CN116478125A - Fluorescent organic small molecular material, preparation method and application thereof - Google Patents
Fluorescent organic small molecular material, preparation method and application thereof Download PDFInfo
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- CN116478125A CN116478125A CN202310429080.1A CN202310429080A CN116478125A CN 116478125 A CN116478125 A CN 116478125A CN 202310429080 A CN202310429080 A CN 202310429080A CN 116478125 A CN116478125 A CN 116478125A
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- fluorescent
- fluorescent organic
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- 239000000463 material Substances 0.000 title claims abstract description 54
- 238000002360 preparation method Methods 0.000 title claims abstract description 20
- 150000003384 small molecules Chemical class 0.000 claims abstract description 17
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000005859 coupling reaction Methods 0.000 claims abstract description 8
- 239000000178 monomer Substances 0.000 claims abstract description 8
- 239000000843 powder Substances 0.000 claims abstract description 7
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical class [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910021626 Tin(II) chloride Inorganic materials 0.000 claims abstract description 6
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000004327 boric acid Substances 0.000 claims abstract description 6
- 229910052796 boron Inorganic materials 0.000 claims abstract description 6
- -1 boron ester Chemical class 0.000 claims abstract description 6
- 239000000203 mixture Substances 0.000 claims abstract description 6
- 239000000654 additive Substances 0.000 claims abstract description 5
- 239000000945 filler Substances 0.000 claims abstract description 5
- 230000000996 additive effect Effects 0.000 claims abstract description 3
- 239000011230 binding agent Substances 0.000 claims abstract description 3
- 238000005496 tempering Methods 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 6
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- BKQXUNGELBDWLS-UHFFFAOYSA-N 9,9-diphenylfluorene Chemical compound C1=CC=CC=C1C1(C=2C=CC=CC=2)C2=CC=CC=C2C2=CC=CC=C21 BKQXUNGELBDWLS-UHFFFAOYSA-N 0.000 claims description 2
- 238000006619 Stille reaction Methods 0.000 claims description 2
- 238000006069 Suzuki reaction reaction Methods 0.000 claims description 2
- 239000002318 adhesion promoter Substances 0.000 claims description 2
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 claims description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000010440 gypsum Substances 0.000 claims description 2
- 229910052602 gypsum Inorganic materials 0.000 claims description 2
- 239000000314 lubricant Substances 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000002245 particle Substances 0.000 claims description 2
- 239000004014 plasticizer Substances 0.000 claims description 2
- 229910052711 selenium Inorganic materials 0.000 claims description 2
- 239000000377 silicon dioxide Substances 0.000 claims description 2
- 239000003381 stabilizer Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000005909 Kieselgur Substances 0.000 claims 1
- 239000000454 talc Substances 0.000 claims 1
- 229910052623 talc Inorganic materials 0.000 claims 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 abstract description 12
- 239000000126 substance Substances 0.000 abstract description 5
- 239000007850 fluorescent dye Substances 0.000 abstract description 4
- 238000000227 grinding Methods 0.000 abstract description 2
- 238000002156 mixing Methods 0.000 abstract description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- 238000005086 pumping Methods 0.000 description 19
- 238000012360 testing method Methods 0.000 description 15
- 238000004140 cleaning Methods 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- 238000001816 cooling Methods 0.000 description 10
- 238000000921 elemental analysis Methods 0.000 description 10
- 238000010438 heat treatment Methods 0.000 description 10
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 10
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- 239000012300 argon atmosphere Substances 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 9
- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 description 8
- 238000013365 molecular weight analysis method Methods 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 230000004580 weight loss Effects 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 238000000295 emission spectrum Methods 0.000 description 2
- 238000002189 fluorescence spectrum Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000005424 photoluminescence Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
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- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/08—Hydrogen atoms or radicals containing only hydrogen and carbon atoms
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- C07C13/54—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings
- C07C13/547—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings at least one ring not being six-membered, the other rings being at the most six-membered
