CN114436948A - Dipyridyl triphenylamine aldehyde fluorescent material with aggregation-induced emission effect and preparation method and application thereof - Google Patents
Dipyridyl triphenylamine aldehyde fluorescent material with aggregation-induced emission effect and preparation method and application thereof Download PDFInfo
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- CN114436948A CN114436948A CN202210057869.4A CN202210057869A CN114436948A CN 114436948 A CN114436948 A CN 114436948A CN 202210057869 A CN202210057869 A CN 202210057869A CN 114436948 A CN114436948 A CN 114436948A
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- triphenylamine
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- 239000000463 material Substances 0.000 title claims abstract description 37
- -1 Dipyridyl triphenylamine aldehyde Chemical class 0.000 title claims abstract description 27
- 230000002776 aggregation Effects 0.000 title claims abstract description 19
- 238000004220 aggregation Methods 0.000 title claims abstract description 19
- 230000000694 effects Effects 0.000 title claims abstract description 10
- 238000002360 preparation method Methods 0.000 title abstract description 6
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 claims abstract description 31
- 238000006243 chemical reaction Methods 0.000 claims abstract description 19
- 238000003384 imaging method Methods 0.000 claims abstract description 18
- 239000003292 glue Substances 0.000 claims abstract description 14
- 239000000843 powder Substances 0.000 claims abstract description 12
- 239000000758 substrate Substances 0.000 claims abstract description 11
- 238000006069 Suzuki reaction reaction Methods 0.000 claims abstract description 3
- 238000005874 Vilsmeier-Haack formylation reaction Methods 0.000 claims abstract description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 36
- 150000001875 compounds Chemical class 0.000 claims description 32
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 28
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 15
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 claims description 15
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 14
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- 229910002027 silica gel Inorganic materials 0.000 claims description 12
- 239000007864 aqueous solution Substances 0.000 claims description 10
- 239000011521 glass Substances 0.000 claims description 10
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 238000010438 heat treatment Methods 0.000 claims description 9
- 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 claims description 8
- DOOMPZOFYPSIJI-UHFFFAOYSA-N 2,3-diiodo-n,n-diphenylaniline Chemical compound IC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1I DOOMPZOFYPSIJI-UHFFFAOYSA-N 0.000 claims description 7
- 238000011161 development Methods 0.000 claims description 7
- 101000982628 Homo sapiens Prolyl 3-hydroxylase OGFOD1 Proteins 0.000 claims description 6
- 102100026942 Prolyl 3-hydroxylase OGFOD1 Human genes 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 229910001220 stainless steel Inorganic materials 0.000 claims description 6
- 239000010935 stainless steel Substances 0.000 claims description 6
- 239000012065 filter cake Substances 0.000 claims description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 5
- JLKDVMWYMMLWTI-UHFFFAOYSA-M potassium iodate Chemical compound [K+].[O-]I(=O)=O JLKDVMWYMMLWTI-UHFFFAOYSA-M 0.000 claims description 5
- 239000001230 potassium iodate Substances 0.000 claims description 5
- 229940093930 potassium iodate Drugs 0.000 claims description 5
- 235000006666 potassium iodate Nutrition 0.000 claims description 5
- 239000004033 plastic Substances 0.000 claims description 4
- 238000000967 suction filtration Methods 0.000 claims description 4
- 239000004327 boric acid Substances 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
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- 239000012043 crude product Substances 0.000 claims description 3
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- 150000003839 salts Chemical class 0.000 claims description 3
- 101100510326 Caenorhabditis elegans tpa-1 gene Proteins 0.000 claims description 2
- 125000003172 aldehyde group Chemical group 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 238000000799 fluorescence microscopy Methods 0.000 claims description 2
- QLULGIRFKAWHOJ-UHFFFAOYSA-N pyridin-4-ylboronic acid Chemical compound OB(O)C1=CC=NC=C1 QLULGIRFKAWHOJ-UHFFFAOYSA-N 0.000 claims description 2
- 150000003222 pyridines Chemical class 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 238000001953 recrystallisation Methods 0.000 claims description 2
- 238000005507 spraying Methods 0.000 claims description 2
- 239000002245 particle Substances 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 abstract description 7
- 238000003786 synthesis reaction Methods 0.000 abstract description 7
- 239000004519 grease Substances 0.000 abstract description 4
- 238000004020 luminiscence type Methods 0.000 abstract description 4
- 239000000126 substance Substances 0.000 abstract description 4
- 230000028327 secretion Effects 0.000 abstract description 3
- 230000009471 action Effects 0.000 abstract description 2
- 238000003958 fumigation Methods 0.000 abstract description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 229910052740 iodine Inorganic materials 0.000 abstract 1
