CN107118757A - A kind of diarylethene organic photochromic material based on furans and its preparation method and application - Google Patents
A kind of diarylethene organic photochromic material based on furans and its preparation method and application Download PDFInfo
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- CN107118757A CN107118757A CN201710271280.3A CN201710271280A CN107118757A CN 107118757 A CN107118757 A CN 107118757A CN 201710271280 A CN201710271280 A CN 201710271280A CN 107118757 A CN107118757 A CN 107118757A
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- 239000000463 material Substances 0.000 title claims abstract description 55
- 150000002240 furans Chemical class 0.000 title claims abstract description 31
- 150000001988 diarylethenes Chemical class 0.000 title claims abstract description 23
- 238000002360 preparation method Methods 0.000 title claims abstract description 19
- -1 aldehyde compound Chemical class 0.000 claims abstract description 29
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims abstract description 27
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 20
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 claims abstract description 16
- 239000003054 catalyst Substances 0.000 claims abstract description 12
- 229910052763 palladium Inorganic materials 0.000 claims abstract description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 12
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000006243 chemical reaction Methods 0.000 claims abstract description 8
- 235000011009 potassium phosphates Nutrition 0.000 claims abstract description 8
- 238000001228 spectrum Methods 0.000 claims abstract description 8
- 229910000160 potassium phosphate Inorganic materials 0.000 claims abstract description 7
- 238000001816 cooling Methods 0.000 claims abstract description 6
- 239000002070 nanowire Substances 0.000 claims abstract description 6
- 238000010992 reflux Methods 0.000 claims abstract description 6
- PNWFXPGGROADNS-UHFFFAOYSA-N 1,2-dibromocyclopentene Chemical compound BrC1=C(Br)CCC1 PNWFXPGGROADNS-UHFFFAOYSA-N 0.000 claims abstract description 5
- 238000000605 extraction Methods 0.000 claims abstract 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 claims description 17
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 9
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims description 9
- 230000008859 change Effects 0.000 claims description 6
- 238000003384 imaging method Methods 0.000 claims description 6
- 238000006392 deoxygenation reaction Methods 0.000 claims description 5
- 235000011056 potassium acetate Nutrition 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 238000004440 column chromatography Methods 0.000 claims description 4
- 125000004185 ester group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical group 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- ZZPNDIHOQDQVNU-UHFFFAOYSA-N 2-hydroxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound CC1(C)OB(O)OC1(C)C ZZPNDIHOQDQVNU-UHFFFAOYSA-N 0.000 claims description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical class C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 230000005693 optoelectronics Effects 0.000 claims description 2
- 230000005622 photoelectricity Effects 0.000 claims description 2
- 230000002441 reversible effect Effects 0.000 claims description 2
- 239000004327 boric acid Substances 0.000 claims 2
- BMIBJCFFZPYJHF-UHFFFAOYSA-N 2-methoxy-5-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine Chemical compound COC1=NC=C(C)C=C1B1OC(C)(C)C(C)(C)O1 BMIBJCFFZPYJHF-UHFFFAOYSA-N 0.000 claims 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims 1
- 230000031709 bromination Effects 0.000 claims 1
- 238000005893 bromination reaction Methods 0.000 claims 1
- 238000001914 filtration Methods 0.000 abstract 1
- 238000011031 large-scale manufacturing process Methods 0.000 abstract 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 7
- 238000011160 research Methods 0.000 description 7
- 0 Cc([o]c(*)c1)c1C(CCC1)=C1c1c(C)[o]c(*)c1 Chemical compound Cc([o]c(*)c1)c1C(CCC1)=C1c1c(C)[o]c(*)c1 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000001963 growth medium Substances 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 238000010609 cell counting kit-8 assay Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Natural products O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 229930192474 thiophene Natural products 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- JIOVMLYJNWPYPJ-UHFFFAOYSA-N C=C.S1C=CC=C1.S1C=CC=C1 Chemical group C=C.S1C=CC=C1.S1C=CC=C1 JIOVMLYJNWPYPJ-UHFFFAOYSA-N 0.000 description 2
- 239000005864 Sulphur Substances 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 238000006073 displacement reaction Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- AFVDZBIIBXWASR-UHFFFAOYSA-N (e)-1,3,5-hexatriene Chemical group C=CC=CC=C AFVDZBIIBXWASR-UHFFFAOYSA-N 0.000 description 1
- VWGRESZTMULPDE-UHFFFAOYSA-N 2-bromo-5-methylfuran Chemical class CC1=CC=C(Br)O1 VWGRESZTMULPDE-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 229910002666 PdCl2 Inorganic materials 0.000 description 1
