CN112442054A - Preparation method of trimeric indenyl corrole-porphyrin-BODIPY star-shaped compound - Google Patents
Preparation method of trimeric indenyl corrole-porphyrin-BODIPY star-shaped compound Download PDFInfo
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 33
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 title claims abstract description 25
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 title claims abstract description 21
- 238000002360 preparation method Methods 0.000 title abstract description 8
- 238000000034 method Methods 0.000 claims abstract description 16
- 238000006243 chemical reaction Methods 0.000 claims abstract description 9
- -1 indenyl corrole derivative Chemical class 0.000 claims abstract description 8
- 239000003054 catalyst Substances 0.000 claims abstract description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract 5
- 238000006069 Suzuki reaction reaction Methods 0.000 claims abstract 2
- 229910052763 palladium Inorganic materials 0.000 claims abstract 2
- 150000004033 porphyrin derivatives Chemical class 0.000 claims abstract 2
- 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 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- 238000005829 trimerization reaction Methods 0.000 claims description 9
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 8
- YGPLLMPPZRUGTJ-UHFFFAOYSA-N truxene Chemical compound C1C2=CC=CC=C2C(C2=C3C4=CC=CC=C4C2)=C1C1=C3CC2=CC=CC=C21 YGPLLMPPZRUGTJ-UHFFFAOYSA-N 0.000 claims description 6
- 238000010898 silica gel chromatography Methods 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 229910052786 argon Inorganic materials 0.000 claims description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000000243 solution Substances 0.000 claims description 3
- 238000006555 catalytic reaction Methods 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- 238000001704 evaporation Methods 0.000 claims description 2
- 239000011259 mixed solution Substances 0.000 claims description 2
- 238000000746 purification Methods 0.000 claims description 2
- 239000002994 raw material Substances 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- QQVHHGYRLLIYNR-UHFFFAOYSA-N C1=CC=C2C3=CC=CC=C3NC2=C1.N1C(C=C2N=C(C=C3NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1.N1C(C=C2N=C(C=C3NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 QQVHHGYRLLIYNR-UHFFFAOYSA-N 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 230000031700 light absorption Effects 0.000 abstract description 6
- 238000010672 photosynthesis Methods 0.000 abstract description 4
- 230000029553 photosynthesis Effects 0.000 abstract description 4
- 238000004088 simulation Methods 0.000 abstract description 3
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 238000012546 transfer Methods 0.000 description 6
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- LYNARWYQOUZXDY-UHFFFAOYSA-N corrole Chemical compound N1C(C=C2NC(=CC=3NC4=CC=3)C=C2)=CC=C1C=C1C=CC4=N1 LYNARWYQOUZXDY-UHFFFAOYSA-N 0.000 description 3
- 238000013461 design Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000002189 fluorescence spectrum Methods 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 150000004032 porphyrins Chemical class 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 230000027756 respiratory electron transport chain Effects 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- LNNZFLUZEQJWPS-UHFFFAOYSA-N C1(=CC=CC=2C3=CC=CC=C3NC12)C1C=CC2=CC=CC=C12 Chemical compound C1(=CC=CC=2C3=CC=CC=C3NC12)C1C=CC2=CC=CC=C12 LNNZFLUZEQJWPS-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000004577 artificial photosynthesis Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 229910003472 fullerene Inorganic materials 0.000 description 1
- 150000002678 macrocyclic compounds Chemical class 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000000877 morphologic effect Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000033116 oxidation-reduction process Effects 0.000 description 1
- 238000006552 photochemical reaction Methods 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
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- 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
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—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
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- C—CHEMISTRY; METALLURGY
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- 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
- C09K2211/1074—Heterocyclic compounds characterised by ligands containing more than three nitrogen atoms as heteroatoms
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Abstract
The invention discloses a structure of trimeric indenyl corrole-porphyrin-BODIPY star-shaped compound shown in formula (I) and a preparation method thereof. The method is realized by the following steps: the trimeric indenyl corrole derivative shown in the formula (II) reacts with the porphyrin derivative shown in the formula (III) under the action of a palladium catalyst to obtain a ternary system compound shown in the formula (IV); then carrying out Suzuki coupling reaction with the BODIPY derivative shown in the formula (V) to obtain the trimeric indenyl corrole-porphyrin-BODIPY star compound shown in the formula (I). The star-shaped compound has the advantages of simple preparation method, mild reaction conditions, simple and convenient operation, strong light absorption capacity and fluorescence intensity, and can be used for light absorption antennas, solar cells, artificial simulation of photosynthesis and the like.
Description
Technical Field
The invention belongs to the technical field of organic synthesis, and relates to a preparation method of a star-shaped compound based on truxene.