- 239000011630 iodine Substances 0.000 abstract 1
- 238000006467 substitution reaction Methods 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 17
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- 238000001228 spectrum Methods 0.000 description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 239000000523 sample Substances 0.000 description 8
- 239000000543 intermediate Substances 0.000 description 7
- 230000008569 process Effects 0.000 description 7
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 6
- 238000012546 transfer Methods 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 238000000295 emission spectrum Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000007850 fluorescent dye Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 3
- PGXWDLGWMQIXDT-UHFFFAOYSA-N methylsulfinylmethane;hydrate Chemical compound O.CS(C)=O PGXWDLGWMQIXDT-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 230000005669 field effect Effects 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000013086 organic photovoltaic Methods 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 230000000171 quenching effect Effects 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- CLWRFNUKIFTVHQ-UHFFFAOYSA-N [N].C1=CC=NC=C1 Chemical group [N].C1=CC=NC=C1 CLWRFNUKIFTVHQ-UHFFFAOYSA-N 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000012984 biological imaging Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 238000007667 floating Methods 0.000 description 1
- 238000002189 fluorescence spectrum Methods 0.000 description 1
- 210000001061 forehead Anatomy 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000007781 pre-processing Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 150000001651 triphenylamine derivatives Chemical class 0.000 description 1
- 125000006617 triphenylamine group Chemical group 0.000 description 1
- SWGJCIMEBVHMTA-UHFFFAOYSA-K trisodium;6-oxido-4-sulfo-5-[(4-sulfonatonaphthalen-1-yl)diazenyl]naphthalene-2-sulfonate Chemical compound [Na+].[Na+].[Na+].C1=CC=C2C(N=NC3=C4C(=CC(=CC4=CC=C3O)S([O-])(=O)=O)S([O-])(=O)=O)=CC=C(S([O-])(=O)=O)C2=C1 SWGJCIMEBVHMTA-UHFFFAOYSA-K 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
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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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- 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"
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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
- G01N21/645—Specially adapted constructive features of fluorimeters
- G01N21/6456—Spatial resolved fluorescence measurements; Imaging
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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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- 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
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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
- 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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- 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
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Abstract
The invention discloses a dipyridine triphenylamine aldehyde fluorescent material with aggregation-induced emission effect, a preparation method and application thereof
The chemical structure is obtained by sequentially carrying out vilsmeier reaction, iodine substitution reaction and Suzuki reaction on triphenylamine. The dipyridyl triphenylamine monoaldehyde fluorescent material has a plurality of supramolecular action sites with different properties, has high affinity to fingerprint secretion, grease and the like, has the characteristics of simple synthesis, mild reaction conditions, good aggregation state luminescence property and the like, and is constructed by the dipyridyl triphenylamine monoaldehyde fluorescent materialThe aggregation-induced emission fingerprint developing agent can realize latent fingerprint imaging on various substrate surfaces in a 502 glue fumigation and powder imaging mode, and has high imaging resolution.
Description
Technical Field
The invention belongs to the field of fine chemical engineering, and particularly relates to a dipyridyl triphenylamine aldehyde fluorescent material with aggregation-induced emission effect, and a preparation method and application thereof.
Background
The fluorescence Quenching (ACQ) refers to a process in which excited electrons of an organic light-emitting molecule are inactivated by a nonradiative transition channel under a high concentration condition, and the light-emitting efficiency is reduced. With the rapid development of organic optoelectronics, fields such as organic electroluminescent devices, organic field effect devices, organic fluorescent probes, imaging reagents and the like have higher and higher requirements on the luminous performance of molecules in an aggregation state. In recent years, the appearance of Aggregation-Induced emission (AIE) Materials has greatly improved the performance of organic photovoltaic Materials in the devices, and has become one of the important directions for the development of organic photovoltaic Materials in recent years (Chemical Communications 2001(18):1740-1741.Accounts of Chemical Research 2019,52(9):2559-2570.Advanced Materials 2020,32(36): 2001457.).
