CN114933595B - 一种2-苯基苯并噁唑多刺激响应荧光材料及其制备方法 - Google Patents
一种2-苯基苯并噁唑多刺激响应荧光材料及其制备方法 Download PDFInfo
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- 239000000463 material Substances 0.000 title claims abstract description 37
- 230000004044 response Effects 0.000 title claims abstract description 28
- FIISKTXZUZBTRC-UHFFFAOYSA-N 2-phenyl-1,3-benzoxazole Chemical compound C1=CC=CC=C1C1=NC2=CC=CC=C2O1 FIISKTXZUZBTRC-UHFFFAOYSA-N 0.000 title claims abstract description 14
- 238000002360 preparation method Methods 0.000 title abstract description 9
- 238000006243 chemical reaction Methods 0.000 claims description 54
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 40
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 38
- 239000012043 crude product Substances 0.000 claims description 38
- 239000000843 powder Substances 0.000 claims description 38
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 23
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- 239000003208 petroleum Substances 0.000 claims description 19
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 19
- 238000010438 heat treatment Methods 0.000 claims description 15
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 14
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 14
- 239000003480 eluent Substances 0.000 claims description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 12
- 238000001914 filtration Methods 0.000 claims description 12
- 239000001301 oxygen Substances 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 238000002390 rotary evaporation Methods 0.000 claims description 12
- 238000010898 silica gel chromatography Methods 0.000 claims description 10
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 claims description 10
- 238000004440 column chromatography Methods 0.000 claims description 9
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- 239000012074 organic phase Substances 0.000 claims description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 7
- 238000001816 cooling Methods 0.000 claims description 7
- 238000000605 extraction Methods 0.000 claims description 7