Background
Photoinduced energy/electron transfer plays an important role in photochemical reactions, solar energy utilization, photosynthesis mechanisms and the like. The application and research of molecular structure models based on light-induced energy/electron transfer mechanism in the aspects of optical molecular devices, solar cells, artificial photosynthesis and the like has become a very active research field at home and abroad. Dye molecules with electron/energy donor-acceptor performance have shown wide application prospects in the aspect of organic photoelectric functional materials. However, the star-shaped compound with the donor-acceptor structure still has the defects of multiple synthesis steps, complex reaction, low yield and the like, so that the design and synthesis of the novel star-shaped compound which has good energy/electron transfer process and is easy to synthesize is of great significance.
In molecular models with different structure types, the unique three-dimensional star-emitter structure of the star-shaped compound is beneficial to regulating and controlling the photoelectric property and morphological characteristics of molecules, and a plurality of outwardly extending support arms can improve the charge transfer or energy transfer efficiency and have been widely concerned. The truxene (truxene) has a large rigid conjugated structure, is a three-fold symmetric plane rigid condensed ring aromatic hydrocarbon, is favorable for intramolecular charge transfer, is easy to perform functional design and modification at the 2, 7 and 12 positions of three end groups, and has been proved to be one of ideal compounds for preparing star-shaped compounds. Porphyrin and Corrole (core) are macrocyclic compounds formed by conjugation of 4 pyrroles, have excellent physicochemical properties, are excellent photoelectric functional material molecules, and show wide application prospects in the design and synthesis of energy/electron donor or acceptor molecular systems. The BODIPY fluorescent dye has the advantages of high molar absorption coefficient, high fluorescence quantum yield, insensitivity of a fluorescence signal to solvent polarity and pH, narrow fluorescence spectrum peak, long fluorescence life, moderate oxidation-reduction potential, negligible triplet state and the like, and is also an excellent photoelectric functional material molecule. Therefore, different photoactive groups such as porphyrin, BODIPY, corrole and the like can be grafted on three end groups of 2, 7 and 12 of the truxene respectively through a simple chemical synthesis method to form the long-life charge separation state donor/acceptor star-shaped compound with efficient energy transfer and charge transfer, and the compound can be widely applied to application research in the aspects of light absorption antennas, solar cells, artificial simulation photosynthesis and the like.
Disclosure of Invention
The purpose of the invention is as follows: aiming at the defects in the prior art, the invention aims to provide a preparation method of a trimerization indenyl corrole-porphyrin-BODIPY star-shaped compound.
The technical scheme is as follows: in order to achieve the purpose of the invention, the invention adopts the technical scheme that:
the trimeric indenyl corrole-porphyrin-BODIPY star-shaped compound related by the invention has the following structure:
the synthetic route of the trimeric indenyl corrole-porphyrin-BODIPY star-shaped compound related by the invention is as follows:
the preparation process of the trimeric indenyl corrole-porphyrin-fullerene star-shaped compound comprises the following steps:
step 1: under the protection of argon, dissolving the trimeric indenyl corrole derivative shown in the formula (II) and the meso-phenyl borate porphyrin derivative shown in the formula (III) in tetrahydrofuran, adding a mixed solution of anhydrous potassium carbonate, water and methanol in a certain proportion into a reactor, finally adding a catalyst of tetrakis (triphenylphosphine) palladium, reacting at 75-85 ℃ for 12 hours, cooling to room temperature after the reaction is finished, adding a saturated ammonium chloride solution, extracting with dichloromethane, evaporating to dryness, and separating and purifying by silica gel column chromatography to obtain a trimeric indenyl corrole-porphyrin intermediate shown in the formula (IV);
step 2: according to the same method of the step 1, the trimerization indenyl corrole-porphyrin intermediate shown in the formula (IV) reacts with the meso-phenyl borate BODIPY derivative shown in the formula (V) under the catalysis of tetrakis (triphenylphosphine) palladium, and the trimerization indenyl corrole-porphyrin-BODIPY ternary system compound shown in the formula (I) is obtained through silica gel column chromatography separation and purification;
4. the production method according to claim 3, wherein the amount of the substance of the trimeric indenylaldehydic corrole derivative of formula ((II) and the meso-phenyl boronate porphyrin derivative of formula (III) in the step 1 is 1: 1;
5. the method according to claim 3, wherein in the step 2, the ratio of the amounts of the trimeric indenyl corrole-porphyrin intermediate represented by the formula (IV) and the meso-phenyl boronate BODIPY biological substance represented by the formula (V) is 1: 1.2;
6. the method according to claim 3, wherein in the steps 1 and 2, the amount of the catalyst tetrakis (triphenylphosphine) palladium is 20% of the amount of the reactant raw material;
the invention has the advantages of
Compared with the prior art, the preparation method of the trimeric indenyl star compound has the advantages that: (1) three different photoactive groups of carbazole, porphyrin and 8ODIPY are respectively introduced into three active positions of truxene 2, 7 and 12 to form a star-shaped molecular system of energy donor-energy acceptor and electron donor-electron acceptor, the electron/energy transfer process can be continuously generated for multiple times in the same molecule, the light absorption range is wide, and the light absorption antenna can be used as a light absorption antenna and an artificial simulation biological photosynthesis process. (2) The method has the advantages of simple synthetic route, mild reaction conditions, good reaction selectivity, simple separation method and universality, and can be popularized and applied to the synthesis of a trimeric indenyl-based star-shaped compound.
