 230000002140 halogenating effect Effects 0.000 claims description 2
- 239000011630 iodine Chemical group 0.000 claims description 2
- 229910052740 iodine Chemical group 0.000 claims description 2
- 229920000642 polymer Polymers 0.000 abstract description 10
- 238000006069 Suzuki reaction reaction Methods 0.000 abstract description 7
- 150000004985 diamines Chemical class 0.000 abstract description 6
- 238000005166 mechanoluminescence Methods 0.000 abstract description 4
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- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 238000010189 synthetic method Methods 0.000 abstract description 2
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- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
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- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene chloride Substances ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 17
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- 229920005575 poly(amic acid) Polymers 0.000 description 5
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- RICKKZXCGCSLIU-UHFFFAOYSA-N 2-[2-[carboxymethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]ethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]acetic acid Chemical compound CC1=NC=C(CO)C(CN(CCN(CC(O)=O)CC=2C(=C(C)N=CC=2CO)O)CC(O)=O)=C1O RICKKZXCGCSLIU-UHFFFAOYSA-N 0.000 description 4
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L magnesium sulphate Substances [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
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- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
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- NXXDSCQBUHFJLF-UHFFFAOYSA-N C1=CC=C(C=C1)C(=C(C2=CC=CC=C2)C3=CC(=CC(=C3)C4=CC=C(C=C4)N)C5=CC=C(C=C5)N)C6=CC=CC=C6 Chemical compound C1=CC=C(C=C1)C(=C(C2=CC=CC=C2)C3=CC(=CC(=C3)C4=CC=C(C=C4)N)C5=CC=C(C=C5)N)C6=CC=CC=C6 NXXDSCQBUHFJLF-UHFFFAOYSA-N 0.000 description 2
- NMQMULZKTWRGIM-UHFFFAOYSA-N Cl.B(O)(O)O.NC1=CC=CC=C1 Chemical class Cl.B(O)(O)O.NC1=CC=CC=C1 NMQMULZKTWRGIM-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- XEVAJAYAWGOWJW-UHFFFAOYSA-N NC1=CC=CC(C2=CC(C(C3=CC=CC=C3)=C(C3=CC=CC=C3)C3=CC=CC=C3)=CC(C3=CC(N)=CC=C3)=C2)=C1 Chemical compound NC1=CC=CC(C2=CC(C(C3=CC=CC=C3)=C(C3=CC=CC=C3)C3=CC=CC=C3)=CC(C3=CC(N)=CC=C3)=C2)=C1 XEVAJAYAWGOWJW-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