- 239000000706 filtrate Substances 0.000 claims description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 7
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 7
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims description 6
- -1 2-phenylbenzoxazolyl Chemical group 0.000 claims description 6
- 229950000688 phenothiazine Drugs 0.000 claims description 6
- UOQXIWFBQSVDPP-UHFFFAOYSA-N 4-fluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1 UOQXIWFBQSVDPP-UHFFFAOYSA-N 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 229910000160 potassium phosphate Inorganic materials 0.000 claims description 5
- 235000011009 potassium phosphates Nutrition 0.000 claims description 5
- RBVHJNZMSBQFDK-UHFFFAOYSA-N 2-(4-bromophenyl)-1,3-benzoxazole Chemical compound C1=CC(Br)=CC=C1C1=NC2=CC=CC=C2O1 RBVHJNZMSBQFDK-UHFFFAOYSA-N 0.000 claims description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 4
- BKRKYEFQSANYGA-UHFFFAOYSA-N bromo-methyl-triphenyl-$l^{5}-phosphane Chemical compound C=1C=CC=CC=1P(Br)(C=1C=CC=CC=1)(C)C1=CC=CC=C1 BKRKYEFQSANYGA-UHFFFAOYSA-N 0.000 claims 1
- 238000005086 pumping Methods 0.000 claims 1
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- 239000002253 acid Substances 0.000 abstract description 10
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- 125000001424 substituent group Chemical group 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 description 53
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 21
- 239000013078 crystal Substances 0.000 description 13
- 238000004020 luminiscence type Methods 0.000 description 12
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- LSEFCHWGJNHZNT-UHFFFAOYSA-M methyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 LSEFCHWGJNHZNT-UHFFFAOYSA-M 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 238000005859 coupling reaction Methods 0.000 description 5
- 230000003287 optical effect Effects 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- WPDAVTSOEQEGMS-UHFFFAOYSA-N 9,10-dihydroanthracene Chemical compound C1=CC=C2CC3=CC=CC=C3CC2=C1 WPDAVTSOEQEGMS-UHFFFAOYSA-N 0.000 description 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 230000000638 stimulation Effects 0.000 description 4