Drawings
FIG. 1 is a UV-VIS absorption spectrum of Compound II of the present invention;
FIG. 2 is a UV-VIS absorption spectrum of Compound III of the present invention;
FIG. 3 is a UV-VIS absorption spectrum of Compound V of the present invention;
FIG. 4 is a UV-VIS absorption spectrum of Compound I of the present invention;
FIG. 5 shows fluorescence emission spectra of compounds of formulae II, III, V, and I.
Detailed Description
The present invention is further explained below with reference to specific examples, which are not intended to limit the present invention in any way.
By using1H-NMR, ultraviolet-visible and fluorescence spectra characterize the structure of the compound and investigate the photophysical properties of the compound. The detection instrument is as follows: brukerarx500 nuclear magnetismA resonance instrument (TMS is an internal standard and deuterated chloroform is a solvent), an Shimadzu UV-3100 type ultraviolet-visible spectrophotometer (the scanning range is 400-800 nm and the light path slit is 2nm), a PE LS-55 type fluorescence spectrophotometer (the wavelength range is 200 nm for exciting light and 800nm and 900nm for emitting light, and the slit is variable, 2.5-15nm for exciting light path, 2.5-20nm for emitting light path and 0.1nm for step pitch).
Example 1
Adding 7, 12-dibromo truxene carbazole derivative (II) (0.12mmol, 155.9mg), meso-phenyl boronate porphyrin derivative (III) (0.1mmol, 96.3mg) and anhydrous potassium carbonate (10mmol, 138.0mg) into a reactor, adding dried tetrahydrofuran (40mL), adding methanol and water (v/v, 2.5mL/2.5mL) according to the proportion, finally adding tetrakis (triphenylphosphine) palladium (0.01mmol, 12.0mg), heating to 75-85 ℃ under argon condition, reacting for 12 hours, extracting an organic layer after the reaction is finished, washing the organic layer with dichloromethane solution, drying with anhydrous sodium sulfate, spin-drying a solvent, and purifying by silica gel column chromatography (dichloromethane-petroleum ether is used as an eluent) to obtain the trimeric indenyl carbazole Intermediate (IV) which is 51mg (yield is 25%).1H NMR：(600MHz，CDCl3)δppm 9.16(s，4H)，9.01-8.76(m，12H)，8.62(s，4H)，8.38(dd，J＝11.13，7.85Hz，4H)，8.25(s，4H)，8.15-8.01(m，2H)，7.73-7.35(m，4H)，3.50-3.08(m，6H)，2.57-2.28(m，6H)，0.66-0.41(m，18H)，-2.77(d，J＝4.01Hz，2H)。
Example 2
Adding 0.02mmol and 41.2mg of the Intermediate (IV) of the trimerization indenyl carbazole-porphyrin and 0.025mmol and 17.2mg of the meso-phenyl borate BODIPY derivative (V) into a reactor, dissolving the Intermediate (IV) of the trimerization indenyl carbazole-porphyrin and the meso-phenyl borate BODIPY derivative (V) in tetrahydrofuran (20mL), weighing anhydrous potassium carbonate (2mmol and 27.6mg), adding water and methanol (1mL/1mL) according to the proportion, adding 0.005mmol and 6.0mg of tetrakis (triphenylphosphine) palladium into the reaction under the argon condition, heating to 75-85 ℃, reacting for 12 hours, extracting an organic phase by using dichloromethane and washing by using a saturated ammonium chloride aqueous solution after the reaction is finished, drying the organic layer by using anhydrous sodium sulfate, decompressing and rotating the solvent, and carrying out chromatographic separation and purification by using dichloromethane-petroleum ether as an eluent to obtain the trimerization indenyl carbazole-BODIPY ternary systemization of the trimerization indenyl carbazole-porphyrin and the meso-BODIPYCompound (I) was 17mg (33% yield).1H NMR：(600MHz，CDCl3)δppm 9.23-9.07(m，4H)，8.91(d，J＝5.35Hz，12H)，8.77-8.55(m，4H)，8.40-8.36(m，2H)，8.34-8.18(m，4H)，8.18-8.07(m，2H)，8.01-7.96(m，2H)，7.96-7.88(m，2H)，7.60(d，J＝8.78Hz，12H)，7.42-7.36(m，1H)，7.25-7.22(m，1H)，6.94(d，J＝8.57Hz，4H)，6.68(s，2H)，3.86(d，J＝5.07Hz，6H)，3.52-3.20(m，6H)，2.62-2.42(m，6H)，1.29(dd，J＝10.61，7.16Hz，15H)，0.68-0.49(m，18H)，-2.74(m，2H)。
Claims (7)
1. A trimeric indenyl corrole-porphyrin-BODIPY star compound shown as a formula (I):