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- VUQVJIUBUPPCDB-UHFFFAOYSA-N (1-bromo-2,2-diphenylethenyl)benzene Chemical compound C=1C=CC=CC=1C(Br)=C(C=1C=CC=CC=1)C1=CC=CC=C1 VUQVJIUBUPPCDB-UHFFFAOYSA-N 0.000 description 1
- UTHULKKJYXJZLV-UHFFFAOYSA-N (3-aminophenoxy)boronic acid Chemical compound NC1=CC=CC(OB(O)O)=C1 UTHULKKJYXJZLV-UHFFFAOYSA-N 0.000 description 1
- AMZCTIQOIRPISZ-UHFFFAOYSA-N 2,6-dibromo-4-(1,2,2-triphenylethenyl)aniline Chemical compound BrC1=C(N)C(=CC(=C1)C(=C(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1)Br AMZCTIQOIRPISZ-UHFFFAOYSA-N 0.000 description 1
- WCNQRPKNQRXHQJ-UHFFFAOYSA-N 4-(1,2,2-triphenylethenyl)aniline Chemical compound C1=CC(N)=CC=C1C(C=1C=CC=CC=1)=C(C=1C=CC=CC=1)C1=CC=CC=C1 WCNQRPKNQRXHQJ-UHFFFAOYSA-N 0.000 description 1
- VXYUEGCZVQJNIR-UHFFFAOYSA-N BrC=1C=C(C=C(C=1)Br)C(=C(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound BrC=1C=C(C=C(C=1)Br)C(=C(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1 VXYUEGCZVQJNIR-UHFFFAOYSA-N 0.000 description 1
- 238000006546 Horner-Wadsworth-Emmons reaction Methods 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- QPFGXFOAVMQQBS-UHFFFAOYSA-N NC(C=C1)=CC=C1C1=CC(C(C=C2)=CC=C2N)=CC(C(C2=CC=CC=C2)=C(C(C=C2)=CC=C2C2=CC=CC=C2)C(C=C2)=CC=C2C2=CC=CC=C2)=C1 Chemical compound NC(C=C1)=CC=C1C1=CC(C(C=C2)=CC=C2N)=CC(C(C2=CC=CC=C2)=C(C(C=C2)=CC=C2C2=CC=CC=C2)C(C=C2)=CC=C2C2=CC=CC=C2)=C1 QPFGXFOAVMQQBS-UHFFFAOYSA-N 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
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- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000003486 chemical etching Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
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- 230000008025 crystallization Effects 0.000 description 1
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- 230000000694 effects Effects 0.000 description 1
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- 125000000524 functional group Chemical group 0.000 description 1
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- JGJLWPGRMCADHB-UHFFFAOYSA-N hypobromite Inorganic materials Br[O-] JGJLWPGRMCADHB-UHFFFAOYSA-N 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- CKJNUZNMWOVDFN-UHFFFAOYSA-N methanone Chemical compound O=[CH-] CKJNUZNMWOVDFN-UHFFFAOYSA-N 0.000 description 1