- VNANLRAWGZHALH-UHFFFAOYSA-N 2h-oxazine;phenol Chemical group N1OC=CC=C1.OC1=CC=CC=C1 VNANLRAWGZHALH-UHFFFAOYSA-N 0.000 description 3
- WOTNVYMPQOWYSY-UHFFFAOYSA-N 5-bromo-2-phenyl-1,3-benzoxazole Chemical compound N=1C2=CC(Br)=CC=C2OC=1C1=CC=CC=C1 WOTNVYMPQOWYSY-UHFFFAOYSA-N 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 230000001678 irradiating effect Effects 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 230000002441 reversible effect Effects 0.000 description 3
- PHKYYUQQYARDIU-UHFFFAOYSA-N 3-methyl-9h-carbazole Chemical compound C1=CC=C2C3=CC(C)=CC=C3NC2=C1 PHKYYUQQYARDIU-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000005452 bending Methods 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000006617 triphenylamine group Chemical group 0.000 description 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 1
- GJFNNZBYCMUAHY-ZHACJKMWSA-N 2-[(e)-2-phenylethenyl]-1,3-benzoxazole Chemical class N=1C2=CC=CC=C2OC=1/C=C/C1=CC=CC=C1 GJFNNZBYCMUAHY-ZHACJKMWSA-N 0.000 description 1
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
- CTRXZOLNEVJBDX-UHFFFAOYSA-N 4-(4-methoxy-n-(4-methoxyphenyl)anilino)benzaldehyde Chemical compound C1=CC(OC)=CC=C1N(C=1C=CC(C=O)=CC=1)C1=CC=C(OC)C=C1 CTRXZOLNEVJBDX-UHFFFAOYSA-N 0.000 description 1
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical group C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 229910052743 krypton Inorganic materials 0.000 description 1
- DNNSSWSSYDEUBZ-UHFFFAOYSA-N krypton atom Chemical compound [Kr] DNNSSWSSYDEUBZ-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052754 neon Inorganic materials 0.000 description 1
- GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000002265 redox agent Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D263/57—Aryl or substituted aryl radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings
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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
- 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
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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