2. a method for preparing trimeric indenyl corrole-porphyrin-BODIPY star-shaped compound shown in formula (I) as patent claim 1, which is characterized in that the method comprises the following steps: the trimeric indenyl corrole derivative shown in the formula (II) and the porphyrin derivative shown in the formula (III) react under the action of a palladium catalyst to obtain a trimeric indenyl-corrole-porphyrin ternary system compound shown in the formula (IV); finally, carrying out Suzuki coupling reaction on the ternary system compound shown in the formula (IV) and the BODIPY derivative shown in the formula (V) to obtain a trimeric indenyl corrole-porphyrin-BODIPY star-shaped compound shown in the formula (I);
3. the method of claim 2, wherein the method comprises the steps of:
step 1: under the protection of argon, dissolving a truxene carbazole derivative shown in a formula (II) and a meso-phenyl borate porphyrin derivative shown in a formula (III) in tetrahydrofuran, adding a mixed solution of anhydrous potassium carbonate and water and methanol in a certain proportion into a reactor, finally adding a catalyst of tetrakis (triphenylphosphine) palladium, reacting at 75-85 ℃ for 12 hours, cooling to room temperature after the reaction is finished, adding a saturated ammonium chloride solution, extracting and separating with dichloromethane, evaporating an organic solvent, and separating and purifying by silica gel column chromatography to obtain a truxene carbazole-porphyrin intermediate shown in a formula (IV);
step 2: according to the same method of the step 1, the trimerization indenyl corrole-porphyrin intermediate shown in the formula (IV) reacts with the meso-phenyl borate BODIPY derivative shown in the formula (V) under the catalysis of tetrakis (triphenylphosphine) palladium, and the trimerization indenyl corrole-porphyrin-BODIPY ternary system compound shown in the formula (I) is obtained through silica gel column chromatography separation and purification.
4. The production method according to claim 3, wherein the amount of the substance of the trimeric indenyl corrole derivative represented by the formula ((II) and the meso-phenyl boronate porphyrin derivative represented by the formula (III) in the step 1 is 1.2: 1.
5. The method according to claim 3, wherein in the step 2, the ratio of the amounts of the trimeric indenyl corrole-porphyrin ternary system compound represented by the formula (IV) and the meso-phenyl boronate BODIPY biological substance represented by the formula (V) is 1: 1.25.
6. The production method according to claim 3, wherein in the steps 1 and 2, tetrakis (triphenylphosphine) palladium (Pd (PPh) is used as a catalyst3)4) The using amount of the catalyst is 10-20% of the amount of the reactant raw material substances.
7. The method according to claim 3, wherein the volume ratio of methanol to water in the steps 1 and 2 is 1: 1.
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| WO2022215541A1 (en) * | 2021-04-09 | 2022-10-13 | 東レ株式会社 | Compound, light-emitting element material, light-emitting element using same, photoelectric conversion material, and photoelectric conversion element using same |
| CN115232161A (en) * | 2022-08-31 | 2022-10-25 | 南京林业大学 | Trihydroindenyl-BODIPY-perylene diimide ternary system molecule and preparation method thereof |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2022215541A1 (en) * | 2021-04-09 | 2022-10-13 | 東レ株式会社 | Compound, light-emitting element material, light-emitting element using same, photoelectric conversion material, and photoelectric conversion element using same |
| CN113402536A (en) * | 2021-06-11 | 2021-09-17 | 南京林业大学 | Porphyrin bridged double BODIPY derivative and preparation method thereof |
| CN113402536B (en) * | 2021-06-11 | 2022-04-19 | 南京林业大学 | Porphyrin bridged double BODIPY derivative and preparation method thereof |
| CN115232161A (en) * | 2022-08-31 | 2022-10-25 | 南京林业大学 | Trihydroindenyl-BODIPY-perylene diimide ternary system molecule and preparation method thereof |
| CN115232161B (en) * | 2022-08-31 | 2024-07-02 | 南京林业大学 | Trimerdanyl-BODIPY-perylene diimide ternary system molecule and preparation method thereof |
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