- 238000004377 microelectronic Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- OJBSYCMUWONLAE-UHFFFAOYSA-N n,n,4-triphenylaniline Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 OJBSYCMUWONLAE-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
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- 239000003880 polar aprotic solvent Substances 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 230000008569 process Effects 0.000 description 1
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- 238000010926 purge Methods 0.000 description 1
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- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
- C07C211/49—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton
- C07C211/50—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton with at least two amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B42D25/36—Identification or security features, e.g. for preventing forgery comprising special materials
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1003—Preparatory processes
- C08G73/1007—Preparatory processes from tetracarboxylic acids or derivatives and diamines
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1067—Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1075—Partially aromatic polyimides
- C08G73/1078—Partially aromatic polyimides wholly aromatic in the diamino moiety
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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- C09K2211/10—Non-macromolecular compounds
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- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- C09K2211/1408—Carbocyclic compounds
- C09K2211/1425—Non-condensed systems
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/14—Macromolecular compounds
- C09K2211/1441—Heterocyclic
- C09K2211/1466—Heterocyclic containing nitrogen as the only heteroatom
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- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
本发明公开了一种具有聚集诱导发光基团的二胺及其制备方法和应用。本发明的具有聚集诱导发光基团的二胺化合物，制备方法为：首先通过Suzuki反应，制备得到基于多苯乙烯结构的含卤中间体，再通过卤代、重氮化脱氨基、Suzuki反应等多步反应得到基于多苯乙烯结构的新型二胺化合物。本发明的合成方法工艺简单多样，纯化容易，合适工业化生产；合成的二胺化合物具有典型的聚集诱导发光性能、高的发光效率和力致发光变色性能，可用于合成聚酰胺、聚酰亚胺、聚酰胺酰亚胺、聚酯酰亚胺等高性能、功能化聚合物，或用于电致发光器件中发光层材料和防伪器件。
Description
技术领域
本发明涉及材料科学领域，特别是一类具有聚集诱导发光基团的二胺及其制备方法和应用。
技术背景