- 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
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- 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
- C09K2211/10—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
- C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
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- Chemical & Material Sciences (AREA)
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- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
本发明提供一种2‑苯基苯并噁唑多刺激响应荧光材料及其制备方法,属于荧光材料技术领域。该荧光材料以2‑苯基苯并噁唑作为分子骨架,并修饰有庞大的共轭结构取代基团,该多重刺激响应变色材料结构简单,对比度高,荧光量子产率高。经实验测试,该多重刺激响应变色材料可对研磨、酸熏蒸和温度等外界刺激产生相应的响应信号,使得发光强度或发光颜色发生明显改变,具有明显的力致变色、酸致变色以及热致变色性质,刺激先后会可逆复原为初始的颜色及状态。同时还具有柔性和光波导性质,满足了当前多元化的应用需求,并可广泛应用于有机激光、检测、传感、照明、显示和信息储存等多个领域。
Description
技术领域
本发明属于荧光材料技术领域,具体涉及一种2-苯基苯并噁唑多刺激响应荧光材料及其制备方法。
背景技术
刺激响应型材料是可感知和回应环境变化的智能材料,因其新颖的功能与广泛的应用前景而受到研究者们的青睐。具有对外界刺激,如物理刺激(温度、光、超声波、电压、压力)。化学刺激(pH、氧化还原剂和其它特定分子如CO2)等等。近年来,许多新型智能荧光材料被开发出来,并广泛应用于传感器、荧光探针、发光材料和光电显示器件等方面。然而,许多刺激响应材料都是功能单一并且在固体状态或者晶体时,发光减弱还具有脆性,这也极大地限制了该些发光材料的应用。2-苯基苯并噁唑(PBO)是荧光有机染料的重要基本单元。特别吸引人的是其高量子产率、易于合成以及优异的热、化学和光化学稳定性,使得PBO衍生物广泛用于溶液和聚合物中。作为刺激响应材料,其价值也已被Fery-Forgue(Bremond,E.;Leygue,N.;Jaouhari,T.;Saffon-Merceron,N.;Erriguible,A.;Fery-Forgues,S.,Effect ofsubstitution on the solid-state fluorescence properties ofstyrylbenzoxazole derivatives with terminal dicyanomethylene group.JournalofPhotochemistry and PhotobiologyA:Chemistry 2021,404.)和薛(Xue,P.;Yao,B.;Sun,J.;Xu,Q.;Chen,P.;Zhang,Z.;Lu,R.,Phenothiazine-based benzoxazole derivatesexhibiting mechanochromic luminescence:the effect of abromineatom.J.Mater.Chem.C 2014,2(20),3942-3950.)等人确立。但这一类衍生物刺激响应邻域的研究还是单一刺激较多而且还没有出现过三个及以上多刺激响应并兼具多元化的功能于一身的材料。
发明内容
本发明的目光是为了解决现有的变色材料功能单一,且在晶体状态下具有脆性的问题,而提供一种2-苯基苯并噁唑多刺激响应荧光材料及其制备方法。
本发明首先提供一种2-苯基苯并噁唑多刺激响应荧光材料,结构式如式1或2所示:
其中R1选自吲哚、咔唑、9,10-二氢蒽、酚噻嗪、或酚噁嗪类基团;R2选自咔唑、9,10-二氢蒽、酚噻嗪、酚噁嗪或三苯胺类基团。
优选的是,所述的R1中吲哚类基团如下:
所述的R1中酚噁嗪类基团如下:
所述的R1中的酚噻嗪类基团如下:
所述的R1中的咔唑类基团如下:
所述的R1中的9,10-二氢蒽类基团如下:
优选的是,所述的R2中三苯胺类基团如下:
所述的R2中酚噁嗪类基团如下:
所述的R2中酚噻嗪类基团如下:
所述的R2中咔唑类基团如下:
所述的R2中9,10-二氢蒽类基团如下:
优选的是,所述的2-苯基苯并噁唑多刺激响应荧光材料,结构式如下:
本发明还提供一种2-苯基苯并噁唑多刺激响应荧光材料的制备方法,包括:
将式a所示的化合物和含有R1的化合物进行Heck偶联反应,得到式1所示的2-苯基苯并噁唑多刺激响应荧光材料;
或者将式b所示的化合物和含有R2的化合物进行Heck偶联反应,得到式2所示的2-苯基苯并噁唑多刺激响应荧光材料:
式a所示的化合物和式b所示的化合物中,X选为卤素。
优选的是,所述的Heck偶联反应的反应温度为100-110℃,反应时间为12-24h。
优选的是,所述的式a所示的化合物和含有R1的化合物的摩尔比为1:(1.1-2);
式b所示的化合物和含有R2的化合物的摩尔比为1:(1.1-2)。
优选的是,所述的Heck偶联反应过程中加入钯配合物、碱和溶剂。
优选的是,所述的钯配合物为醋酸钯,碱为无水K2CO3,溶剂为甲苯。
本发明的有益效果
本发明一种2-苯基苯并噁唑多刺激响应荧光材料及其制备方法,该荧光材料以2-苯基苯并噁唑作为分子骨架,并修饰有庞大的共轭结构取代基团,该多重刺激响应变色材料结构简单,对比度高,荧光量子产率高。经实验测试,该多重刺激响应变色材料可对研磨、酸熏蒸和温度等外界刺激产生相应的响应信号,使得发光强度或发光颜色发生明显改变,具有明显的力致变色、酸致变色以及热致变色性质,刺激先后会可逆复原为初始的颜色及状态。同时还具有光波导性质,满足了当前多元化的应用需求,并可广泛应用于有机激光、检测、传感、照明、显示和信息储存等多个领域。上述多重刺激响应变色材料集多重刺激响应变色,光波导性质及柔性于一体,将该多重刺激相应变色材料应用于有机激光,压力传感器和检测中对比度高,敏感度高有利于极大地拓宽刺激响应材料的应用场景。
本发明的合成路线简单,产率高,反应条件可控,易于实现多重刺激响应变色材料的规模化制备。
附图说明
图1是实施例1制备的化合物在固态下的日光下发光情况。
图2是实施例1制备的化合物在固态下365nm紫外灯照射下的发光情况
图3是实施例1的化合物粉末经研磨后365nm紫外灯下的照射情况。
图4是实施例1的化合物粉末经三氟乙酸后365nm紫外灯下的照射情况。
图5是实施例1的化合物粉末经加热后365nm紫外灯下的照射情况。
图6是实施例1的化合物单晶在365nm紫外灯照射下的情况。
图7是实施例1的化合物单晶弯曲状态下的情况。
图8是实施例1的化合物在DMSO中核磁共振图谱(400MHZ)。
具体实施方式
为了使本申请要解决的技术问题、技术方案及有益效果更加清楚明白,以下结合实施例,对本申请进行进一步详细说明。应当理解,此处所描述的具体实施例仅仅用以解释本申请,并不用于限定本申请。
本发明所述的一种2-苯基苯并噁唑多刺激响应荧光材料的制备方法中进行Heck偶联反应的步骤可参考本领域的常规方法,例如混合体系中加入例如醋酸钯(0.1-0.25eq)等钯配合物、碱和溶剂,然后在惰性气体保护下进行回流反应。其中,惰性气体包括但不限于氩气、氦气、氮气、氖气、氙气和氪气等,具体可根据实际工艺条件进行选择。所述的式a所示的化合物和含有R1的化合物的摩尔比为1:(1.1-2);式b所示的化合物和含有R2的化合物的摩尔比为1:(1.1-2)。
如此,以保证式a所示的化合物和含有R1的化合物,或式b所示的化合物和含有R2的化合物之间充分反应,以获得较高的产率。当含有R1的化合物或含有R2的化合物用量过少时,可能造成式a所示的化合物或式b所示的化合物反应不完全,导致原料剩余,产率降低,且原料剩余会影响实验后续产物提纯处理;当含有R1的化合物或含有R2的化合物用量过大时,容易含有R1的化合物或含有R2的化合物药品浪费,同时也会加大实验后处理提纯的操作难度。
以下通过实施例对本发明的实施进行举例说明。实施例中涉及到的原料按照现有文献制备获得或商购获得。
实施例1
将酚噻嗪(0.99g 0.005mol)、对氟苯甲醛(0.8ml 0.0075mol)、磷酸钾(5.4g0.025mol)置于反应瓶中,除去瓶中氧气再加入无水DMF;加热至150℃;N2保护反应24h。在反应结束后冷却至室温,抽滤取液体,减压旋蒸得到粗产物。将粗产物用硅胶柱层析提纯,石油醚和四氢呋喃作为洗脱剂,最终得到黄色粉末A(0.508g,产率51%)。
将甲基三苯基溴化磷(3.5g 0.009mol)和叔丁醇钾(2.24g 0.009mol)混合到无水四氢呋喃中0℃搅拌30min,在0℃下滴加上诉黄色粉末A(1g 0.003mol);自然恢复室温反应12h。反应结束后加入甲醇再抽滤取滤液,减压旋蒸得到粗产物。将粗产物用硅胶柱层析提纯,石油醚和四氢呋喃作为洗脱剂,最终得到白色粉末B(0.9564g产率95.64%)