- C07C13/567—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings at least one ring not being six-membered, the other rings being at the most six-membered with a fluorene or hydrogenated fluorene ring system
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- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/40—Benzopyrazines
- C07D241/44—Benzopyrazines with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
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- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/14—Thiadiazoles; Hydrogenated thiadiazoles condensed with carbocyclic rings or ring systems
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- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
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Abstract
A fluorescent organic small molecular material, a preparation method and application thereof relate to the technical field of fluorescent materials and solve the problems of poor chemical structure stability and shorter service life of the existing organic fluorescent dye. The organic small molecule is a fluorenyl derivative connected with a benzene center core Ar. The preparation method comprises the steps of connecting a bromomonomer of a central core Ar with boron ester, boric acid or tin salt monomers of fluorene and derivatives thereof through a palladium-catalyzed coupling reaction single bond to obtain a fluorescent organic micromolecular material; or the boron ester, boric acid or tin salt monomer of the central core Ar and the bromomonomer of fluorene and derivatives thereof are connected by a single bond through palladium-catalyzed coupling reaction; obtaining the fluorescent organic small molecular material. The anti-counterfeiting ink is prepared by uniformly mixing the fluorescent organic micromolecular material serving as fluorescent powder with a binder, a filler and an additive, grinding the mixture by a grinder, and finally tempering the mixture. The invention can be applied to the field of fluorescence anti-counterfeiting.
Description
Technical Field
The invention relates to the technical field of fluorescent materials, in particular to a fluorescent organic small molecular material, a preparation method and application thereof.
Background
With the development of society, people are deepening the utilization of energy, and a plurality of novel functional materials are extended. In luminescent materials, photoluminescent-based materials absorb external light radiation, emit light of other wavelengths after excitation, and the materials have wide application in the fields of special display, anti-counterfeiting, night coating, emergency lighting and the like. The inorganic photoluminescent material has the defects of less variety, poor adjustability, harsh use conditions and the like. In contrast, organic photoluminescent materials are various in variety, adjustable in luminescent property, soluble in specific solvents, convenient to process, and widely focused in the fields of new-generation flat panel display, fluorescent anti-counterfeiting and the like.
In the organic luminescent material, the high polymer has poor batch and result repeatability due to the polydispersibility of the structure, the luminescent material based on the small organic molecule has definite structure, no repeatability problem and is easy to study the relationship between the structure and the performance; in addition, the small molecules are easier to regulate in terms of solubility. Thus, photoluminescent materials based on small organic molecules are increasingly gaining attention.
In the field of fluorescent anti-counterfeiting materials, development of light-colored fluorescent materials is needed. Such materials are required to have lighter colors per se, i.e. to absorb in the near ultraviolet region, and at the same time are required to have higher photoluminescence properties, i.e. to exhibit vivid fluorescence under banknote validators or ultraviolet light for anti-counterfeiting use. In practical application, the organic molecules are easy to crystallize or oxidize, and the material has short service life due to insufficient chemical structure stability, and is easy to fail under long-time ultraviolet irradiation. Therefore, how to solve the problem of poor stability of the existing organic fluorescent dye through reasonable chemical structure design, developing a light-color fluorescent organic small-molecule dye with high stability and long service life has become one of the problems to be solved by many researchers in the field.
Disclosure of Invention
In order to solve the problems of poor chemical structure stability and short service life of the existing organic fluorescent dye, the invention provides a fluorescent organic small molecular material, a preparation method and application thereof.
The technical scheme of the invention is as follows:
a fluorescent organic small molecular material has the structural formula:
wherein Ar is
R 1 is-Ph,
R 2 Is H, -F, -Cl, -CH3, -OCH3 or-CN;
R 3 is H, -CN, -Ph,
X is O, S or Se;
m is an integer of 0 to 20, n is an integer of 0 to 10, x is an integer of 1 to 20, and y is an integer of 1 to 20.