聚酰亚胺是主链上含有酰亚胺环的一类高性能聚合物，具有高力学强度、耐高低温、耐化学腐蚀、良好的尺寸稳定性和介电性能等优点，在航天航空、微电子器件、液晶显示等领域具有广泛的应用。另一方面，随着显示技术的进步，有机发光二极管(OrganicLight-Emitting Diode，OLED)以其主动发光、全彩色显示、低功耗、低启动电压、高亮度、快速响应、宽视角、加工工艺简单及低成本等优点，成为近十年来有机光电领域的研究热点之一。相对于有机小分子发光材料，聚合物发光材料可通过旋涂、喷墨打印、浸渍等多种低成本技术大面积成膜，做成结构简单的柔性器件，并且发光聚合物一般具有大共轭的电子结构，可通过分子结构设计对其发光颜色进行调节。因此，在未来的柔性可印刷显示领域，基于聚合物发光材料的有机发光二极管(Polymer Light-Emitting Diode，PLED)将成为研究的重点。但是，聚合物发光材料的制备、纯化过程复杂，彩色化难且寿命短，这些都成为制约其在PLED领域应用的瓶颈。特别是PLED器件的制作过程中，这些有机材料会出现氧化和光降解等化学变化，同时由于其高温下尺寸不稳定及其易结晶等性质，严重影响器件的稳定性和寿命。因此，具有优异热稳定性能的聚酰亚胺材料可克服普通有机材料的上述缺点，从而成为下一代PLED发光材料的优秀候选对象。
聚酰亚胺一般由二胺和二酐单体在极性非质子性溶剂中先形成聚酰胺酸前驱体，然后通过脱水酰亚胺化反应制备得到。为获得高效率发光的聚酰亚胺，一般采用在结构可设计性优异的二胺单体上引入不同的功能性基团，赋予聚酰亚胺独特的光电性能。目前，具有一定光致发光效率的聚酰亚胺，一般采用在二胺或二酐单体中引入有机共轭发色基团。如US 5677417、JP 2008297354、CN1371932和JP 2005320393等。但这类聚酰亚胺中的发色基团平面化程度高，基团堆叠严重；主链间、侧基间或主链与侧基间还存在较强的相互作用，电荷转移络合物的数量得不到减少，电荷转移效应仍较强。因此，有必要在二胺单体的合成设计上进一步深入研究。
发明内容
本发明的目的是提供一种具有聚集诱导发光基团的二胺化合物，该类化合物具有典型的聚集诱导发光性能、力致发光变色特性、高的发光效率、良好的热稳定性和溶解性能。
本发明的另一个目的在于提供上述具有聚集诱导发光基团的二胺化合物的制备方法。
本发明还有一个目的是提供上述具有聚集诱导发光基团的二胺化合物的应用，其既可用于合成新型聚酰胺、聚酰亚胺、聚酰胺酰亚胺、聚酯酰亚胺等高性能、功能化聚合物，也可用于光电材料和防伪材料的制备。
本发明是这样实现的：一种具有聚集诱导发光基团的二胺化合物，该化合物的结构通式如下所示：
其中，Ar1、Ar2和Ar3相同或不同，分别选自下列结构式中的一种：
上述通式所示的具有聚集诱导发光基团的二胺化合物的制备方法，包括以下步骤：(1) 单卤代多苯乙烯的合成；(2)将步骤(1)中的单卤代多苯乙烯通过Suzuki反应，制备得到含有多苯乙烯结构的含胺中间体；(3)将步骤(2)中的含胺中间体通过卤代反应，合成得到含氨基的二卤代化合物；(4)将步骤(3)中含氨基的二卤代化合物进行重氮化脱氨基反应，合成得到二卤化合物；(5)将步骤(4)中的二卤化合物通过Suzuki反应制备得到如通式所示结构的具有聚集诱导发光基团的二胺化合物。
本发明的一类具有聚集诱导发光基团的二胺化合物,合成方法工艺简单，纯化容易，合适工业化生产；合成的二胺化合物热稳定性高，具有典型的聚集诱导发光特性、力致发光变色特性、高的发光效率和溶解性能。其既可用于合成新型聚酰胺、聚酰亚胺、聚酰胺酰亚胺、聚酯酰亚胺等高性能、功能化聚合物，也可用于光电材料的制备。
具体实施方式
本发明是一类具有聚集诱导发光基团的二胺化合物，该类化合物的结构通式如下：
其中，Ar1、Ar2和Ar3相同或不同，分别选自下列结构式中的一种：
对于上述通式所示的一类具有聚集诱导发光基团的二胺化合物的制备方法，包括以下步骤：(1)单卤代多苯乙烯的合成；(2)将步骤(1)中的单卤代多苯乙烯通过Suzuki反应，制备得到含有多苯乙烯结构的含胺中间体；(3)将步骤(2)中的含胺中间体通过卤代反应，合成得到含氨基的二卤代化合物；(4)将步骤(3)中含氨基的二卤代化合物进行重氮化脱氨基反应，合成得到二卤化合物；(5)将步骤(4)中的二卤化合物通过Suzuki反应制备得到如式(I)所示结构的具有聚集诱导发光基团的二胺化合物。
其中，单卤代多苯乙烯的结构式为：
其中X为氯、溴或碘；该化合物可简单地通过Wittig-Horner反应或多苯乙烯的溴代反应制备得到。
Ar1、Ar2和Ar3相同或不同，分别选自下列结构式中的一种：
所制得的具有聚集诱导发光基团的二胺化合物，既可用于合成新型聚酰胺、聚酰亚胺、聚酰胺酰亚胺、聚酯酰亚胺等高性能、功能化聚合物，也可用于光电材料的制备。
下面给出实例以对本发明作更详细的说明，有必要指出的是以下实施例不能解释为对发明保护范围的限制。该领域的技术熟练人员根据上述发明内容对本发明作出的一些非本质的改进和调整，仍应属于本发明的保护范围。
实施例1
5'-(1,2,2-triphenylvinyl)-[1,1':3',1”-terphenyl]-4,4”-diamine的合成
(1)中间体4-(1,2,2-triphenylvinyl)aniline(TPENH2)的合成：
于500mL三颈烧瓶中加入(2-bromoethene-1,1,2-triyl)tribenzene(5.03g，15mmol) 和4-氨基苯硼酸盐酸盐(2.86g，17mmol)，加入100mL四氢呋喃，搅拌至形成均一澄清溶液。加入90mL K2CO3溶液(2M)，Ar气保护下升温至80℃，加入0.02g Pd(PPh3)4，搅拌回流反应24h。冷却至室温，分离取有机相，水相用CH2Cl2萃取两遍，合并有机相，加入无水MgSO4干燥。抽滤取滤液，减压旋干溶剂，以CH2Cl2/正己烷为洗脱剂进行柱层析，收集产物层，减压旋干溶剂，真空干燥，得浅黄色粉末4.77g，产率92％。该中间体结构如下：