将白色粉末B(1.1g 0.0043mol)、2-(4-溴苯基)苯并噁唑(1g 0.0036mol)无水碳酸钾(2g 0.0146mol)、四丁基溴化铵(4.7g 0.0146mol)、三苯基磷(0.29g 0.0018mol)、醋酸钯(0.12g 0.001mol)置于反应瓶中,除去氧气,加入甲苯;升温至100℃,N2保护;反应24h。反应结束后恢复至室温加入100mL水,使用二氯甲烷进行萃取(50mL×3),合并有机相,之后将有机相用无水硫酸钠干燥后过滤,减压旋蒸得到粗产物。将粗产物用三氧化二铝柱层析提纯,石油醚和乙酸乙酯为洗脱剂进行洗脱,最终得到黄色粉末(0.56g产率56%)。1HNMR(400MHz,DMSO)δ=8.24(d,J=7.4Hz,2H),7.91(t,J=8.7Hz,4H),7.85–7.77(m,2H),7.56(s,1H),7.50–7.40(m,5H),7.12(d,J=9.4Hz,2H),6.99(s,2H),6.91(d,J=7.8Hz,2H),6.33(d,J=8.0Hz,2H).如图8所示。
其中,本实施例所涉及的合成路线如下:
实施例2
将3-甲基-9H-咔唑(0.9g 0.005mol)、对氟苯甲醛(0.8ml 0.0075mol)、磷酸钾(5.4g 0.025mol)置于反应瓶中,除去瓶中氧气再加入无水DMF;加热至150℃;N2保护反应24h。在反应结束后冷却至室温,抽滤取液体,减压旋蒸得到粗产物。将粗产物用硅胶柱层析提纯,石油醚和四氢呋喃作为洗脱剂,最终得到白色粉末A-2(0.5g,产率56%)。
将甲基三苯基溴化磷(3.5g 0.009mol)和叔丁醇钾(2.24g 0.009mol)混合到无水四氢呋喃中0℃搅拌30min,在0℃下滴加上诉白色粉末A-2(0.77g 0.003mol);自然恢复室温反应12h。反应结束后加入甲醇再抽滤取滤液,减压旋蒸得到粗产物。将粗产物用硅胶柱层析提纯,石油醚和四氢呋喃作为洗脱剂,最终得到白色粉末B-2(0.7g产率90.04%)。
将白色粉末B-2(1.22g 0.0043mol)、2-(4-溴苯基)苯并噁唑(1g 0.0036mol)无水碳酸钾(2g 0.0146mol)、四丁基溴化铵(4.7g 0.0146mol)、三苯基磷(0.29g 0.0018mol)、醋酸钯(0.12g 0.001mol)置于反应瓶中,除去氧气,加入甲苯;升温至100℃,N2保护;反应24h。反应结束后恢复至室温加入100mL水,使用二氯甲烷进行萃取(50mL×3),合并有机相,之后将有机相用无水硫酸钠干燥后过滤,减压旋蒸得到粗产物。将粗产物用硅胶层析提纯,石油醚和乙酸乙酯为洗脱剂进行洗脱,最终得到黄绿色粉末(0.64g产率64%)。
1H NMR(400MHz,DMSO)δ=8.55(m,J=7.5HZ,2H)8.03(m,J=8.0HZ,1H)7.94(m,J=8.0HZ,1H)7.77-7.73(m,6H)7.65-7.60(m,4H)7.53(m,J=7.5HZ,1H)7.38-7.35(m,4H)7.16(m,J=8.3HZ,1H)6.9(d,J=15.1HZ,2H)2.4(s,3H)
其中,本实施例所涉及的合成路线如下:
实施例3
将甲基三苯基溴化磷(3.5g 0.009mol)和叔丁醇钾(2.24g 0.009mol)混合到无水四氢呋喃中0℃搅拌30min,在0℃下滴加4-[双(4-甲氧基苯基)氨基]苯甲醛的THF溶液(1g0.003mol);自然恢复室温反应12h。反应结束后加入甲醇再抽滤取滤液,减压旋蒸得到粗产物。将粗产物用硅胶柱层析提纯,石油醚和四氢呋喃作为洗脱剂,最终得到白色粉末B-3(0.762g产率76.2%)。
将白色粉末B-3(1.42g 0.0043mol)、5-溴-2-苯基苯并噁唑(1g 0.0036mol)无水碳酸钾(2g 0.0146mol)、四丁基溴化铵(4.7g 0.0146mol)、三苯基磷(0.29g 0.0018mol)、醋酸钯(0.12g 0.001mol)置于反应瓶中,除去氧气,加入甲苯;升温至110℃,N2保护;反应24h。反应结束后恢复至室温加入100mL水,使用二氯甲烷进行萃取(50mL×3),合并有机相,之后将有机相用无水硫酸钠干燥后过滤,减压旋蒸得到粗产物。将粗产物用硅胶层析提纯,石油醚和乙酸乙酯为洗脱剂进行洗脱,最终得到黄色粉末(0.41g产率41%)。
1H NMR(400MHz,DMSO)δ=8.31(d,J=7.3HZ,1H)8.18(t,J=8.2HZ 2H)7.96(m,J=6.9HZ,1H)7.89(m,J=6.5HZ,2H)7.65(m,J=8.0HZ 2H)7.62(m,J=7.2,1H)7.46(m,J=7.5HZ,1H)7.18-7.21(m,6H)6.95(m,J=15.1HZ,2H)6.79(d,J=7.5HZ,4H)3.81(s,6H)
其中,本实施例所涉及的合成路线如下:
实施例4
将酚噻嗪(0.99g 0.005mol)、对氟苯甲醛(0.8ml 0.0075mol)、磷酸钾(5.4g0.025mol)置于反应瓶中,除去瓶中氧气再加入无水DMF;加热至150℃;N2保护反应24h。在反应结束后冷却至室温,抽滤取液体,减压旋蒸得到粗产物。将粗产物用硅胶柱层析提纯,石油醚和四氢呋喃作为洗脱剂,最终得到黄色粉末A(0.508g,产率51%)。
将甲基三苯基溴化磷(3.5g 0.009mol)和叔丁醇钾(2.24g 0.009mol)混合到无水四氢呋喃中0℃搅拌30min,在0℃下滴加上诉黄色粉末A(1g 0.003mol);自然恢复室温反应12h。反应结束后加入甲醇再抽滤取滤液,减压旋蒸得到粗产物。将粗产物用硅胶柱层析提纯,石油醚和四氢呋喃作为洗脱剂,最终得到白色粉末B(0.9564g产率95.64%)