- 208000032825 Ring chromosome 2 syndrome Diseases 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- DAJLHNABGVYSOO-UHFFFAOYSA-N boric acid;2,3-dimethylbutane-2,3-diol Chemical class OB(O)O.CC(C)(O)C(C)(C)O DAJLHNABGVYSOO-UHFFFAOYSA-N 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 230000007541 cellular toxicity Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 231100000433 cytotoxic Toxicity 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- 230000003013 cytotoxicity Effects 0.000 description 1
- 231100000135 cytotoxicity Toxicity 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 125000001706 diarylethene group Chemical group 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 206010016256 fatigue Diseases 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000013642 negative control Substances 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000003746 solid phase reaction Methods 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K9/00—Tenebrescent materials, i.e. materials for which the range of wavelengths for energy absorption is changed as a result of excitation by some form of energy
- C09K9/02—Organic tenebrescent materials
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/001—Preparation for luminescence or biological staining
- A61K49/0013—Luminescence
- A61K49/0017—Fluorescence in vivo
- A61K49/0019—Fluorescence in vivo characterised by the fluorescent group, e.g. oligomeric, polymeric or dendritic molecules
- A61K49/0021—Fluorescence in vivo characterised by the fluorescent group, e.g. oligomeric, polymeric or dendritic molecules the fluorescent group being a small organic molecule
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
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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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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
- G01N21/643—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" non-biological material
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
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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
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
- G01N2021/6432—Quenching
Abstract
The invention provides a kind of Novel diaryl ethene organic photochromic material based on furans, its structural formula as shown in formula I,, the invention provides the preparation method of above-mentioned photochromic material, in reaction vessel, by substituted single aldehyde compound based on diarylethene, dibromo cyclopentene, potassium phosphate, palladium catalyst, DMF or dioxane or tetrahydrofuran or toluene, in under 20 DEG C to reflux temperature, react 1 24 hours, after cooling, filtering, extraction, is spin-dried for, post is crossed, the diaryl ethylene compounds described in formula I are obtained.The preparation method of the present invention is simple and direct efficiently, and yield is high, and good economy performance, the value with large-scale production is environmentally friendly.The present invention has strong spectrum property, available for preparing multihoming electrogen switch, molecular wire element and prepare photochromic luminescent device etc..
Description
Technical field
The invention belongs to materialogy field, it is related to a kind of green organic photochromic material, specifically one kind is based on
Diarylethene organic photochromic material of furans and its preparation method and application.
Background technology
The theory of bistable state diarylethene is proposed first from Masahiro Irie in 1988, and diarylethene just causes
People extensive research interests.By the development of nearly 30 years, diarylethene was in photoelectric device, information storage, biology
Each neighborhood such as imaging, sensing, false proof, display shows huge application value.For organic photochromic material, letter
The read-write of breath uses full photon mode, so it is always researcher's pursuit that design, which prepares high performance organic photochromic material,
Target.Photochromism refers to a compound in the light irradiation by certain wavelength, can occur specific chemistry anti-
Product should be obtained, in the presence of the light irradiation or heat of another wavelength, is recovered again to original molecular structure, with this property
The material of matter is known as photochromic material.The species of organic photochromic material is various, wherein, diarylethene derivatives point
1,3,5- hexatrienes fragment in son can carry out conrotatory by appropriate conformation under low wavelength light irradiation and form 6 π-electronics
Closed loop state, this makes diaryl ethylene compounds have good heat endurance (heat irreversible), excellent endurance, height
Conversion ratio and quantum yield, fast response speed and outstanding solid phase reaction activity, many merits cause on diaryl second
The research Showed Very Brisk of alkenes photochromic material, and in the storage of VHD optical information, light-operated molecular wire, molecular logic
The photoelectric field such as equipment and optical drive device shows the prospect of being widely applied and vigorous vitality.