(2)中间体2,6-dibromo-4-(1,2,2-triphenylvinyl)aniline(TPENH2Br)的合成：
于250mL单颈烧瓶中加入TPENH2(3.47g，10mmol)和65mL N,N-二甲基甲酰胺，搅拌至溶解，在冰浴下滴加含N-溴代丁二酰亚胺(3.92g，22mmol)的20mL N,N-二甲基甲酰胺溶液。滴加完后继续反应3h。倒入水中析出沉淀，抽滤取滤渣，以CH2Cl2/正己烷为洗脱剂进行柱层析，收集产物层，减压旋干溶剂，真空干燥，得浅黄色粉末3.36g，产率66％。该中间体结构如下：
(3)中间体(2-(3,5-dibromophenyl)ethene-1,1,2-triyl)tribenzene(TPEBr)的合成：
于500mL圆底烧瓶中加入TPENH2Br(5.05g，10mmol)和150mL无水甲醇，缓慢加入2.25mL浓硫酸。分批加入NaNO2(2.49g，36mmol)，Ar气保护下升温至80℃，搅拌反应6h。旋转蒸发除去乙醇，加入20mL水，用CH2Cl2萃取(50mL×3)，取有机相，利用 CH2Cl2/正己烷为洗脱剂进行柱层析，收集产物层，减压旋干溶剂，真空干燥，得白色粉末3.73 g，产率76％。该中间体结构如下：
(4)5'-(1,2,2-triphenylvinyl)-[1,1':3',1”-terphenyl]-4,4”-diamine的合成：
于500mL三颈烧瓶中加入TPEBr(7.35g，15mmol)和4-氨基苯硼酸盐酸盐(2.86g，17mmol)，加入100mL四氢呋喃，搅拌至形成均一澄清溶液。加入90mL K2CO3溶液(2M)， Ar气保护下升温至80℃，加入0.02g Pd(PPh3)4，搅拌回流反应24h。冷却至室温，分离取有机相，水相用CH2Cl2萃取两遍，合并有机相，加入无水MgSO4干燥。抽滤取滤液，减压旋干溶剂，以CH2Cl2/正己烷为洗脱剂进行柱层析，收集产物层，减压旋干溶剂，真空干燥，得浅黄色粉末6.87g，产率89％。该化合物具有典型的聚集诱导发光和力致发光变色性质，其熔点为275℃，5％热分解温度为384℃。其荧光最强峰对应的波长为451nm。化合物的红外光谱图3450～3330cm-1范围出现氨基-NH2的特征吸收峰。
(5)应用于合成聚酰亚胺膜：
将5'-(1,2,2-triphenylvinyl)-[1,1':3',1”-terphenyl]-4,4”-diamine与氢化均苯四酸二酐反应，获得聚酰胺酸溶液。将所得的聚酰胺酸溶液进行热酰亚胺化，冷却后可得到聚酰亚胺膜。该聚酰亚胺膜具有聚集诱导发光性能，厚度约为35μm的薄膜的绝对荧光量子产率为38％，其荧光最强峰对应的波长为482nm，5％的热失重温度为530℃，玻璃化转变温度为398℃。分子结构式如下：
实施例2
5'-(1,2,2-triphenylvinyl)-[1,1':3',1”-terphenyl]-3,3”-diamine的合成
根据实施例1中的步骤1-3合成得中间体TPEBr。于500mL三颈烧瓶中加入TPEBr(7.35 g，15mmol)和3-氨基苯硼酸(2.33g，17mmol)，加入100mL四氢呋喃，搅拌至形成均一澄清溶液。加入90mL K2CO3溶液(2M)，Ar气保护下升温至80℃，加入0.02g Pd(PPh3)4，搅拌回流反应24h。冷却至室温，分离取有机相，水相用CH2Cl2萃取两遍，合并有机相，加入无水MgSO4干燥。抽滤取滤液，减压旋干溶剂，以CH2Cl2/正己烷为洗脱剂进行柱层析，收集产物层，减压旋干溶剂，真空干燥，得浅黄色粉末6.41g，产率83％。该化合物具有典型的聚集诱导发光和力致发光变色性质，其熔点为211℃，5％热分解温度为402℃。其荧光最强峰对应的波长为415nm。化合物的红外光谱图3450～3330cm-1范围出现氨基-NH2的特征吸收峰。
应用于合成聚酰亚胺膜：
室温下，将5'-(1,2,2-triphenylvinyl)-[1,1':3',1”-terphenyl]-3,3”-diamine 与4,4'-六氟异丙基邻苯二甲酸酐反应，获得聚酰胺酸溶液。将聚酰胺酸溶液进行化学酰亚胺化，得到聚酰亚胺膜。该聚酰亚胺膜具有聚集诱导发光性能，其荧光最强峰对应的波长为 533nm，5％的热失重温度为569℃，玻璃化转变温度为286℃。分子结构式如下：
实施例3
5'-(2,2-di([1,1'-biphenyl]-4-yl)-1-phenylvinyl)-[1,1':3',1”-terphenyl]-4,4 ”-diamine的合成
(1)4,4”-(2-bromo-2-phenylethene-1,1-diyl)di-1,1'-biphenyl(TPEPhBr)的合成：
于500mL圆底烧瓶中加入4,4”-(2-phenylethene-1,1-diyl)di-1,1'-biphenyl(1.7 g，4.2mmol)和20mL四氯化碳。于0℃滴加溴素(0.23mL，4.6mmol)，继续搅拌反应 2h。向反应液中加入5mL三乙胺，用乙酸乙酯(10mL×3)萃取，有机层用卤水洗涤、无水硫酸镁干燥，用乙酸乙酯/正己烷为洗脱剂进行柱层析，收集产物层，减压旋干溶剂，真空干燥，得产物。
(2)5'-(2,2-di([1,1'-biphenyl]-4-yl)-1-phenylvinyl)-[1,1':3',1”-terphenyl] -4,4”-diamine(TPEPhNH2)的合成：