The triphenylamine fluorescent material has high hole mobility, heat-resistant stability and glass transition temperature, and also has strong electron donating capability and two-photon absorption characteristic, and has important application value in the fields of fluorescent probes, multi-photon absorption, organic electroluminescent materials, organic solar cells, organic field effect transistors and the like. Due to intramolecular twisted charge transfer and extremely high planarization degree of triphenylamine and triphenylamine derivatives serving as polymer monomers, fluorescent materials containing independent triphenylamine and oligomeric triphenylamine units have extremely strong fluorescence quenching phenomena in an aggregation state, and the application value of the fluorescent materials in fluorescent probes and biological imaging is greatly reduced (J Mater Chem C2016, 4(24):5696-5701.Dyes and Pigments 2020,179: 108431.). In recent years, researches show that twisted charge transfer of triphenylamine and planarization of oligomeric triphenylamine can be inhibited by introducing a rotating unit containing double bonds and triple bonds, so that a series of triphenylamine materials capable of inducing blue light aggregation and luminescence are developed, the spectrum of the triphenylamine materials is expanded to other regions through bonding with an electron acceptor, and the application range of the triphenylamine fluorescent materials is further expanded.
Disclosure of Invention
Based on this, the first objective of the present invention is to provide a dipyridyl triphenylamine aldehyde fluorescent material with aggregation-induced emission effect, which uses triphenylamine as a chromophore core, two pyridines and an aldehyde group as an end capping unit, and has a structural formula shown in [ formula 1 ]:
the second purpose of the invention is to provide a preparation method of the dipyridyl triphenylamine aldehyde fluorescent material, wherein the synthetic route is shown as [ formula 2 ]:
the method comprises the following steps:
(a) dissolving phosphorus oxychloride in N, N-dimethylformamide, reacting in ice bath, adding triphenylamine (TPA0) recrystallized by ethanol into the reaction system, heating to 80 ℃ for reaction, and carrying out first post-treatment to obtain triphenylamine monoaldehyde (TPA 1);
(b) dissolving the compound TPA1 obtained in the step (a) in acetic acid, adding potassium iodide and potassium iodate in two batches, and heating to 80 ℃ for reaction to obtain a compound diiodotriphenylamine monoaldehyde (DITPA);
(c) and (b) adding pyridine-4-boric acid into the compound DITPA obtained in the step (b), carrying out Suzuki reaction by using tetrakis (triphenylphosphine) palladium as a catalyst, tetrahydrofuran as a solvent and a potassium carbonate aqueous solution as an alkali source, and carrying out secondary post-treatment to obtain a target compound dipyridyl triphenylamine aldehyde (DPTPTPA).
Preferably, in the step (a), the vilsmeier reaction is carried out on the triphenylamine, and the molar volume ratio of the triphenylamine to the phosphorus oxychloride to the N, N-dimethylformamide is 1.0 g: 0.6-1.5 ml: 5-12 ml; and/or the first post-treatment comprises recrystallization of the crude product with ethanol in a mass to volume ratio of 10 to 17.5.
Preferably, in the step (b), the mass fraction of the acetic acid is 36-90%, and the molar volume ratio of the triphenylamine monoaldehyde to the potassium iodide to the potassium iodate to the acetic acid is 1 mmol: 1 mmol: 1.35-1.75 mmol: 45-60 ml.
Preferably, in step (c), the molar volume ratio of diiodotriphenylamine monoaldehyde, pyridine-4-boronic acid, tetrakis (triphenylphosphine) palladium and tetrahydrofuran is 1.0 mmol: 2.05-2.10 mmol: 0.005-0.025 mmol: 2-3 ml, wherein the concentration of the potassium carbonate aqueous solution is 1.5-2.5 mol/L, the reaction temperature is 66-70 ℃, and the reaction time is 6-12 h; and/or the first post-treatment is: and cooling to room temperature after the reaction is finished, spin-drying tetrahydrofuran, adding water to dissolve and separate out salt, and performing suction filtration to obtain a filter cake, and recrystallizing the filter cake with ethanol.
The third purpose of the invention is to provide the application of the dipyridyl triphenylamine aldehyde fluorescent material in fingerprint development or latent fingerprint imaging.
The invention also provides a latent fingerprint imaging agent for preprocessing the 502 glue, which comprises the dipyridine triphenylamine aldehyde fluorescent material, and latent fingerprint fluorescence imaging is carried out by spraying the dipyridine triphenylamine aldehyde fluorescent material with an aqueous solution after the 502 glue is fumigated on the surface of a substrate.
The invention also provides a fingerprint developer of the silica gel substrate, which comprises the dipyridyl triphenylamine aldehyde fluorescent material, and can realize rapid imaging of fingerprints on various materials by adsorbing silica gel powder on the surface of the substrate for fingerprint development without using 502 glue for pretreatment.
