CN117510523A - Preparation and application of seven-membered N, N heterocyclic compound - Google Patents

Preparation and application of seven-membered N, N heterocyclic compound Download PDF

Info

Publication number
CN117510523A
CN117510523A CN202311351468.0A CN202311351468A CN117510523A CN 117510523 A CN117510523 A CN 117510523A CN 202311351468 A CN202311351468 A CN 202311351468A CN 117510523 A CN117510523 A CN 117510523A
Authority
CN
China
Prior art keywords
fluorescent
mmol
bodipy
formylpyrrole
ethylindole
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
CN202311351468.0A
Other languages
Chinese (zh)
Inventor
张诺诺
张驰
晏佳莹
王璇
王龙
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
China Three Gorges University CTGU
Original Assignee
China Three Gorges University CTGU
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by China Three Gorges University CTGU filed Critical China Three Gorges University CTGU
Priority to CN202311351468.0A priority Critical patent/CN117510523A/en
Publication of CN117510523A publication Critical patent/CN117510523A/en
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C07F5/022—Boron compounds without C-boron linkages
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B42—BOOKBINDING; ALBUMS; FILES; SPECIAL PRINTED MATTER
    • B42D—BOOKS; BOOK COVERS; LOOSE LEAVES; PRINTED MATTER CHARACTERISED BY IDENTIFICATION OR SECURITY FEATURES; PRINTED MATTER OF SPECIAL FORMAT OR STYLE NOT OTHERWISE PROVIDED FOR; DEVICES FOR USE THEREWITH AND NOT OTHERWISE PROVIDED FOR; MOVABLE-STRIP WRITING OR READING APPARATUS
    • B42D25/00—Information-bearing cards or sheet-like structures characterised by identification or security features; Manufacture thereof
    • B42D25/30—Identification or security features, e.g. for preventing forgery
    • B42D25/36—Identification or security features, e.g. for preventing forgery comprising special materials
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B57/00—Other synthetic dyes of known constitution
    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • C09K2211/1055—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with other heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
    • C09K2211/107—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms with other heteroatoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Indole Compounds (AREA)

Abstract

The invention discloses a preparation method and application of a seven-membered N, N heterocyclic compound, wherein 3, 3-dimethyl-2-ethylindole and 2-formylpyrrole are used as raw materials, and a seven-membered N, N-fluoboron fluorescent dye is finally generated through Knoevenagel condensation reaction under the action of a triethylamine catalyst. The dye can be combined with acrylic resin on a film to form a film quickly, and when the concentration is low, the dye presents a transparent color when being irradiated by natural light, clear yellow fluorescence can be seen under an ultraviolet lamp, the front-back contrast difference degree is obvious, and the distinction degree is high. The fluorescent dye has the advantages of simple synthesis method, higher fluorescence quantum yield, low manufacturing cost and great potential in the fields of fluorescence holographic anti-counterfeiting packaging films, OLDE and the like.