Preferably, the structural formula is:
the preparation method of the fluorescent organic small molecular material comprises the following steps:
the brominated monomer of the central core Ar is connected with boron ester of fluorene and derivative thereof, boric acid or tin salt monomer through palladium-catalyzed coupling reaction single bond, so as to obtain a fluorescent organic micromolecular material;
or the boron ester, boric acid or tin salt monomer of the central core Ar and the bromomonomer of fluorene and derivatives thereof are connected by a single bond through palladium-catalyzed coupling reaction; obtaining the fluorescent organic small molecular material.
Preferably, the fluorene is spirofluorene or 9, 9-diphenylfluorene.
Preferably, the coupling reaction is a Suzuki coupling reaction or a Stille coupling reaction.
The fluorescent organic small molecular material is used as fluorescent powder to be applied to fluorescent anti-counterfeiting materials.
An anti-counterfeiting ink is prepared by uniformly mixing the fluorescent organic micromolecular material serving as fluorescent powder with a binder, a filler and an additive, grinding the mixture by a grinder, and finally tempering the mixture; the ratio of the fluorescent organic small molecular material is 0.5% -20%.
Preferably, the particle size of the grinded fluorescent organic small molecular material is 10 nm-500 nm.
Preferably, the filler is one or a mixture of at least two of colloidal calcium carbonate, aluminum hydroxide, gypsum powder, silicon dioxide, talcum powder or diatomite.
Preferably, the additives include plasticizers, stabilizers, lubricants, adhesion promoters, driers, and leveling agents.
Compared with the prior art, the invention solves the problems of poor chemical structure stability and shorter service life of the organic fluorescent dye, and has the following specific beneficial effects:
1. the organic micromolecules provided by the invention are fluorenyl derivatives connected with benzene center core Ar, the initial side band of the absorption spectrum is between 300 and 450nm, the micromolecules are in lighter color, meanwhile, the micromolecules have higher fluorescence quantum efficiency, the maximum peak of the fluorescence spectrum is between 490 and 570nm, and the organic micromolecules are strong green light emission, can be used as fluorescent anti-counterfeiting materials for preparing anti-counterfeiting ink or anti-counterfeiting ink, and have great application prospects in the fluorescent anti-counterfeiting field;
2. the organic micromolecule provided by the invention has moderate solubility, can be dissolved in a specific solvent, and is convenient to prepare anti-counterfeiting ink or anti-counterfeiting ink; the film has extremely high stability, can resist high temperature and ultraviolet irradiation in a film state, can be applied to actual production, and has long service life;
3. the preparation method of the organic micromolecule provided by the invention has the advantages of simple steps and low cost, and is convenient for mass preparation and actual production.
Drawings
FIG. 1 is a nuclear magnetic resonance spectrum of a small fluorescent organic molecule 30 in example 9;
FIG. 2 is a graph showing the emission spectrum of the fluorescent small organic molecule 30 in example 9;
FIG. 3 is a graph showing the thermal weight loss of small fluorescent organic molecules 30 in example 9.
Detailed Description
In order to make the technical solution of the present invention clearer, the technical solution of the embodiments of the present invention will be clearly and completely described below with reference to the accompanying drawings of the present invention, and it should be noted that the following embodiments are only used for better understanding of the technical solution of the present invention, and should not be construed as limiting the present invention.
Example 1.
The fluorescent organic small molecule 1 based on fluorene units is prepared in the embodiment, and the structural formula is shown as follows:
the synthetic route of the fluorescent organic small molecule 1 is as follows:
the preparation method comprises the following specific steps:
a500 mL double-necked flask and a roast flask were taken, and 5.0g of Compound 1-1, 15.8g of Compound 1-2, and 1.0g of Pd (PPh) 3 ) 4 And 5 drops of Aliquat336, pumping and ventilating for three times, adding 250mL of ultra-dry toluene and 50mL of 2M aqueous potassium carbonate solution under the protection of argon atmosphere, heating and refluxing at 100 ℃ for reaction for 24 hours, naturally cooling to room temperature, and repeatedly cleaning filter residues after pumping and filtering to obtain 10.5g of fluorescent small organic molecules 1, wherein the yield is 80.8%.