Preferably, the substrate face is selected from a glass, plastic or stainless steel panel.
Compared with the prior art, the invention has the beneficial effects that:
the invention introduces two functional units of pyridine ring and formyl group into three phenyl groups of triphenylamine through single bond, two pyridine nitrogen atoms are topologically favorable for forming a supermolecule assembly structure between molecules in an angle of 120 degrees, rigid aromatic rings in the molecules are mutually connected by the single bond with rotation characteristic and are favorable for the de-planarization of the molecules, and the bipyridine triphenylamine monoaldehyde fluorescent material with aggregation-induced emission property is obtained, has a plurality of supermolecule action sites with different properties, improves the interaction between the triphenylamine material and biological information molecules (fatty acid, amino acid and the like), has high affinity to fingerprint secretion, grease and the like, and has the characteristics of simple synthesis, mild reaction condition, good aggregation state emission property and the like.
Secondly, the aggregation-induced emission fingerprint developer based on the dipyridyl triphenylamine aldehyde is constructed by the dipyridyl triphenylamine monoaldehyde fluorescent material, latent fingerprint imaging on various substrate surfaces of glass, stainless steel and the like is realized by two modes of 502 glue fuming and powder imaging, the imaging resolution of the fingerprint imaging is effectively improved, and the aggregation-induced emission fingerprint developer can be used in multiple fields of fluorescent probes, cell imaging, electroluminescent materials and the like and has good market prospect.
Drawings
FIG. 1 shows nuclear magnetic hydrogen spectrum of intermediate triphenylamine monoaldehyde.
FIG. 2 shows nuclear magnetic hydrogen spectrum of intermediate diiodotriphenylamine monoaldehyde.
FIG. 3 is a nuclear magnetic hydrogen spectrum of compound DPTPA.
FIG. 4 is a graph showing the absorption spectrum of the compound DPTPA in toluene, dichloromethane, tetrahydrofuran, ethyl acetate, ethanol and dimethyl sulfoxide.
FIG. 5 is a graph of the emission spectrum of the compound DPTPA in toluene, dichloromethane, tetrahydrofuran, ethyl acetate, ethanol and dimethyl sulfoxide.
FIG. 6 is a graph of the emission spectrum of the compound DPTPA in ethanol-water systems of different water contents.
Fig. 7 is a graph of the fluorescence enhancement ratio of the compound DPTPA in ethanol-water systems of different water content.
FIG. 8 is a graph of the emission spectrum of the compound DPTPA in a dimethylsulfoxide-water system with different water contents.
FIG. 9 is a graph of the fluorescence enhancement ratio of the compound DPTPA in DMSO-water systems of different water contents.
FIG. 10 is a fluorescent photograph of the compound DPTPA in ethanol and aqueous solutions.
FIG. 11 is an image of latent fingerprint samples on glass slide (a), plastic plate (b) and stainless steel (c) using 502 glue development with compound DPTPA.
FIG. 12 shows a fuming apparatus used in the gel fuming process 502; wherein, the device comprises 1-a crystallizing dish, 2-a placing table, 3-a heater, 4-a sample to be processed and 5-a glass slide.
Fig. 13 is a schematic structural view of the object placing table.
Detailed Description
In order to make the objects, technical solutions and advantages of the embodiments of the present invention clearer, the technical solutions of the embodiments of the present invention will be clearly and completely described below with reference to the drawings of the embodiments of the present invention. It is to be understood that the embodiments described are only a few embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the described embodiments of the invention without any inventive step, are within the scope of protection of the invention.
Example 1: synthesis of intermediate TPA1
Dropwise adding phosphorus oxychloride (3.6ml) into N, N-dimethylformamide (30ml) under an ice bath condition, stirring for 15 minutes, then moving to room temperature, and continuously stirring for 1 hour to obtain a reddish brown solution; triphenylamine (24.5mmol, 6g) was added to the solution, heated to 80 ℃ under nitrogen blanket, and the reaction was continued for 6 hours. After the reaction is finished, the reaction solution is cooled to room temperature, the pH value of the reaction solution is adjusted to 7-8 by using 1mol/L sodium hydroxide solution, a large amount of precipitate is obtained, light green solid TPA1(22.9mmol, 6.25g) is obtained by suction filtration, and the crude product is recrystallized by using 62.5ml of ethanol, so that purer white crystal TPA1 is obtained.