Description

Preparation and application of seven-membered N, N heterocyclic compound
Technical Field
The invention relates to a fluorescent dye, in particular to the technical field of fluorescent material anti-counterfeiting films.
Background
Under the irradiation of ultraviolet light (200-400 nm), special ink with different colors of light rays (400-800 nm) can be seen. The wavelength of the light of the excitation light source can be divided into short-wave ultraviolet excitation fluorescent anti-counterfeiting ink (excitation wavelength 254 nm) and long-wave ultraviolet excitation fluorescent anti-counterfeiting ink (excitation wavelength 365 nm). Fluorescent anti-counterfeiting ink can be classified into colored fluorescent ink (a certain color exists under natural light irradiation) and colorless fluorescent ink (colorless and invisible under natural light irradiation).
The fluorescent anti-counterfeiting film is usually an anti-counterfeiting mode with a fluorescent anti-counterfeiting layer, the fluorescent anti-counterfeiting layer determines the performance of the anti-counterfeiting film, the common anti-counterfeiting layer solution is to dope dye or pigment with resin, so that the dye or pigment is uniformly dispersed and stably connected through the resin, and a unique optical phenomenon can be shown under the action of a specific wavelength light source or other external factors, so that the anti-counterfeiting purpose is achieved. At present, the dye used for fluorescence anti-counterfeiting has insufficient performance, short-wave emission is easily influenced by an environmental light source, and lower solid fluorescence quantum yield does not have covering power and is easily covered by the same dye fluorescence. Therefore, it is necessary to improve the optical properties of dyes in the field of fluorescent anti-counterfeiting.
Disclosure of Invention
The invention aims to overcome the technical problems and provide a novel BODIPY fluorescent dye. The fluorescent dye has the advantages of simple synthesis method, higher fluorescence quantum yield, easy synthesis, low manufacturing cost and the structural formula shown as follows:
the synthesis method of the invention comprises the following synthesis paths:
the method comprises the following steps:
(1) Adding 3, 3-dimethyl-2-ethylindole, 2-formylpyrrole and toluene into a reaction bottle at room temperature, heating and refluxing, and then adding piperidine and acetic acid to obtain a reaction liquid 1;
(2) Adding triethylamine into the reaction solution 1 in the step (1), and heating and refluxing boron trifluoride diethyl etherate to obtain a reaction solution 2;
(3) And (3) respectively washing the reaction liquid 2 in the step (2) with water, extracting with an extracting agent, drying, eluting with a column layer eluent, purifying, and performing rotary evaporation to obtain solid products YJ-1FB, YJ-2FB and YJ-3FB.
In the step (1), the feeding mole ratio of the 3, 3-dimethyl-2-ethylindole to the 2-formylpyrrole is 1:1-10.
The heating reflux temperature of the step (1) is 100-150 ℃ and the heating time is 1-6 hours.
The feeding sequence of the step (1) is 3, 3-dimethyl-2-ethylindole, 2-formylpyrrole, toluene, triethylamine and boron trifluoride diethyl etherate.
The extractant in the step (2) is dichloromethane: petroleum ether=1:1, YJ-1FB is eluted from column chromatography eluent petroleum ether: dichloromethane = 2:1, YJ-2FB, YJ-3FB from eluent petroleum ether: ethyl acetate=10:1.
The heating reflux temperature of the step (3) is 100-150 ℃ and the heating time is 0.5-2 hours.
The feeding sequence of the steps is 3, 3-dimethyl-2-ethylindole, 2-formylpyrrole, toluene, triethylamine and boron trifluoride diethyl etherate.
The invention has the following beneficial effects:
(1) The seven-element N, N-fluoboric dye and acrylic resin have high film forming speed on a film, and at low concentration, the seven-element N, N-fluoboric dye and acrylic resin show transparent color when irradiated by natural light, clear yellow fluorescence can be seen under an ultraviolet lamp, the difference between front and back contrast is obvious, the difference is high, and the seven-element N, N-fluoboric dye and acrylic resin can be widely applied to the fields of fluorescence holographic anti-counterfeiting films, fluorescence anti-counterfeiting packaging films and the like.
(2) The method has the advantages of simple synthesis steps, mild reaction conditions, simple purification, low manufacturing cost, high solid fluorescence quantum yield and general applicability.
Drawings
FIG. 1 is a YJ-1FB hydrogen spectrum of the compound obtained in example 1.
FIG. 2 is a carbon spectrum of YJ-1FB of the compound obtained in example 1.
FIG. 3 is a hydrogen spectrum of the compound YJ-2FB obtained in example 2.
FIG. 4 is a carbon spectrum of the compound YJ-2FB obtained in example 2.
FIG. 5 is a hydrogen spectrum of the compound YJ-3FB obtained in example 3.
FIG. 6 is a carbon spectrum of the compound YJ-3FB obtained in example 3.
FIG. 7 is a clear fluorescent chart obtained by photographing the obtained compounds YJ-2FB, YJ-1FB and YJ-3FB with an acrylic resin on a preservative film and an HONOR 20 mobile phone under an ultraviolet lamp of 365nm in order from left to right in example 9.