Dithiazole ethylene compound is good with stability as diarylethene structure the most classical, and good is anti-
Fatigability and bi-stable character, by extensive research and application.But, containing heavy atom in di-thiofuran ethylene structure --- sulphur is former
Son, limits its application in biological field and environment-friendly materials.Therefore the diarylethene of Development of Novel degradable green
Organic photochromic material seems particularly urgent.Furans is one of simplest heterocyclic aromatic compounds, is had very with thiophene
Similar chemical constitution and electronic property.Furan nucleus has been widely used for building pi-conjugated molecule, furan derivatives have with
Under advantage：(1) sulphur atom is replaced on the one hand to reduce armaticity with oxygen, molecule has more quinoid structure features so that
π-electronics preferably delocalization；On the other hand oxidizing potential can be reduced so that HOMO orbital energy levels are raised, therefore are conducive to hole
Injection and transmission.(2) thiophene contains relatively heavy sulphur atom, occurs interior change because heavy atom produces rotation rail coupling
(ISC), so the problem of causing optical quenching, compared to thiophen semiconductors, with outstanding photoluminescent property, therefore can use
To prepare organic semiconductor luminescent device, including electroluminescent material (OLEDs) and organic light-emitting transistor (OLETs).(3) furan
Compound of muttering has less armaticity, and intermolecular π-π interactions are smaller, so solubility is relatively large.(4) furans is raw
Biodegradable material, can be prepared, this causes it to be more suitable for large-scale application from biorenewable raw material.But it is due to past people
Be mistakenly considered furan compound less stable (Gidron O, Diskin-Posner Y, Bendikov M.r- always
Oligofurans[J].Journal of the American Chemical Society,2010,132(7):2148-
2150) so that for less (Yamaguchi T, the Irie M.Photochromic and of the relative thiophene of research of furans
fluorescent properties of bisfurylethene derivatives[J].Journal of Materials
Chemistry,2006,16(48):4690-4694).Relative to the research of di-thiofuran ethylene material, the diaryl based on furans
The photochromic research of ethene has bigger application prospect with application.Therefore, diarylethene of the developmental research based on furans
Molecule photochromic material, studies it and switchs spectrum property, bio-imaging, structure and preparation technology, to development multihoming photoelectricity
Molecular switch, molecular wire element, photochromic luminescent device etc. and its application are of great immediate significance.
The content of the invention
For above-mentioned technical problem of the prior art, the invention provides a kind of organic photochromic material based on furans
Material and its preparation method and application, described this organic photochromic material and its preparation method and application can be solved existing
There is the higher technical problem of organic photochromic material complex synthetic route, cost in technology, while can realize in biology
Application in imaging, bio-sensing and environment-friendly materials.
The invention provides a kind of organic photochromic material based on furans, its structural formula as shown in formula I,
Wherein, R is selected from aldehyde radical, carboxyl, ester group, halogen, H, C1~C12Alkyl, alkoxy or phenyl.
Present invention also offers the preparation method of the above-mentioned organic photochromic material based on furans, comprise the following steps：
In reaction vessel, by substituted single aldehyde compound based on diarylethene, dibromo cyclopentene, potassium phosphate,
Palladium catalyst, DMF or dioxane or tetrahydrofuran or toluene, are added in reaction system, in 20 DEG C to times
At a temperature of stream, react 1-12 hours, obtain two furans ethylene compounds described in formula I, its structural formula is as follows,
Wherein, R is selected from aldehyde radical, carboxyl, ester group, halogen, H, C1~C12Alkyl, alkoxy or phenyl.
The course of reaction of above-mentioned preparation method is as follows,
1) one the step of prepare furan boronic acid ester, during furan boronic acid ester is prepared, furans bromide, connection are weighed
Boric acid pinacol ester, potassium acetate, palladium catalyst, DMF or dioxane or tetrahydrofuran, described furans bromine
The material of compound, connection boric acid pinacol ester, potassium acetate, palladium catalyst, N, N-dimethylformamide or dioxane or tetrahydrofuran
Than for 50.0~100.0mmol：100.0~200.0mmol：150.0~300.0mmol：2.5~5.0mmol:100~
200mL；After deoxygenation, then in 20 DEG C to reflux temperature, react 24-48 hours, after cooling, extract, be spin-dried for, column chromatography obtains institute
State furan boronic acid ester type compound；
2) the step of two furans cyclopentene of preparation, during the described furans cyclopentene of preparation two, weighs ring
Amylene dibromo, furan boronic acid ester, potassium phosphate, palladium catalyst, N, N-dimethylformamide or dioxane or tetrahydrofuran or first
Benzene, described cyclopentene dibromo, furan boronic acid ester, potassium phosphate, palladium catalyst, DMF or dioxane or four
The material ratio of hydrogen furans or toluene is 1.0~2.0mmol：2.0~4.0mmol：5.0~6.0mmol：0.1~0.2mmol:10
~20mL；After deoxygenation, then in 20 DEG C to reflux temperature, react 1-24 hours, after cooling, extract, be spin-dried for, column chromatography obtains institute
State diaryl ethylene compounds.