The nuclear magnetic hydrogen spectrum of triphenylamine monoaldehyde TPA1 is shown in FIG. 1: 1H NMR (400MHz, DMSO-d6) ppm 6.89(d, J ═ 8.53Hz,2H)7.17-7.28(m,6H)7.43(t, J ═ 1.00Hz,4H)7.73(d, J ═ 8.53Hz,2H)9.77(s, 1H).
Example 2: synthesis of intermediate DITPA
Triphenylamine monoaldehyde (11.0mmol, 3g) and potassium iodide (11mmol, 1.8g) were mixed with 36% acetic acid (45ml) and stirred at 80 ℃ for 1 hour, then potassium iodate (14.9mmol, 3.18g) was added and the solution immediately turned purple-red, stirring was continued with heating for 4 hours, cooled to room temperature and filtered with suction to give DITPA (8.1mmol, 4.25g) as a green solid in yield: 73.6 percent.
The nuclear magnetic hydrogen spectrum of diiodotriphenylamine monoaldehyde DITPA is shown in FIG. 2: 1H NMR (400MHz, DMSO-d6) ppm 6.96(d, J ═ 8.53Hz,4H)7.01(d, J ═ 8.53Hz,2H)7.73(d, J ═ 8.28Hz,4H)7.77(d, J ═ 8.53Hz,2H) 9.82(s, 1H).
Example 3: synthesis of compound DPPAA
Dissolving diiodotriphenylamine aldehyde (525mg, 1.0mmol) and pyridine-4-boric acid (247mg,2.0mmol) in 8ml of freshly evaporated tetrahydrofuran, then weighing a catalyst of palladium tetrakistriphenylphosphine (0.01mmol, 11.5mg) and adding into a reaction tube, injecting 0.8ml of potassium carbonate aqueous solution (1.5mol/L) under the protection of nitrogen, heating to 66 ℃ under magnetic stirring, keeping the reaction system in a slightly boiling state, reacting for 6 hours until the solution turns from yellow to reddish brown, cooling to room temperature, spin-drying tetrahydrofuran, adding water to dissolve precipitated salts, performing suction filtration, and recrystallizing the obtained filter cake with 20ml of ethanol to obtain DPTPA (0.85mmol, 365 mg) in an orange crystal shape, wherein the yield: 85 percent.
The nuclear magnetic hydrogen spectrum of dipyridyl triphenylamine aldehyde DPTPA is shown in FIG. 3: 1H NMR (400MHz, DMSO-d6) ppm 7.14(d, J ═ 8.53Hz,2H)7.32(d, J ═ 8.28Hz,4H)7.73(d, J ═ 5.02Hz,4H)7.83(d, J ═ 8.28Hz, 2H)7.88(d, J ═ 8.28Hz,4H)8.64(d, J ═ 5.02Hz,4H)9.86(s, 1H).
Nuclear magnetic hydrogen spectra of intermediate triphenylamine monoaldehyde (figure 1) and diiodotriphenylamine monoaldehyde (figure 2) shown in figures 1 and 2 show that the two intermediates have correct chemical structures, and the purity of the two intermediates after the synthesis steps meets the requirement of further synthesis.
The nuclear magnetic hydrogen spectrum of the compound DPTPA shown in figure 3 shows that the DPTPA has a correct structure, and the purity of the DPTPA synthesized by the method meets the application requirement.
Fig. 4 and 5 show the absorption spectrum (fig. 4) and emission spectrum (fig. 5) of compound dppa in toluene, dichloromethane, tetrahydrofuran, ethyl acetate, ethanol and dimethyl sulfoxide, and the results show that compound dppa shows the same absorption lines in the four solvents of toluene, tetrahydrofuran, ethyl acetate and ethanol, and shows stronger short-wave fluorescence emission in toluene and tetrahydrofuran, respectively at 450nm and 470nm, indicating that the compound shows advantageous intrinsic emission in the two solvents. In ethyl acetate, the fluorescence emission peak of the compound red-shifted to 490nm and significantly diminished, indicating that the compound exhibits intramolecular charge transfer emission in this state, while fluorescence in ethanol is completely quenched, which is caused by charge transfer with molecular twisting of the useful compound. In the absorption spectra of dichloromethane and dimethyl sulfoxide solutions, the compound DPPPA shows a new absorption peak in the long-wave region, which is also an absorption band generated by intramolecular charge transfer, while in the emission spectra of the corresponding solutions, the emission in both solutions can be found in the same long-wave region (around 540 nm), which indicates that the intramolecular charge transfer degree of the compound is stronger in both solvents.