将白色粉末B(1.1g 0.0043mol)、5-溴-2-苯基苯并噁唑(1g 0.0036mol)无水碳酸钾(2g 0.0146mol)、四丁基溴化铵(4.7g 0.0146mol)、三苯基磷(0.29g 0.0018mol)、醋酸钯(0.12g 0.001mol)置于反应瓶中,除去氧气,加入甲苯;升温至100℃,N2保护;反应24h。反应结束后恢复至室温加入100mL水,使用二氯甲烷进行萃取(50mL×3),合并有机相,之后将有机相用无水硫酸钠干燥后过滤,减压旋蒸得到粗产物。将粗产物用三氧化二铝柱层析提纯,石油醚和乙酸乙酯为洗脱剂进行洗脱,最终得到白色微黄粉末(0.36g产率36%)。
1H NMR(400MHz,DMSO)δ=8.23(d,J=5.3Hz,2H),7.89(d,J=8.0Hz,2H),7.82(d,J=8.2Hz,2H),7.75(d,J=8.1Hz,2H),7.65(s,2H),7.49(d,J=9.9Hz,2H),7.43(d,J=7.7Hz,2H),7.10(d,J=6.9Hz,2H),6.97(s,1H),6.88(s,2H),6.29(d,J=7.9Hz,2H),5.75(s,1H).
其中,本实施例所涉及的合成路线如下:
实施例5
将酚噁嗪(0.915g 0.005mol)、对氟苯甲醛(0.8ml 0.0075mol)、磷酸钾(5.4g0.025mol)置于反应瓶中,除去瓶中氧气再加入无水DMF;加热至150℃;N2保护反应24h。在反应结束后冷却至室温,抽滤取液体,减压旋蒸得到粗产物。将粗产物用硅胶柱层析提纯,石油醚和四氢呋喃作为洗脱剂,最终得到黄色粉末A-5(0.56g,产率62%)。
将甲基三苯基溴化磷(3.5g 0.009mol)和叔丁醇钾(2.24g 0.009mol)混合到无水四氢呋喃中0℃搅拌30min,在0℃下滴加上诉白色粉末A-5(0.549g 0.003mol);自然恢复室温反应12h。反应结束后加入甲醇再抽滤取滤液,减压旋蒸得到粗产物。将粗产物用硅胶柱层析提纯,石油醚和四氢呋喃作为洗脱剂,最终得到白色粉末B-5(0.5g产率91.2%)。
将白色粉末B-5(1.22g 0.0043mol)、2-(4-溴苯基)苯并噁唑(1g 0.0036mol)无水碳酸钾(2g 0.0146mol)、四丁基溴化铵(4.7g 0.0146mol)、三苯基磷(0.29g 0.0018mol)、醋酸钯(0.12g 0.001mol)置于反应瓶中,除去氧气,加入甲苯;升温至100℃,N2保护;反应24h。反应结束后恢复至室温加入100mL水,使用二氯甲烷进行萃取(50mL×3),合并有机相,之后将有机相用无水硫酸钠干燥后过滤,减压旋蒸得到粗产物。将粗产物用硅胶层析提纯,石油醚和乙酸乙酯为洗脱剂进行洗脱,最终得到淡黄色粉末(0.66g产率66%)。
1H NMR(400MHz,DMSO)δ=7.89(d,J=7.6HZ,2H)7.77(m,J=8.0HZ,2H)7.74(m,J=8.2HZ,2H)7.65(m,J=7.5HZ,2H)7.38(m,J=8.3HZ,2H)7.18(m,J=7.7HZ,2H)7.14(m,J=6.9HZ,2H)7.01(m,J=7.9HZ,2H)6.9(s,2H)
其中,本实施例所涉及的合成路线如下:
实施例6
将甲基三苯基溴化磷(3.5g 0.009mol)和叔丁醇钾(2.24g 0.009mol)混合到无水四氢呋喃中0℃搅拌30min,在0℃下滴加上诉白色粉末A-6(0.82g 0.003mol);自然恢复室温反应12h。反应结束后加入甲醇再抽滤取滤液,减压旋蒸得到粗产物。将粗产物用硅胶柱层析提纯,石油醚和四氢呋喃作为洗脱剂,最终得到白色粉末B-6(0.79g产率96.3%)
将白色粉末B-6(1.16g 0.0043mol)、5-溴-2-苯基苯并噁唑(1g 0.0036mol)无水碳酸钾(2g 0.0146mol)、四丁基溴化铵(4.7g 0.0146mol)、三苯基磷(0.29g 0.0018mol)、醋酸钯(0.12g 0.001mol)置于反应瓶中,除去氧气,加入甲苯;升温至100℃,N2保护;反应24h。反应结束后恢复至室温加入100mL水,使用二氯甲烷进行萃取(50mL×3),合并有机相,之后将有机相用无水硫酸钠干燥后过滤,减压旋蒸得到粗产物。将粗产物用三氧化二铝柱层析提纯,石油醚和乙酸乙酯为洗脱剂进行洗脱,最终得到黄色粉末(0.437g产率43.7%)。1H NMR(400MHz,DMSO)δ=8.21(m,J=5.6Hz,2H),8.00(d,1H),7.77(d,J=8.5Hz,1H),7.66(m,J=13.1Hz,4H),7.54(m,J=8.2Hz,2H),7.32(t,J=7.5Hz,4H),7.27(d,2H),7.04(m,J=7.4Hz,6H),6.98(m,J=8.1Hz,2H).