Present invention also offers the above-mentioned diarylethene organic photochromic material based on furans in molecular switch spectrum
Application in performance.
Specifically, under solution state, color and/or the reversible change of fluorescence are produced under Uv and visible light irradiation.
Present invention also offers a kind of above-mentioned diarylethene organic photochromic material based on furans in bio-imaging
In application.
It is many in preparation present invention also offers a kind of above-mentioned diarylethene organic photochromic material based on furans
Address electrogen switch, molecular wire element；Prepare the application in the optoelectronic information such as photochromic luminescent device field.
The raw material that the present invention is used can be prepared using the conventional method of document, will not be repeated here.
The present invention can be in pure organic solution (such as：Toluene, acetonitrile, dimethyl sulfoxide (DMSO), n-hexane, dichloromethane) in,
The lower change for producing color and/or fluorescence of Uv and visible light irradiation.
The present invention is due to using the diarylethene based on furans for system, and prepared material does not contain element sulphur, property
Matter is stable, is a kind of new green material with molecular switch spectrum property.
The present invention with based on diarylmethylidenefuran derivative class compound and dibromo cyclopentene formation diaryl ethylene compounds,
Under palladium catalyst effect, method is unified into using new metal pair, synthesis step is less, high income and cost of material
Cheap, technique is easy to industrialized production, and product purification is efficiently convenient, and prepared photochromic material has high light conversion effect
Rate, quick photoresponse ability, good heat endurance and outstanding endurance.
The present invention is compared with prior art, and its technological progress is significant.Molecular switch spectrum property of the present invention
Organic photochromic material there is high phototranstormation efficiency, quick photoresponse ability, good heat endurance and outstanding
Endurance, can be applied to photoelectric field as intellectual material.The present invention has strong spectrum property, available for preparing multihoming
Electrogen switch, molecular wire element and prepare photochromic luminescent device etc..Material of the present invention has biology
Degradability and fluorescent characteristic, can be used in the fields such as bio-imaging and bio-sensing.
Brief description of the drawings
During Fig. 1 is embodiment 2, organic photochromic material DFC (1, the 2- bis- (5- formoxyl -2- first that the present invention is provided
Base -3- furyls) cyclopentene) acetonitrile solution (10 μm of olL-1) different illumination (365nm monochromatic sources) time (1min,
2min, 3min, 4min, 5min, 6min, 7min, 8min, 9min, 10min, 11min, 12min, 13min, 14min, 15min,
16min, 17min, 18min, 19min, 20min, 21min, 22min) under abosrption spectrogram, abscissa is wavelength, ordinate
For absorbance；
During Fig. 2 is embodiment 2, acetonitrile solution (the 10 μm of olL for the organic photochromic material DFC that the present invention is provided-1)
Different illumination (365nm monochromatic sources) time (1min, 2min, 3min, 4min, 5min, 6min, 7min, 8min, 9min,
Fluorescence emission spectrogram of compound under 10min), abscissa is wavelength, and ordinate is florescent intensity value.
During Fig. 3 is embodiment 3, the present invention provides organic photochromic material DFC and DTC (1,2- bis- (5- formoxyls -2-
Methyl -3- thienyls) cyclopentene) in cytotoxic comparison diagram, abscissa is organic photochromic material concentration, and ordinate is
Versus cell activity.
Embodiment
Below by embodiment, the invention will be further elaborated, and its purpose, which is only that, more fully understands that the present invention's is interior
Hold.Therefore, the cited case is not intended to limit protection scope of the present invention.
Described room temperature is in the following example：25-28℃；Raw materials used and reagent is commercially available product or normal using document
It is prepared by the method for rule.
Embodiment 1 (organic photochromic material DFC synthesis)：
Compound DFC synthesis
The preparation method of the bromo- 5- methylfurans -2- formaldehyde (compound 2) of 4- is referring to document (Sysoiev D, Fedoseev
A,Kim Y,et al.Synthesis and Photoswitching Studies of
Difurylperfluorocyclopentenes with Extendedπ‐Systems[J].Chemistry–A European
Journal,2011,17(24):6663-6672.)