FIGS. 6 to 9 show the fluorescence spectra and fluorescence enhancement ratio of the compound DPTPA in different water content systems: in ethanol-water systems (fig. 6 and 7) and dimethyl sulfoxide-water systems (fig. 8 and 9), it can be seen that DPTPA exhibits aggregation-induced luminescence effects in both systems, and for the original molecular luminescence dimethyl sulfoxide system, the fluorescence of the aggregation state in water also exhibits significant enhancement, proving that the compound belongs to an aggregation-induced luminescent molecular material.
Fig. 10 is a photograph of the fluorescence of the compound DPTPA in ethanol and aqueous solutions, and it can be seen that the fluorescence of the compound in aqueous solution is significantly stronger than that of ethanol solution.
Example 4: 502 glue fuming and developing process
Preparing a fingerprint sample: before taking a fingerprint sample, the volunteer washed his hands. Then, the oily part (forehead or nasal wing area) is touched by fingers, the surface is lightly rubbed to be evenly covered with grease, and the surfaces of the glass slide, the PE plastic sheet and the circular arc stainless steel reaction kettle are lightly pressed by the fingers coated with the grease.
Fumigating and displaying process: the fuming process uses the fuming device as shown in fig. 12, wherein the object placing table 2 can be selected to be a horizontal object placing table or an inclined object placing table as shown in fig. 13 according to the size of fuming objects and the fuming requirement, and a baffle plate can be additionally arranged on a round object. Selecting a crystallization dish 1 with a proper size and a placing platform 2 with a certain specification according to the fuming object, and placing the object 4 to be fuming on the placing platform 2. Pouring a certain amount 502 of glue into the crystallization dish 1 and covering the glass slide 5. The 502 glue has a slow evaporation rate, and needs to be smoked up, and a heating plate or a blower 3 can be selected for heating. Taking a blower as an example, the operation process is as follows: and (4) opening the blower, adjusting to low-grade hot air and low-grade wind speed, and slowly circling close to and along the edge of the bottom of the crystallization dish. If a heating plate is used, the bottom of the crystallization dish 1 can be directly heated, and the sample is fumigated in the crystallization dish 1 for 10 to 15 minutes.
After the fumigation is finished, the article is taken out, a small amount of DPTPA solution is absorbed by a dropper to be dripped on the surface of the article, the solution is properly covered on the fingerprint, the article is kept still for 10 minutes, then the solution on the surface of the glass slide 5 is slightly washed off by water, and the fluorescence effect of the fingerprint is observed under an ultraviolet lamp.
Example 5: preparation of silica gel-based fluorescent powder and latent fingerprint development process
Dissolving 5mg of DPTPA in 10ml of tetrahydrofuran to prepare a clear solution, adding 10g of 400-mesh 500-mesh silica gel powder, stirring for 10 minutes at room temperature, and removing the solvent by rotary evaporation to obtain yellow silica gel powder, wherein strong yellow fluorescence can be seen under an ultraviolet lamp.
A fingerprint sample was prepared as in example 4, and a small amount of silica gel powder was dipped with a hairbrush and the surface of the sample was lightly swept to obtain a powder-imaged fingerprint sample. If necessary, the sample surface can be purged with an ear washing bulb to remove the virtually floating fluorescent powder.
Fig. 11 shows latent fingerprint imaging photographs (fig. 11a and 11b) which are fumigated by glue 502 and latent fingerprint imaging photographs (fig. 11c) which are powder imaging carried by silica gel, and it can be seen that latent fingerprint imaging can be successfully realized on the surfaces of glass and metal substrates by two different developing methods, while the silica gel-based powder has better imaging effect on the metal surface and lower background fluorescence, which indicates that the interaction of the compound on fingerprint secretion through pyridine and formyl groups is better than the indirect contact type imaging which is fumigated and shaped by glue 502.
The embodiments described above are intended to facilitate a person of ordinary skill in the art in understanding and using the invention. It will be readily apparent to those skilled in the art that various modifications can be made to the embodiments and the generic principles defined herein may be applied to other embodiments without the use of the inventive faculty. Therefore, the present invention is not limited to the above-mentioned embodiments, and those skilled in the art should make improvements and modifications within the scope of the present invention based on the disclosure of the present invention.