Elemental analysis structure (C) 56 H 32 N 2 S) theoretical value: c,87.93; s,4.19; n,3.66; h,4.22; test value: c,87.98; s,4.13; n,3.62; h,4.27.
MALDI-TOF molecular weight analysis theory: 764.2, experimental values: 764.2.
example 2.
The fluorescent organic small molecule 23 based on fluorene units is prepared in the embodiment, and the structural formula is shown as follows:
the synthetic route of the fluorescent small organic molecule 23 is as follows:
the preparation method comprises the following specific steps:
a500 mL double-necked flask and a roast flask were taken, and 5.0g of Compound 23-1, 14.1g of Compound 1-2, and 0.9g of Pd (PPh) 3 ) 4 And 5 drops of Aliquat336, pumping and ventilating for three times, adding 250mL of ultra-dry toluene and 50mL of 2M aqueous potassium carbonate solution under the protection of argon atmosphere, heating and refluxing at 100 ℃ for reaction for 24 hours, naturally cooling to room temperature, and repeatedly cleaning filter residues after pumping and filtering to obtain 9.9g of fluorescent small organic molecules 23, wherein the yield is 81.8%.
Elemental analysis structure (C) 56 H 30 F 2 N 2 S) theoretical value: c,83.98; h,3.78; f,4.74; n,3.50; s,4.00; test value: c,83.94; h,3.82; f,4.77; n,3.53; s,3.94.
MALDI-TOF molecular weight analysis theory: 800.2, experimental values: 800.2.
example 3.
The fluorescent organic small molecule 24 based on fluorene units is prepared in the embodiment, and the structural formula is shown as follows:
the synthetic route of the fluorescent small organic molecule 24 is as follows:
the preparation method comprises the following specific steps:
a500 mL double-necked flask and a roast flask were taken, and 5.0g of Compound 24-1, 12.8g of Compound 1-2, and 0.8g of Pd (PPh) 3 ) 4 And 5 drops of Aliquat336, pumping and ventilating for three times, adding 250mL of ultra-dry toluene and 50mL of 2M aqueous potassium carbonate solution under the protection of argon atmosphere, heating and refluxing at 100 ℃ for reaction for 24 hours, naturally cooling to room temperature, and repeatedly cleaning filter residues after pumping and filtering to obtain 9.2g of fluorescent small organic molecules 24, wherein the yield is 80.5%.
Elemental analysis junctionStructure (C) 56 H 30 Cl 2 N 2 S) theoretical value: c,80.67; h,3.63; cl,8.50; n,3.36; s,3.84; test value: c,80.72; h,3.61; cl,8.52; n,3.33; s,3.82.
MALDI-TOF molecular weight analysis theory: 833.8, experimental values: 833.8.
example 4.
The present example prepared a fluorescent organic small molecule 25 based on fluorene units, the structural formula of which is shown as follows:
the synthetic route of the fluorescent small organic molecule 25 is as follows:
the preparation method comprises the following specific steps:
a500 mL double-necked flask and a roast flask were taken, and 5.0g of Compound 25-1, 14.4g of Compound 1-2, and 0.9g of Pd (PPh) 3 ) 4 And 5 drops of Aliquat336, pumping and ventilating for three times, adding 250mL of ultra-dry toluene and 50mL of 2M aqueous potassium carbonate solution under the protection of argon atmosphere, heating and refluxing at 100 ℃ for reaction for 24 hours, naturally cooling to room temperature, and repeatedly cleaning filter residues after pumping and filtering to obtain 9.6g of fluorescent small organic molecules 25, wherein the yield is 78.2%.
Elemental analysis structure (C) 56 H 36 N 2 S) theoretical value: c,87.85; h,4.58; n,3.53; s,4.04; test value: c,87.88; h,4.52; n,3.51; s,4.09.
MALDI-TOF molecular weight analysis theory: 792.3, experimental values: 792.3.
example 5.
The present example prepared a fluorene unit-based fluorescent small organic molecule 26 having the following structural formula:
the synthetic route of the fluorescent small organic molecules 26 is as follows:
the preparation method comprises the following specific steps:
a500 mL double-necked flask and a roast flask were taken, and 5.0g of Compound 26-1, 13.1g of Compound 1-2, and 0.8g of Pd (PPh) 3 ) 4 And 5 drops of Aliquat336, pumping and ventilating for three times, adding 250mL of ultra-dry toluene and 50mL of 2M aqueous potassium carbonate solution under the protection of argon atmosphere, heating and refluxing at 100 ℃ for reaction for 24 hours, naturally cooling to room temperature, and repeatedly cleaning filter residues after pumping and filtering to obtain 9.5g of fluorescent small organic molecules 26, wherein the yield is 81.6%.
Elemental analysis structure (C) 58 H 36 N 2 O 2 S), theoretical value: c,84.44; h,4.40; n,3.40; o,3.88; s,3.89. Test value: c,84.47; h,4.41; n,3.37; o,3.84; s,3.91.
MALDI-TOF molecular weight analysis theory: 824.3, experimental values: 824.3.
example 6.
The present example prepared a fluorene unit-based fluorescent small organic molecule 27 having the following structural formula:
the synthetic route of the fluorescent small organic molecule 27 is as follows:
the preparation method comprises the following specific steps:
a500 mL double-necked flask and a roast flask were taken, and 5.0g of Compound 27-1, 13.5g of Compound 1-2, and 0.7g of Pd (PPh) 3 ) 4 And 5 drops of Aliquat336, pumping three times, adding 250mL of ultra-dry toluene and 50mL of 2M under the protection of argon atmosphereAnd (3) carrying out heating reflux reaction on the potassium carbonate aqueous solution for 24 hours at the temperature of 100 ℃, naturally cooling to room temperature, and repeatedly cleaning filter residues after suction filtration to obtain 9.4g of fluorescent organic micromolecules 27 with the yield of 79.5%.
Elemental analysis structure (C) 58 H 30 N 4 S), theoretical value: c,85.48; h,3.71; n,6.87; s,3.93. Test value: c,85.43; h,3.74; n,6.82; s,4.01.
MALDI-TOF molecular weight analysis theory: 764.2, experimental values: 764.2.
example 7.
The present example prepared a fluorene unit-based fluorescent small organic molecule 28 having the following structural formula:
the synthetic route of the fluorescent small organic molecules 28 is as follows:
the preparation method comprises the following specific steps:
a500 mL double-necked flask and a roast flask were taken, and 5.0g of Compound 28-1, 16.7g of Compound 1-2, and 1.0g of Pd (PPh) 3 ) 4 And 5 drops of Aliquat336, pumping and ventilating for three times, adding 250mL of ultra-dry toluene and 50mL of 2M aqueous potassium carbonate solution under the protection of argon atmosphere, heating and refluxing at 100 ℃ for reaction for 24 hours, naturally cooling to room temperature, and repeatedly cleaning filter residues after pumping and filtering to obtain 10.3g of fluorescent small organic molecules 28, wherein the yield is 76.5%.
Elemental analysis structure (C) 56 H 32 N 2 O) theoretical value: c,89.82; h,4.31; n,3.74; o,2.14; test value: c,89.85; h,4.30; n,3.78; o,2.07.
MALDI-TOF molecular weight analysis theory: 748.3, experimental values: 748.3.
example 8.
The present example prepared a fluorene unit-based fluorescent small organic molecule 29 having the following structural formula:
the synthetic route of the fluorescent small organic molecule 29 is as follows:
the preparation method comprises the following specific steps:
a500 mL double-necked flask and a roast flask were taken, and 5.0g of Compound 29-1, 13.6g of Compound 1-2, and 0.8g of Pd (PPh) 3 ) 4 And 5 drops of Aliquat336, pumping and ventilating for three times, adding 250mL of ultra-dry toluene and 50mL of 2M aqueous potassium carbonate solution under the protection of argon atmosphere, heating and refluxing at 100 ℃ for reaction for 24 hours, naturally cooling to room temperature, and repeatedly cleaning filter residues after pumping and filtering to obtain 9.7g of fluorescent organic micromolecules 29 with the yield of 81.2%.
Elemental analysis structure (C) 56 H 32 N 2 Se) theoretical value: c,82.85; h,3.97; n,3.45; se,9.73; test value: c,82.83; h,3.99; n,3.48; se,9.70.
MALDI-TOF molecular weight analysis theory: 812.2, experimental values: 812.2.
example 9.
The structural formula of the fluorescent organic small molecule 30 based on fluorene units is shown as follows:
the synthetic route of the fluorescent small organic molecule 30 is as follows:
the preparation method comprises the following specific steps:
taking 500mL double-mouth bottle, baking bottle, adding 5.0g of compound 30-1 and 15.9g of compound30-2，1.0gPd(PPh 3 ) 4 And 5 drops of Aliquat336, pumping and ventilating for three times, adding 250mL of ultra-dry toluene and 50mL of 2M aqueous potassium carbonate solution under the protection of argon atmosphere, heating and refluxing at 100 ℃ for reaction for 24 hours, naturally cooling to room temperature, and repeatedly cleaning filter residues after pumping and filtering to obtain 10.6g of fluorescent small organic molecules 30, wherein the yield is 81.2%.
The nuclear magnetic hydrogen spectrum test is carried out on the fluorescent organic micromolecular material prepared in the embodiment, the test spectrum is shown in figure 1, and the test result is as follows: 1 H NMR(500MHz,CDCl 3 ):δ(ppm)7.99(d,J＝7.9Hz,2H),7.90(d,J＝7.9Hz,2H),7.84(s,2H),7.82(d,J＝7.5Hz,2H),7.52(s,2H),7.44(d,J＝7.6Hz,2H)7.39(t,J＝7.6Hz,2H),7.31-7.27(m,10H),7.25-7.18(m,12H).
it can be proved that the embodiment successfully synthesizes the structural formula asIs a small molecule material of (a).
Elemental analysis (C) of the fluorescent organic small molecule material prepared in this example 56 H 36 N 2 S), theoretical value: c,87.47; h,4.72; n,3.64; s,4.17. Test value: c,87.44; h,4.71; n,3.67; s,4.18.
MALDI-TOF analysis was performed, theoretical values: 768.3, experimental values: 768.3.
the fluorescent organic micromolecule material prepared by the embodiment is subjected to an emission spectrum test, and the test result is shown in fig. 2, and the maximum peak of the fluorescence spectrum is 490-570 nm, so that the fluorescent organic micromolecule material is strong green light emission, can be used as a fluorescent anti-counterfeiting material for preparing anti-counterfeiting ink or anti-counterfeiting ink, and has a great application prospect in the fluorescent anti-counterfeiting field.
The thermal weight loss analysis is carried out on the fluorescent organic micromolecular material prepared in the embodiment, and the result is shown in fig. 3, and the material is completely unchanged below 100 ℃, slight weight loss occurs above 100 ℃, and the high-speed decomposition is started when the temperature reaches approximately 400 ℃. The fluorescent organic small molecular material prepared by the embodiment has extremely high stability and high temperature resistance.
Example 10.
The present example prepared a fluorescent organic small molecule 31 based on fluorene units, the structural formula of which is shown as follows:
the synthetic route of the fluorescent small organic molecule 31 is as follows:
the preparation method comprises the following specific steps:
a500 mL double-necked flask and a roast flask were taken, and 5.0g of Compound 23-1, 14.1g of Compound 30-2, and 0.9g of Pd (PPh) 3 ) 4 And 5 drops of Aliquat336, pumping and ventilating for three times, adding 250mL of ultra-dry toluene and 50mL of 2M aqueous potassium carbonate solution under the protection of argon atmosphere, heating and refluxing at 100 ℃ for reaction for 24 hours, naturally cooling to room temperature, and repeatedly cleaning filter residues after pumping and filtering to obtain 9.3g of fluorescent small organic molecules 31, wherein the yield is 76.6%.
Elemental analysis structure (C) 56 H 34 F 2 N 2 S), theoretical value: c,83.56; h,4.26; f,4.72; n,3.48; s,3.98. Test value: c,83.59; h,4.28; f,4.70; n,3.44; s,3.99.
MALDI-TOF analysis, theoretical values: 804.2, experimental values: 804.2.
it is apparent that the above examples are given by way of illustration only and are not limiting of the embodiments. Other variations or modifications of the above teachings will be apparent to those of ordinary skill in the art. It is not necessary here nor is it exhaustive of all embodiments. While still being apparent from variations or modifications that may be made by those skilled in the art are within the scope of the invention.
Claims (10)
1. A fluorescent organic small molecular material is characterized by having a structural formula:
wherein Ar is
R 1 is-Ph,
R 2 Is H, -F, -Cl, -CH3, -OCH3 or-CN;
R 3 is H, -CN, -Ph,
X is O, S or Se;
m is an integer of 0 to 20, n is an integer of 0 to 10, x is an integer of 1 to 20, and y is an integer of 1 to 20.
2. The fluorescent organic small molecule material of claim 1, wherein the structural formula is:
3. a method for preparing the fluorescent organic small molecule material according to claim 1 or 2, wherein the preparation method comprises the following steps:
the brominated monomer of the central core Ar is connected with boron ester of fluorene and derivative thereof, boric acid or tin salt monomer through palladium-catalyzed coupling reaction single bond, so as to obtain a fluorescent organic micromolecular material;
or the boron ester, boric acid or tin salt monomer of the central core Ar and the bromomonomer of fluorene and derivatives thereof are connected by a single bond through palladium-catalyzed coupling reaction; obtaining the fluorescent organic small molecular material.
4. The method for preparing a fluorescent organic small molecule material according to claim 3, wherein the fluorene is spirofluorene or 9, 9-diphenylfluorene.
5. The method for preparing a fluorescent organic small molecule material according to claim 3, wherein the coupling reaction is a Suzuki coupling reaction or a Stille coupling reaction.
6. The use of the fluorescent organic small molecular material according to claim 1 or 2, wherein the fluorescent organic small molecular material is used as fluorescent powder in fluorescent anti-counterfeiting materials.
7. An anti-counterfeiting ink is characterized in that the fluorescent organic micromolecular material in claim 1 or 2 is taken as fluorescent powder, and is uniformly mixed with a binder, a filler and an additive, and then is ground by a grinder, and finally is subjected to tempering to obtain the anti-counterfeiting ink; the ratio of the fluorescent organic small molecular material is 0.5% -20%.
8. The anti-forgery ink of claim 7, wherein the particle size of the milled fluorescent organic small molecule material is 10nm to 500nm.
9. The anti-forgery ink of claim 7, wherein the filler is one or a mixture of at least two of colloidal calcium carbonate, aluminum hydroxide, gypsum powder, silica, talc, or diatomaceous earth.
10. The anti-counterfeit ink according to claim 7, wherein the additives include plasticizers, stabilizers, lubricants, adhesion promoters, driers and leveling agents.
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| WO2004002970A1 (en) * | 2002-06-29 | 2004-01-08 | Covion Organic Semiconductors Gmbh | 2,1,3-benzothiadiazoles for use as electronic active components |
| US20060052612A1 (en) * | 2002-06-29 | 2006-03-09 | Covion Organic Semiconductors Gmbh Intellectual Property Group | 2,1,3-Benothiadiazoles for use as electronic active components |
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