5- methyl -4- (ring -2- bases of 4,4,5,5- tetramethyl -1,3,2- dioxies boron penta) furans -2- formaldehyde (compound 3)
Preparation method.250ml there-necked flasks N2Displacement gas three times, N2Under protection, 9.45g compounds 2 (50mmol) are sequentially added,
19.05g connection boric acid pinacol esters (75mmol), 14.7g potassium acetates (150mmol) and 1.83g PdCl2dppf(2.5mmol)。
It is eventually adding the DMF after strict deoxygenation.Stirring reaction 48 hours at 80 DEG C.Layer post analysis (eluent PE:EA=10：1), obtain
9.8g faint yellow solids, 83% yield.1H NMR(400MHz,CDCl3)δ(ppm):1.306(s,12H),2.551(s,3H),
2.05(m,6H),7.353(s,1H),9.485(s,1H).13C NMR(100MHz,CDCl3)δ(ppm):14.517,24.818,
24.989,83.454,83.768,128.831,151.791,168.727,176.723.HRMS(EI+,m/z):[M]+calcd
for C12H17O4B,235.1256；found,235.1251.IR(KBr)νmax(cm-1):451.4,505.0,518.7,547.4,
576.7,638.5,666.9,699.7,714.8,758.4,809.4,852.4,951.7,960.3,999.7,1052.6,
1108.7,1119.6,1146.7,1170.6,1210.9,1251.0,1286.2,1316.7,1336.4,1380.2,1428.2,
1534.3,1588.3,1678.7,2359.7,2733.1,2817.3,2930.9,2979.7,3338.1,3644.9,3666.5,
3730.1,3849.0.
There-necked flask N2Displacement gas three times, N2Under protection, 110mg cyclopentene dibromo (0.946mmol), 490mg are sequentially added
Compound 3 (2.08mmol), 1.2g potassium phosphates (5.68mmol) and 110mg Pd (PPh3)4(0.095mmol), is eventually adding and removes
100 DEG C are stirred overnight under the conditions of the DMF 20ml of oxygen, lucifuge.Layer post analysis (eluent PE:EA=5：1) 190mg, is obtained faint yellow
Solid DFC, 63.5% yield.1H NMR(400MHz,CDCl3)δ(ppm):2.055(m,2H),2.099(s,6H),2.752(t,
J 7.6Hz,4H),7.006(s,2H),9.456(s,2H).13C NMR(100MHz,CDCl3)δ(ppm):13.732,22.424,
37.821,120.880,122.865,130.553,151.044,155.668,176.891.HRMS(EI+,m/z):[M]+
calcd for C17H16O4,284.1049；found,284.1052.IR(KBr)νmax(cm-1):423.4,458.9,495.9,
522.5,545.7,575.6,631.2,673.0,682.7,770.4,781.5,846.1,858.2,867.8,884.1,
918.2,950.4,975.1,1004.0,1028.4,1041.1,1068.2,1119.7,1171.8,1213.3,1305.0,
1320.5,1336.0,1371.9,1410.9,1428.3,1442.0,1520.6,1679.0,2819.9,2847.9,2915.8,
2961.5,3085.9,3186.4,3337.5,3436.4.
Embodiment 2 (organic photochromic material DFC photochromic properties)：
The compound DFC of above-mentioned gained is dissolved in acetonitrile, it is 10 μm of olL to be configured to concentration-1Acetonitrile solution.In band
There is the solution to be measured that 2.5mL is added in 1cm × 1cm × 4cm quartz colorimetric utensils of stirring, using 365nm monochromatic sources according to not
Duration together (1min, 2min, 3min, 4min, 5min, 6min, 7min, 8min, 9min, 10min, 11min, 12min,
13min, 14min, 15min, 16min, 17min, 18min, 19min, 20min, 21min, 22min) solution to be measured is shone
Penetrate, and absorption spectrum is determined using ultraviolet-visible spectrophotometer, as a result as shown in Figure 1.Under 365nm ultraviolet lights, inhale
Receive spectrum and occur a new absworption peak at 520nm, and extension over time gradually increases to and reaches photostationary state, simultaneously
Solution colour is also changed into pink from colourless.Under visible ray (>=550nm) irradiation, absorption spectrum reforms into original state
And solution colour takes off.The change in fluorescence of above-mentioned solution is studied with sepectrophotofluorometer, using 326nm as excitation wavelength,
As a result it is as shown in Figure 2.It can be seen that the fluorescence emission peak that maximum wavelength is located at 460nm is gradually quenched with the extension of light application time.Say
The bright luminous organic material has typical photochromic properties.