Claims (10)
1. The dipyridine triphenylamine aldehyde fluorescent material with aggregation-induced emission effect takes triphenylamine as a chromophore core, takes two pyridines and one aldehyde group as an end capping unit, and has the formula 1]The structural formula shown in the specification:
2. the method for preparing a dipyridyl triphenylamine aldehyde fluorescent material with aggregation-induced emission effect according to claim 1, wherein the synthetic route is as shown in [ formula 2 ]:
the method comprises the following steps:
(a) dissolving phosphorus oxychloride in N, N-dimethylformamide, reacting in ice bath, adding a compound triphenylamine (TPA0) recrystallized by ethanol into the reaction system, heating to 80 ℃ for reaction, and carrying out primary post-treatment to obtain a compound triphenylamine monoaldehyde (TPA 1);
(b) dissolving the compound TPA1 obtained in the step (a) in acetic acid, adding potassium iodide and potassium iodate in two batches, and heating to 80 ℃ for reaction to obtain a compound diiodotriphenylamine monoaldehyde (DITPA);
(c) and (b) adding pyridine-4-boric acid into the compound DITPA obtained in the step (b), carrying out Suzuki reaction by using tetrakis (triphenylphosphine) palladium as a catalyst, tetrahydrofuran as a solvent and a potassium carbonate aqueous solution as an alkali source, and carrying out secondary post-treatment to obtain a target compound dipyridyl triphenylamine aldehyde (DPTPTPA).
3. The method for preparing dipyridyl triphenylamine aldehyde fluorescent material according to claim 2, wherein in the step (a), the vilsmeier reaction is performed on triphenylamine, and the molar volume ratio of triphenylamine, phosphorus oxychloride and N, N-dimethylformamide is 1.0 g: 0.6-1.5 ml: 5-12 ml; and/or the first post-treatment comprises recrystallization of the crude product with ethanol in a mass to volume ratio of 10 to 17.5.
4. The method for preparing dipyridyl triphenylamine aldehyde fluorescent material according to claim 2, wherein in the step (b), the mass fraction of acetic acid is 36% -90%, and the molar volume ratio of triphenylamine monoaldehyde, potassium iodide, potassium iodate and acetic acid is 1 mmol: 1 mmol: 1.35-1.75 mmol: 45-60 ml.
5. The method for preparing a dipyridyl triphenylamine aldehyde fluorescent material according to claim 2, wherein in the step (c), the molar volume ratio of diiodo triphenylamine monoaldehyde, pyridine-4-boronic acid, tetrakis (triphenylphosphine) palladium and tetrahydrofuran is 1.0 mmol: 2.05-2.10 mmol: 0.005-0.025 mmol: 2-3 ml, wherein the concentration of the potassium carbonate aqueous solution is 1.5-2.5 mol/L, the reaction temperature is 66-70 ℃, and the reaction time is 6-12 h; and/or the first post-treatment is: and cooling to room temperature after the reaction is finished, spin-drying tetrahydrofuran, adding water to dissolve and separate out salt, and performing suction filtration to obtain a filter cake, and recrystallizing the filter cake with ethanol.
6. The use of the dipyridyl triphenylamine aldehyde fluorescent material according to claim 1 in fingerprint development or latent fingerprint imaging.
7. A latent fingerprint imaging agent pretreated by glue 502, which comprises the dipyridyl triphenylamine aldehyde fluorescent material described in claim 1, wherein latent fingerprint fluorescence imaging is performed by spraying the dipyridyl triphenylamine aldehyde fluorescent material in an aqueous solution after the glue 502 is smoked on the substrate surface.
8. The latent fingerprint imaging agent pre-treated with glue 502 of claim 7, wherein the substrate surface is selected from a glass, plastic or stainless steel panel.
9. A silica gel-based fingerprint developer comprising the dipyridyl triphenylamine aldehyde fluorescent material according to claim 1, wherein the fingerprint developer is prepared by adsorbing silica gel powder onto the surface of the substrate.
10. The silica gel-based fingerprint developer according to claim 9, wherein the substrate surface is selected from glass, plastic or stainless steel panels, and the silica gel powder has a particle size of 400-500 mesh.