根据实施例1中的步骤1-4，对上步产物TPEPhBr依次进行Suzuki反应、溴代反应、重氮化去氨基反应和Suzuki反应，制备得到TPEPhNH2。
实施例4
5'-(1-([1,1'-biphenyl]-4-yl)-2,2-bis(4'-(diphenylamino)-[1,1'-biphenyl]-4-y l)vinyl)-[1,1':3',1”-terphenyl]-4,4”-diamine的合成
(1)bis(4'-(diphenylamino)-[1,1'-biphenyl]-4-yl)methanone(triPhN-one)的合成：
将4,4'-二溴二苯酮(3.4g，10mmol)和4-苯硼酸三苯胺(5.78g，20mmol)溶解在250mL四氢呋喃中，加入2M碳酸钾的水溶液(65mL)，搅拌下通氩气30min后，加入催化量的Pd(PPh3)4，加热至75℃反应24h。减压旋蒸除去溶剂，粗产物用二氯甲烷/正己烷为洗脱剂进行柱层析，收集产物层，减压旋干溶剂，真空干燥，得产物。
(2)4',4”'-(2-([1,1'-biphenyl]-4-yl)ethene-1,1-diyl)bis(N,N-diphenyl-[1,1'-biphenyl]-4-amine)(triPhN-TPE)的合成
把triPhN-one(5.8g，10mmol)和联苯亚甲基膦酸二乙酯(3.9g，12.9mmol)溶解于40mL四氢呋喃中，加入叔丁醇钾(1.44g，12.9mmol)，在氩气保护下常温搅拌反应4h。减压除去溶剂。粗产品以正己烷为洗脱剂进行柱层析，收集产物层，减压旋干溶剂，真空干燥，得产物。
(3)5'-(1-([1,1'-biphenyl]-4-yl)-2,2-bis(4'-(diphenylamino)-[1,1'-biphenyl] -4-yl)vinyl)-[1,1':3',1”-terphenyl]-4,4”-diamine(triPhN-NH2)的合成
根据实施例3中的步骤1和1中的步骤1-4，对上步产物TPEPhBr依次进行溴水溴代反应、Suzuki反应、NBS溴代反应、重氮化去氨基反应和Suzuki反应，制备得到标题triPhN-NH2。
Claims (5)
1.一种具有聚集诱导发光基团的二胺化合物，其分子结构通式为：
其中，Ar1、Ar2和Ar3相同或不同，分别选自下列结构式中的一种：
2.权利要求1所述具有聚集诱导发光基团的二胺化合物的制备方法，其特征在于包括以下步骤：
(1)单卤代多苯乙烯的合成；
(2)将步骤(1)中的单卤代多苯乙烯通过Suzuki反应，制备得到含有多苯乙烯结构的含胺中间体；
(3)将步骤(2)中的含胺中间体通过卤代反应，合成得到含氨基的二卤代化合物；
(4)将步骤(3)中含氨基的二卤代化合物进行重氮化脱氨基反应，合成得到二卤化合物；
(5)将步骤(4)中的二卤化合物通过Suzuki反应制备得到权利要求1通式所示结构的具有聚集诱导发光基团的二胺化合物。
3.根据权利要求2所述的具有聚集诱导发光基团的二胺化合物的制备方法，其特征在于：所述的步骤(1)中的单卤代多苯乙烯的结构式为：
其中X为氯、溴或碘；
Ar1、Ar2和Ar3相同或不同，分别选自下列结构式中的一种：
4.权利要求1所述具有聚集诱导发光基团的二胺化合物在合成新型聚酰胺、聚酰亚胺、聚酰胺酰亚胺、聚酯酰亚胺上的应用。
5.权利要求1所述具有聚集诱导发光基团的二胺化合物在制备光电材料、防伪材料上的应用。
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| CN110606810A (zh) * | 2019-10-08 | 2019-12-24 | 吉林大学 | 含四苯基乙烯-双芳胺结构的二胺单体、制备方法及其在聚酰胺合成中的应用 |
| CN114481678A (zh) * | 2022-01-04 | 2022-05-13 | 煤炭科学研究总院有限公司 | 一种改性对位芳纶纳米纤维及其制备方法和应用 |
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| CN104341311A (zh) * | 2013-07-31 | 2015-02-11 | 中山大学 | 新型二胺化合物及其制备方法和应用 |
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| CN104341311A (zh) * | 2013-07-31 | 2015-02-11 | 中山大学 | 新型二胺化合物及其制备方法和应用 |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110606810A (zh) * | 2019-10-08 | 2019-12-24 | 吉林大学 | 含四苯基乙烯-双芳胺结构的二胺单体、制备方法及其在聚酰胺合成中的应用 |
| CN110606810B (zh) * | 2019-10-08 | 2021-03-30 | 吉林大学 | 含四苯基乙烯-双芳胺结构的二胺单体、制备方法及其在聚酰胺合成中的应用 |
| CN114481678A (zh) * | 2022-01-04 | 2022-05-13 | 煤炭科学研究总院有限公司 | 一种改性对位芳纶纳米纤维及其制备方法和应用 |
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