FIG. 8 is a clear fluorescent image obtained by photographing with an HONOR 20 mobile phone under 365nm ultraviolet light when 5. Mu.L, 10. Mu.L, 15. Mu.L and 20. Mu.L are sequentially arranged from top to bottom in example 10.
In example 10 of FIG. 9, 5. Mu.L, 10. Mu.L, 15. Mu.L and 20. Mu.L were sequentially arranged from top to bottom, and a clear natural light pattern was obtained by photographing with an HONOR 20 mobile phone under natural light.
Detailed Description
The present invention will be further illustrated by the following examples, but the scope of the invention is not limited to the examples.
Example 1
3, 3-dimethyl-2-ethylindole (173 mg,1.0 mmol) and 2-formylpyrrole (47.5 mg,0.5 mmol) were weighed and heated to reflux at 120℃in 16ml of toluene, and piperidine (100. Mu.l, 1.0 mmol) and acetic acid (60. Mu.l, 1.0 mmol) were added thereto to react for 4 hours. TLC plates were monitored and after completion of the reaction, triethylamine (1 ml,7.2 mmol) was added thereto, boron trifluoride etherate (1 ml,8 mmol) was heated under reflux for 0.5h. And monitoring a TLC (thin layer chromatography) plate, washing a product after the reaction is finished, extracting, drying, separating and purifying by column chromatography, and performing rotary evaporation to obtain solid products YJ-1FB, YJ-2FB and YJ-3FB with the yields of 11.4%, 14.2% and 5.3% respectively.
Example 2
3, 3-dimethyl-2-ethylindole (173 mg,1.0 mmol) and 2-formylpyrrole (95 mg,1 mmol) were weighed and heated to reflux at 120℃in 16ml of toluene, and piperidine (100. Mu.l, 1.0 mmol) and acetic acid (60. Mu.l, 1.0 mmol) were added thereto to react for 4 hours. TLC plates were monitored and after completion of the reaction, triethylamine (1 ml,7.2 mmol) was added thereto, boron trifluoride etherate (1 ml,8 mmol) was heated under reflux for 0.5h. And monitoring a TLC (thin layer chromatography) plate, washing a product after the reaction is finished, extracting, drying, separating and purifying by column chromatography, and performing rotary evaporation to obtain solid products YJ-1FB, YJ-2FB and YJ-3FB with the yields of 17.4%, 15.2% and 18% respectively.
When the amount of 2-formylpyrrole was increased 1-fold relative to example 1, the YJ-1FB yield was increased by 6%, the YJ-2FB yield was increased by 1%, and the YJ-3FB yield was increased by 12.7%.
Example 3
3, 3-dimethyl-2-ethylindole (173 mg,1.0 mmol) and 2-formylpyrrole (142.5 mg,1.5 mmol) were weighed and heated to reflux at 120℃in 16ml of toluene, and piperidine (100. Mu.l, 1.0 mmol) and acetic acid (60. Mu.l, 1.0 mmol) were added thereto to react for 4 hours. TLC plates were monitored and after completion of the reaction, triethylamine (1 ml,7.2 mmol) was added thereto, boron trifluoride etherate (1 ml,8 mmol) was heated under reflux for 0.5h. And monitoring a TLC (thin layer chromatography) plate, washing a product after the reaction is finished, extracting, drying, separating and purifying by column chromatography, and performing rotary evaporation to obtain solid products YJ-1FB, YJ-2FB and YJ-3FB with the yields of 13.5%, 15.2% and 17.1% respectively.
When the amount of 2-formylpyrrole was increased 1.5 times relative to example 1, the YJ-1FB yield was increased by 2.1%, the YJ-2FB yield was increased by 1%, and the YJ-3FB yield was increased by 11.8%.
Example 4
3, 3-dimethyl-2-ethylindole (173 mg,1.0 mmol) and 2-formylpyrrole (190 mg,2 mmol) were weighed and heated to reflux at 120℃in 16ml of toluene, and piperidine (100. Mu.l, 1.0 mmol) and acetic acid (60. Mu.l, 1.0 mmol) were added thereto to react for 4 hours. TLC plates were monitored and after completion of the reaction, triethylamine (1 ml,7.2 mmol) was added thereto, boron trifluoride etherate (1 ml,8 mmol) was heated under reflux for 0.5h. And monitoring a TLC (thin layer chromatography) plate, washing a product after the reaction is finished, extracting, drying, separating and purifying by column chromatography, and performing rotary evaporation to obtain solid products YJ-1FB, YJ-2FB and YJ-3FB with the yields of 13.6%, 12.7% and 16.5% respectively.
When the amount of 2-formylpyrrole was increased 2-fold relative to example 1, the YJ-1FB yield was reduced by 3.8%, the YJ-2FB yield was reduced by 2.5%, and the YJ-3FB yield was reduced by 1.5%.
Example 5
3, 3-dimethyl-2-ethylindole (173 mg,1.0 mmol) and 2-formylpyrrole (47.5 mg,0.5 mmol) were weighed and heated to reflux at 120℃in 16ml of toluene, and piperidine (100. Mu.l, 1.0 mmol) and acetic acid (60. Mu.l, 1.0 mmol) were added thereto to react for 4 hours. After completion of the reaction, triethylamine (0.5 ml,3.6 mmol) was added thereto and boron trifluoride etherate (0.5 ml,4 mmol) was refluxed for 0.5h. And monitoring a TLC (thin layer chromatography) plate, washing a product after the reaction is finished, extracting, drying, separating and purifying by column chromatography, and performing rotary evaporation to obtain solid products YJ-1FB, YJ-2FB and YJ-3FB with the yields of 9.7%, 12.1% and 1.7% respectively.
When the amounts of triethylamine, boron trifluoride etherate solution were reduced by half relative to example 1, the yields of YJ-1FB, YJ-2FB, YJ-3FB were reduced by 1.7%, 2.1%, 3.6%, respectively.
Example 6