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116855100A (en) * | 2023-06-17 | 2023-10-10 | 青岛科技大学 | Triphenylamine dye capable of being directly used for latent fingerprint development and preparation method and application thereof |
Citations (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102093740A (en) * | 2011-01-21 | 2011-06-15 | 电子科技大学 | Organic dye for dye sensitized solar cell and preparation method of organic dye |
| CN103524404A (en) * | 2013-10-23 | 2014-01-22 | 东南大学 | Pyridine-triphenylamine-anthracene conjugated molecule with aggregation-induced emission property and preparation method thereof |
| CN103896830A (en) * | 2014-03-24 | 2014-07-02 | 东南大学 | Triphenylamine pyridinium salt fluorescent molecule and preparation method thereof |
| CN105670608A (en) * | 2016-02-23 | 2016-06-15 | 安徽大学 | High-selectivity fluorescent probe capable of detecting nickel ions in mitochondria of living cells and preparation method thereof |
| CN107602449A (en) * | 2017-09-12 | 2018-01-19 | 常州工程职业技术学院 | A kind of preparation and application of the Zn complex fluorescence probe with graphite-like structure |
| CN108409642A (en) * | 2018-05-11 | 2018-08-17 | 安徽大学 | A kind of two-photon fluorescence probe and preparation method thereof of secondary identification copper ion and Hcy |
| CN108727256A (en) * | 2018-06-29 | 2018-11-02 | 华中科技大学 | A kind of photosensitizer and the preparation method and application thereof based on the more pyridiniujms of triphenylamine |
| CN112174839A (en) * | 2020-11-05 | 2021-01-05 | 四川大学华西医院 | Lipid drop specific labeled fluorescent probe and synthetic method and application thereof |
| CN112321527A (en) * | 2020-11-05 | 2021-02-05 | 四川大学华西医院 | Lipid drop targeted fluorescent probe and synthetic method and application thereof |
| CN112625673A (en) * | 2020-12-18 | 2021-04-09 | 山东农业大学 | Amphiphilic host-guest fluorescent material capable of rapidly identifying potential fingerprints and preparation method and application thereof |
| CN113582931A (en) * | 2021-07-13 | 2021-11-02 | 上海师范大学 | Fluorescent dye probe for latent fingerprint detection and preparation method and application thereof |
| CN113788861A (en) * | 2021-10-14 | 2021-12-14 | 山东普力强生物科技有限公司 | Metal iridium (III) complex and preparation method and application thereof |
-
2022
- 2022-01-19 CN CN202210057869.4A patent/CN114436948A/en active Pending
Patent Citations (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102093740A (en) * | 2011-01-21 | 2011-06-15 | 电子科技大学 | Organic dye for dye sensitized solar cell and preparation method of organic dye |
| CN103524404A (en) * | 2013-10-23 | 2014-01-22 | 东南大学 | Pyridine-triphenylamine-anthracene conjugated molecule with aggregation-induced emission property and preparation method thereof |
| CN103896830A (en) * | 2014-03-24 | 2014-07-02 | 东南大学 | Triphenylamine pyridinium salt fluorescent molecule and preparation method thereof |
| CN105670608A (en) * | 2016-02-23 | 2016-06-15 | 安徽大学 | High-selectivity fluorescent probe capable of detecting nickel ions in mitochondria of living cells and preparation method thereof |
| CN107602449A (en) * | 2017-09-12 | 2018-01-19 | 常州工程职业技术学院 | A kind of preparation and application of the Zn complex fluorescence probe with graphite-like structure |
| CN108409642A (en) * | 2018-05-11 | 2018-08-17 | 安徽大学 | A kind of two-photon fluorescence probe and preparation method thereof of secondary identification copper ion and Hcy |
| CN108727256A (en) * | 2018-06-29 | 2018-11-02 | 华中科技大学 | A kind of photosensitizer and the preparation method and application thereof based on the more pyridiniujms of triphenylamine |
| CN112174839A (en) * | 2020-11-05 | 2021-01-05 | 四川大学华西医院 | Lipid drop specific labeled fluorescent probe and synthetic method and application thereof |
| CN112321527A (en) * | 2020-11-05 | 2021-02-05 | 四川大学华西医院 | Lipid drop targeted fluorescent probe and synthetic method and application thereof |
| CN112625673A (en) * | 2020-12-18 | 2021-04-09 | 山东农业大学 | Amphiphilic host-guest fluorescent material capable of rapidly identifying potential fingerprints and preparation method and application thereof |
| CN113582931A (en) * | 2021-07-13 | 2021-11-02 | 上海师范大学 | Fluorescent dye probe for latent fingerprint detection and preparation method and application thereof |
| CN113788861A (en) * | 2021-10-14 | 2021-12-14 | 山东普力强生物科技有限公司 | Metal iridium (III) complex and preparation method and application thereof |
Non-Patent Citations (7)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116855100A (en) * | 2023-06-17 | 2023-10-10 | 青岛科技大学 | Triphenylamine dye capable of being directly used for latent fingerprint development and preparation method and application thereof |
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