Embodiment 3 (organic photochromic material DFC biologic applications)：
Compound DFC (1,2- bis- (5- formoxyl -2- methyl-3-furyls) cyclopentene) and DTC ((the 5- formyls of 1,2- bis-
Base -2- methyl -3- thienyls) cyclopentene) cytotoxicity, be by Cell counting Kit -8 (CCK-8) quantitative determine.It is real
In testing, by MC3T3-E1 cells (derive from Shanghai Branch of Chinese Academy of Sciences cell bank) in MEM- α culture mediums with 1.0 × 104
The density of individual cells/well is inoculated into 96 orifice plates.After cell growth 12 hours, culture medium is replaced by the change containing various concentration
Compound DFC and DTC new culture medium (200 μ L/ holes).Before CCK-8 measure is carried out, with containing 20 μ L CCK-8 solution
Culture medium new 200 μ L replaces the culture medium of back, and cell is further incubated for 48 hours.After being incubated 3 hours, enzyme mark is used
Instrument (Multiskan Mk 3) determines the absorbance at 450nm in each hole.Calculated by calculating versus cell vigor quantitatively thin
Cellular toxicity, 100% viability, the SDS of various concentrations are defined as by the control group not treated in culture medium with any material
Positive and negative control is respectively set to compound DFC, DTC.As a result as shown in figure 3, explanation organic photochromic material DFC
There is no toxicity to cell.In 100 μM of maximum concentration, cell survival rate is more than 99%.
Claims (7)
1. a kind of diarylethene organic photochromic material based on furans, it is characterised in that：Its structural formula such as formula I institutes
Show,
Wherein, R is selected from aldehyde radical, carboxyl, ester group, halogen, H, C1~C12Alkyl, alkoxy or phenyl.
2. a kind of preparation method of diarylethene organic photochromic material based on furans described in claim 1, it is special
Levy and be：In reaction vessel, by substituted single aldehyde compound based on diarylethene, dibromo cyclopentene, potassium phosphate, palladium
Catalyst, DMF or dioxane or tetrahydrofuran or toluene, under 20 DEG C to reflux temperature, react 1-24
Hour, after cooling, filter, extraction is spin-dried for, and is crossed post, is obtained the diaryl ethylene compounds described in formula I, its structural formula is as follows
It is shown,
Wherein, R is selected from aldehyde radical, carboxyl, ester group, halogen, H, C1~C12Alkyl, alkoxy or phenyl.
3. a kind of preparation method of diarylethene organic photochromic material based on furans according to claim 2,
It is characterized in that comprising the following steps：
1) one the step of prepare furan boronic acid ester, during furan boronic acid ester is prepared, furans bromide, connection boric acid are weighed
Pinacol ester, potassium acetate, palladium catalyst, DMF or dioxane or tetrahydrofuran, described furans bromination
The material ratio of thing, connection boric acid pinacol ester, potassium acetate, palladium catalyst, N, N-dimethylformamide or dioxane or tetrahydrofuran
For 50.0~100.0mmol：100.0~200.0mmol：150.0~300.0mmol：2.5~5.0mmol:100~200mL；
After deoxygenation, then in 20 DEG C to reflux temperature, react 24-48 hours, after cooling, extract, be spin-dried for, column chromatography obtains the furans
Boric acid ester compound；
2) the step of two furans cyclopentene of preparation, during the described furans cyclopentene of preparation two, weighs cyclopentene
Dibromo, furan boronic acid ester, potassium phosphate, palladium catalyst, DMF or dioxane or tetrahydrofuran or toluene, institute
Cyclopentene dibromo, furan boronic acid ester, potassium phosphate, palladium catalyst, the N stated, N-dimethylformamide or dioxane or tetrahydrofuran
Or the material ratio of toluene is 1.0~2.0mmol：2.0~4.0mmol：5.0~6.0mmol：0.1~0.2mmol:10~20mL；
After deoxygenation, then in 20 DEG C to reflux temperature, react 1-24 hours, after cooling, extract, be spin-dried for, column chromatography obtains two virtue
Base ethylene compounds.
4. the diarylethene organic photochromic material based on furans is in molecular switch spectrum property described in claim 1
Using.
5. application as claimed in claim 4, it is characterised in that：Under solution state, produced under Uv and visible light irradiation
The reversible change of color and/or fluorescence.
6. a kind of the answering in bio-imaging of diarylethene organic photochromic material based on furans described in claim 1
With.
7. a kind of diarylethene organic photochromic material based on furans described in claim 1 is preparing multihoming photoelectricity
Molecular switch, molecular wire element；Prepare the application in the optoelectronic information such as photochromic luminescent device field.
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