3, 3-dimethyl-2-ethylindole (173 mg,1.0 mmol) and 2-formylpyrrole (47.5 mg,0.5 mmol) were weighed and heated to reflux at 120℃in 16ml of toluene, and piperidine (100. Mu.l, 1.0 mmol) and acetic acid (60. Mu.l, 1.0 mmol) were added thereto to react for 4 hours. TLC plates were monitored and after completion of the reaction, triethylamine (2 ml,14.4 mmol) was added thereto, boron trifluoride etherate (2 ml,16 mmol) was heated at reflux for 0.5h. And monitoring a TLC (thin layer chromatography) plate, washing a product after the reaction is finished, extracting, drying, separating and purifying by column chromatography, and performing rotary evaporation to obtain solid products YJ-1FB, YJ-2FB and YJ-3FB with the yields of 11.9%, 14.1% and 5.1% respectively.
When the amounts of triethylamine and boron trifluoride etherate were doubled relative to example 1, the yields of YJ-1FB, YJ-2FB and YJ-3FB were increased by 0.5%, 0.1% and 0.2%, respectively.
Example 7
3, 3-dimethyl-2-ethylindole (173 mg,1.0 mmol) and 2-formylpyrrole (47.5 mg,0.5 mmol) were weighed and heated to reflux at 90℃in 16ml of toluene, and piperidine (100. Mu.l, 1.0 mmol) and acetic acid (60. Mu.l, 1.0 mmol) were added thereto to react for 4 hours. TLC plates were monitored and after completion of the reaction, triethylamine (1 ml,7.2 mmol) was added thereto, boron trifluoride etherate (1 ml,8 mmol) was heated under reflux for 0.5h. And monitoring a TLC (thin layer chromatography) plate, washing a product after the reaction is finished, extracting, drying, separating and purifying by column chromatography, and performing rotary evaporation to obtain solid products YJ-1FB, YJ-2FB and YJ-3FB with the yields of 7.3%, 8.1% and 1.7% respectively.
When the reaction temperature was lowered by 30℃relative to example 1, the yields of YJ-1FB, YJ-2FB and YJ-3FB were lowered by 4.1%, 6.1% and 3.4%, respectively.
Example 8
3, 3-dimethyl-2-ethylindole (173 mg,1.0 mmol) and 2-formylpyrrole (47.5 mg,0.5 mmol) were weighed and heated to reflux at 150℃in 16ml of toluene, and piperidine (100. Mu.l, 1.0 mmol) and acetic acid (60. Mu.l, 1.0 mmol) were added thereto to react for 4 hours. TLC plates were monitored and after completion of the reaction, triethylamine (1 ml,7.2 mmol) was added thereto, boron trifluoride etherate (1 ml,8 mmol) was heated under reflux for 0.5h. And monitoring a TLC (thin layer chromatography) plate, washing a product after the reaction is finished, extracting, drying, separating and purifying by column chromatography, and performing rotary evaporation to obtain solid products YJ-1FB, YJ-2FB and YJ-3FB with the yields of 9.7%, 11.1% and 3.9% respectively.
When the reaction temperature was increased by 30℃relative to example 1, the yields of YJ-1FB, YJ-2FB and YJ-3FB were decreased by 1.7%, 2.8% and 1.4%, respectively.
Example 9
The four compounds YJ-1FB (2.98 mg,0.01 mmol), YJ-2FB (2.98 mg,0.01 mmol) and YJ-3FB (3.75 mg,0.01 mmol) were weighed, dissolved with 1mL of dichloromethane to prepare 0.01mol/L mother liquor, 3. Mu.L of mother liquor was dissolved in 20. Mu.L of acrylic resin, and the mixture was uniformly coated on a preservative film, dried at 36℃and then the preservative film was placed under an ultraviolet lamp (365 nm) and photographed with a HONOR 20 mobile phone to obtain a clear fluorescent pattern, as shown in FIG. 7.
It can be observed that the solid fluorescent intensity of the compound YJ-1FB is strongest, and therefore, the compound YJ-1FB is selected as a solid fluorescent dye for subsequent application.
Example 10
Weighing compound YJ-1FB (2.98 mg,0.01 mmol), dissolving 1mL of dichloromethane to prepare mother solution of 0.01mol/L, respectively dissolving 5 mu L, 10 mu L, 15 mu L and 20 mu L of mother solution into 20 mu L of acrylic resin, uniformly coating onto a preservative film, drying at 36 ℃, and placing the preservative film under an ultraviolet lamp (365 nm), photographing by using a HONOR 20 mobile phone to obtain a clear fluorescent diagram, as shown in figure 8. It can be observed that the fluorescence intensity is changed from weak to strong and then weak with the increase of the mother solution amount, and the fluorescence intensity of 10 mu L of the mother solution is the brightest, and the concentration is the most suitable for the preparation of the anti-counterfeiting film. FIG. 8 shows clear fluorescent patterns obtained by dissolving the compound YJ-1FB obtained in example 10 in methylene chloride to prepare a mother solution, dissolving 5. Mu.L, 10. Mu.L, 15. Mu.L and 20. Mu.L of the mother solution in 20. Mu.L of an acrylic resin and forming a film on a fresh keeping film, and photographing the film with an HONOR 20 mobile phone under an ultraviolet lamp (365 nm). FIG. 9 is a diagram showing clear natural light patterns obtained by dissolving the compound YJ-1FB obtained in example 10 in methylene chloride to prepare a mother solution, dissolving 5. Mu.L, 10. Mu.L, 15. Mu.L and 20. Mu.L of the mother solution in 20. Mu.L of an acrylic resin and forming a film on a preservative film, and photographing with an HONOR 20 mobile phone under natural light. From the figure, the natural light intensity is optimal when the amount of the mother solution is 10 mu L, which is beneficial to the preparation of the anti-counterfeiting film.