测试例1
主要考察该化合物对热,力和酸蒸汽的响应以及光波导和柔性特征。
检测化合物的力致变色性能的方法包括:将化合物的固态粉末进行研磨、溶剂熏蒸、等操作后进行紫外光照射。经观察发现,如图3所示,为实施例一的发光性能发生了变化,其发射的荧光由黄绿色变为橘黄色荧光,表明本实施例制备的化合物具有力致变色性能。具体地,初始样品在紫外光下发射黄绿色荧光,经研磨后,由黄绿色变为橘黄色荧光;此外,经研磨的样品进行二氯甲烷熏蒸,其在紫外光下由橘黄色变为黄绿色荧光。其他实施例2-6大致相同只是荧光颜色和对比度有所不同,但都能实现可逆的力致变色。图1是实施例1制备的化合物在固态下的日光下发光情况如图1所示,在固态下365nm紫外灯照射下的发光情况如图2所示。
测试例2
检测化合物的热致变色性能的方法包括:将化合物的固态粉末进行加热等操作后进行紫外光照射。经观察发现,如图4所示,实施例1的发光性能发生了变化,其发射的荧光由黄绿色变为深黄色荧光,表明本实施例制备的化合物具有热致变色性能。具体地,初始样品在紫外光下发射黄绿色荧光,经加热后,由黄绿色荧光变为深黄色荧光;此外,经冷却后,其在紫外光下荧光逐渐恢复直至恢复初始。对比实施例1,实施例6中出现加热后蓝色荧光强度变强冷却过后需要研磨才能实现可逆的热至变色效果。其他实施例都表现出和实施例1不同发射颜色的可逆变化。
测试例3
检测化合物的酸致变色性能的方法包括:将化合物的固态粉末进行酸蒸汽等操作后进行紫外光照射。经观察发现,如图5所示,实施例1的发光性能发生了变化,其发射的荧光由黄绿色荧光逐渐变深红荧光,表明本实施例制备的化合物具有酸致变色性能。具体地,初始样品在紫外光下发射黄绿色荧光,经酸蒸汽烟熏后,由黄绿色荧光变为微弱的深红色荧光;此外,再经过三乙胺烟熏后,其在紫外光下荧光逐渐恢复直至恢复初始。与实施例1不同的实施例4在经过酸刺激后表现出粉红色荧光。实施例5酸刺激后表现出深红棕色荧光并且三乙胺烟熏20min以上才能完全恢复。实施例2,3都与实施例1相似酸刺激后表现出深红色荧光。
测试例4
检测化合物的光波导性能的方法包括:将化合物的单晶进行紫外光照射。经观察发现,如图6所示,实施例1的单晶边缘发光明显比中央发光强度高,表明本实施例制备的化合物具有光波导性质。具体地,初始样品在紫外光下照射,观察单晶发光情况;对比中央与边缘的发光强度。同样的在其他实施例2-6中出现了相同的边缘发射强于晶体中央只是发射颜色,波长各有不同。
测试例5
检测化合物的柔性方法包括:将化合物的单晶进行弯曲等操作后观察其是否断裂。经观察发现,如图7所示,化合物被弯曲成拱形。表明本实施例制备的化合物具有柔性。具体地,将单晶样品两端固定逐渐向内挤压,让单晶样品形成一个拱形结构。经过弯曲后单晶样品没有出现断裂,松开固定端单晶恢复原始形状。同样的在其他实施例2-6中出现了相同现象,待力消失后单晶恢复原状。各有不同的是并非每个晶型都能实现柔性,实施例1-6中只有片状或者条状的其中一种或两种晶体可以实现。
综合上述检测结果,表明实施例1-6的化合物是一种明显的酸,力,热致变色效果同时还具有柔性以及光波导性质于一身的多元化材料。
以上所述仅为本申请的较佳实施例而已,并不用以限制本申请,凡在本申请的精神和原则之内所作的任何修改、等同替换和改进等,均应包含在本申请的保护范围之内。
Claims (2)
1.一种2-苯基苯并噁唑多刺激响应荧光材料,其特征在于,结构式如式1所示:
式1。
2.根据权利要求1所述的一种2-苯基苯并噁唑多刺激响应荧光材料的制备方法,其特征在于,将酚噻嗪0.99g 0.005mol、对氟苯甲醛0.8ml 0.0075mol、磷酸钾5.4g 0.025mol置于反应瓶中,除去瓶中氧气再加入无水DMF;加热至150℃;N2保护反应24h,在反应结束后冷却至室温,抽滤取液体,减压旋蒸得到粗产物,将粗产物用硅胶柱层析提纯,石油醚和四氢呋喃作为洗脱剂,最终得到黄色粉末A;
将甲基三苯基溴化磷3.5g 0.009mol和叔丁醇钾2.24g 0.009mol混合到无水四氢呋喃中0℃搅拌30min,在0℃下滴加上述黄色粉末A1g 0.003mol;自然恢复室温反应12h,反应结束后加入甲醇再抽滤取滤液,减压旋蒸得到粗产物,将粗产物用硅胶柱层析提纯,石油醚和四氢呋喃作为洗脱剂,最终得到白色粉末B;
将白色粉末B1.1g 0.0043mol、2-(4-溴苯基)苯并噁唑1g 0.0036mol无水碳酸钾2g0.0146mol、四丁基溴化铵4.7g 0.0146mol、三苯基磷0.29g 0.0018mol、醋酸钯0.12g0.001mol置于反应瓶中,除去氧气,加入甲苯;升温至100℃,N2保护;反应24h,反应结束后恢复至室温加入100mL水,使用二氯甲烷进行萃取50mL×3,合并有机相,之后将有机相用无水硫酸钠干燥后过滤,减压旋蒸得到粗产物,将粗产物用三氧化二铝柱层析提纯,石油醚和乙酸乙酯为洗脱剂进行洗脱,最终得到黄色粉末。
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