Claims (10)

  1. BODIPY solid fluorescent dye, which is characterized in that the chemical structural formulas of the fluorescent dye are respectively as follows:
  2. 2. the method for preparing the BODIPY solid fluorescent dye according to claim 1, wherein the method comprises the following steps:
    the method comprises the following steps:
    (1) Adding 3, 3-dimethyl-2-ethylindole, 2-formylpyrrole and solvent toluene into a reaction bottle at room temperature, heating and refluxing, adding catalyst piperidine and acetic acid, and monitoring by TLC to obtain a reaction liquid 1;
    (2) Adding triethylamine into the reaction liquid 1 in the step (1), heating and refluxing with boron trifluoride diethyl etherate, and monitoring by TLC to obtain a reaction liquid 2;
    (3) Washing the reaction liquid 2 in the step (2) respectively, extracting with an extractant, drying, purifying with a column chromatography eluent, and rotary steaming to obtain a solid product YJ-1FBYJ-2FB/>YJ-3FB/>
  3. 3. The method of claim 2, wherein in step (1), 3-dimethyl-2-ethylindole: 2-formylpyrrole: piperidine: the feeding mole ratio of the acetic acid is 1:1-10:0.5-3:0.5-3.
  4. 4. The method of claim 2, wherein the heating reflux temperature in step (1) is 100 to 150 ℃ and the heating time is 1 to 6 hours.
  5. 5. The method according to claim 2, wherein the feeding sequence is 3, 3-dimethyl-2-ethylindole, 2-formylpyrrole, toluene, triethylamine, boron trifluoride etherate.
  6. 6. The method of claim 2, wherein the heating reflux temperature in step (2) is 100 to 150 ℃ and the heating time is 0.5 to 2 hours.
  7. 7. The method of claim 2, wherein the extractant of step (2) is methylene chloride: petroleum ether=1:1, YJ-1FB is eluted from column chromatography eluent petroleum ether: dichloromethane = 2:1, YJ-2FB, YJ-3FB from eluent petroleum ether: ethyl acetate=10:1.
  8. 8. A BODIPY fluorescent material, characterized in that the material is any one of the fluorescent materials prepared according to claim 1 or claims 2-7.
  9. 9. The BODIPY fluorescent material according to claim 8, wherein the BODIPY fluorescent material is a fluorescent anti-counterfeiting material, does not exhibit fluorescence upon sunlight irradiation, and achieves yellow fluorescence upon 365nm ultraviolet light irradiation.
  10. 10. The BODIPY fluorescent material of claim 8, wherein the use of the BODIPY fluorescent material in a fluorescent holographic anti-counterfeit film.
CN202311351468.0A 2023-10-18 2023-10-18 Preparation and application of seven-membered N, N heterocyclic compound Pending CN117510523A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN202311351468.0A CN117510523A (en) 2023-10-18 2023-10-18 Preparation and application of seven-membered N, N heterocyclic compound

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN202311351468.0A CN117510523A (en) 2023-10-18 2023-10-18 Preparation and application of seven-membered N, N heterocyclic compound

Publications (1)

Publication Number Publication Date
CN117510523A true CN117510523A (en) 2024-02-06

Family

ID=89759670

Family Applications (1)

Application Number Title Priority Date Filing Date
CN202311351468.0A Pending CN117510523A (en) 2023-10-18 2023-10-18 Preparation and application of seven-membered N, N heterocyclic compound

Country Status (1)

Country Link
CN (1) CN117510523A (en)

Similar Documents

Publication Publication Date Title
CN110218220B (en) Functionalized metal-organic framework compound, complex formed by functionalized metal-organic framework compound, and preparation method and application of functionalized metal-organic framework compound
CN110461820B (en) Organic luminophores
CN112679518B (en) Pure organic room temperature phosphorescent material based on thiochromanone derivative and preparation method and application thereof
CN111440193B (en) Indene-thick naphtho-spirooxazine photochromic compound and preparation method thereof
US5320784A (en) Crystal comprising an indolinospirobenzothiopyran derivative and its ring opened isomer
CN113185524B (en) Six-membered spiro rhodamine photochromic fluorescent dye containing urea structure as well as preparation method and application thereof
CN110117235B (en) Compound with aggregation-induced light emission and mechanochromism characteristics and preparation method and application thereof
CN117510523A (en) Preparation and application of seven-membered N, N heterocyclic compound
CN113896736B (en) Aryl-substituted spirooxazine photochromic compound and preparation method and application thereof
CN110551292A (en) preparation method of rare earth luminescent material with adjustable light color
CN111471455B (en) Preparation method and application of acetophenone and derivative-substituted thiazolyl viologen high-fluorescence photochromic material
CN115745875A (en) Light-operated organic electroluminescent material containing triphenylethylene group, and synthesis method and application thereof
CN110041226B (en) Compound with AIE characteristics and preparation method and application thereof
CN113087732A (en) BODIPY solid fluorescent dye and application thereof to fluorescent holographic anti-counterfeiting highlight film
CN110669065B (en) Axial chirality binaphthol-boron dipyrrole-based complex and preparation method thereof
CN112939998A (en) Spiropyran derivative, photochromic material and preparation method thereof
CN1255412C (en) 6'-heterocycle substituted spirooxazine photochromic compound and method for preparing same
CN114605453B (en) BODIPY fluorescent toner with AIE effect and application thereof in fluorescent anti-counterfeiting film
CN111518120A (en) Synthetic method for improving photochromic property of spiropyran by introducing multi-aromatic ring
CN108558595B (en) P-phenylene ethylene bridged trimer indene derivative and preparation method thereof
CN111909186A (en) Preparation method of red fluorescent material
CN115448936A (en) N, O-heterocyclic compound and synthesis and application thereof
CN115286650A (en) Preparation and application of seven-membered N, O heterocyclic compound
CN115340556B (en) Preparation method and application of pyrrolizine compounds
CN114685381B (en) Donor-acceptor Stenhaus adduct of non-conjugated aniline bridged tetraphenyl ethylene and preparation method and application thereof

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination