CN105949205A - Nitrogen-atom-doped condensed-nucleus aromatic hydrocarbon compounds as well as preparation method and application thereof - Google Patents

Nitrogen-atom-doped condensed-nucleus aromatic hydrocarbon compounds as well as preparation method and application thereof Download PDF

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CN105949205A
CN105949205A CN201610309809.1A CN201610309809A CN105949205A CN 105949205 A CN105949205 A CN 105949205A CN 201610309809 A CN201610309809 A CN 201610309809A CN 105949205 A CN105949205 A CN 105949205A
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condensed
reaction
nuclei aromatics
compound
nitrogen atom
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赖文勇
成程
黄维
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Nanjing Post and Telecommunication University
Nanjing University of Posts and Telecommunications
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Nanjing Post and Telecommunication University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
    • C07D487/14—Ortho-condensed systems
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole

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  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Indole Compounds (AREA)

Abstract

The invention provides nitrogen-atom-doped condensed-nucleus aromatic hydrocarbon compounds as well as a preparation method and an application thereof. More specifically, a hexabromo-tricarbarzole derivative (TATBr) and 2-arylboronic acid are subjected to a microwave-assisted Suzuki coupling reaction, and a hexaaryl-tricarbarzole derivative is obtained, and then the nitrogen-atom-doped condensed-nucleus aromatic hydrocarbon compounds based on tricarbarzole as nuclei and obtained through step-by-step dehydrogenation are obtained through oxidative dehydrogenation and cyclization reactions with ferric trichloride/nitromethane as an oxidizing agent. The specific general structural formula of the compounds is shown in the specification, wherein Ar is selected from one of groups shown in the specification, R is linear or branched alkyl of C1-C20, and * represents a linkage site. The compounds have the characteristics that purification is easy, the solubility is good, a self-assembly structure is formed easily in a solution, high chemical purity can be obtained with a simple column chromatography method and the like, and can be widely applied to organic photoelectric devices.

Description

A kind of condensed-nuclei aromatics compound of nitrogen atom doping and preparation method and application
Technical field
The invention belongs to photoelectric material and applied technical field, be specifically related to the condensed-nuclei aromatics compound of a kind of nitrogen atom doping And preparation method and application, relate more specifically to a kind of based on three and the condensed ring virtue of nitrogen atom doping that carbazole derivates is core Hydrocarbon compound and preparation method and application.
Background technology
The nano-graphene molecule of condensed-nuclei aromatics class, owing to it has graphene film segment structure feature, increasingly by people Extensive concern.They are widely used in various electronic device, such as organic field effect tube, organic solar batteries With Organic Light Emitting Diode etc..In view of the character of Graphene can carry out Effective Regulation, a series of hetero atoms such as nitrogen by doping (N), boron (B), sulfur (S) are also introduced in condensed-nuclei aromatics compound carrying out a step exploration and improve its performance.With they carbon atoms Analog compare, heteroatomic introducing causes the sp of carbon2Hydridization is destroyed, and this will promote intramolecular charge migration.Meanwhile, Can be by the hetero atom Effective Regulation molecular entergy level introduced and intermolecular interaction.Therefore, the condensed ring of Heteroatom doping Aromatic hydrocarbons has broad application prospects in organic electronic field.
In numerous hetero atoms, nitrogen-atoms is due to the coupling of atom size and its electronegativity so that it becomes replacement carbon One good selection of atom constructing function condensed-nuclei aromatics compound.From the perspective of application, former with band electronegativity nitrogen Son replaces carbon atom can also produce positive effect, and such as the application in Organic Light Emitting Diode, electronegative atom can improve The charge transmission of system.
Although people's condensed-nuclei aromatics substituted to hetero atom is interested.But the synthesis of hetero atom substituted condensed-nuclei aromatics is relatively Relatively difficult, synthetic method is the most little.Therefore, we have proposed by introducing three also carbazole structure primitive as nuclear structure structure The layout strategy of the condensed-nuclei aromatics of nitrogen atom doping, has developed a kind of novelty and has effectively built the side of nitrogen atom doping condensed-nuclei aromatics Method.
Summary of the invention
Technical problem: it is an object of the invention to provide condensed-nuclei aromatics compound and the preparation side thereof of a kind of nitrogen atom doping Method with it in the application of organic electro-optic device.It is to pass through with hexabromo three also carbazole derivates and 2-aryl boric acid for initiation material The Suzuki reaction of microwave-assisted obtains six aryl three carbazole derivates, by ferric chloride/nitromethane system as oxygen Agent carries out oxidative dehydrogenation cyclisation and generates the condensed-nuclei aromatics compound of dehydrocyclization.
Technical scheme: a kind of based on nitrogen atom doping the condensed-nuclei aromatics compound of the present invention with three and carbazole derivates is Nuclear structure, has a general structure as shown in following formula I:
Wherein, Ar is selected from one of following group:
R is the straight or branched alkyl of C1-C20, and * represents link site.
The present invention the synthetic method of condensed-nuclei aromatics compound of nitrogen atom doping be: add hexabromo three under inert atmosphere And carbazole derivates TATBr, tetrabutyl ammonium fluoride, potassium hydroxide, 2-aryl boric acid and tetra-triphenylphosphine palladium be dissolved in solvent, Microwave reactor 100-180 DEG C reaction, reaction after terminating gained crude product separating-purifying is obtained six aryl three and carbazole derives Thing；Gained six aryl three carbazole derivates are dissolved at solvent ,-10-10 DEG C under an inert atmosphere dropping ferric chloride/nitre again Methylmethane oxidation system, is passed through nitrogen bubble reaction, and gained crude product is purified by pillar layer separation, obtains such as reaction expression I The condensed-nuclei aromatics compound of shown nitrogen atom doping.
Wherein:
The preparation method of this condensed-nuclei aromatics compound comprises the following steps:
Step 1: add under an inert atmosphere hexabromo three carbazole, tetrabutyl ammonium fluoride, potassium hydroxide, 2-aryl boric acid and Tetra-triphenylphosphine palladium is also dissolved in solvent orange 2 A, in microwave reactor 100-180 DEG C reaction, through cancellation, washes, extracts, is dried, obtain Crude product separating-purifying；
Step 2: the product of step 1 gained is dissolved in solvent B, at-10-10 DEG C, drips ferric chloride/nitromethane oxygen Change system, is passed through nitrogen bubble reaction；Methanol cancellation, extraction, dried, sucking filtration, obtain crude product, separating-purifying.
Solvent orange 2 A in step 1 is dichloromethane DCM, one in tetrahydrofuran THF, N,N-dimethylformamide DMF or Several, reactant hexabromo three molal quantity of carbazole are 1mmol:2mL～10mL with the volume ratio of solvent orange 2 A, reactant hexabromo three And the molar equivalent of carbazole and tetra-triphenylphosphine palladium is than for 1:5%～10%.
Solvent B in step 2 is dichloromethane DCM, one in tetrahydrofuran THF, N,N-dimethylformamide DMF or Several, the molal quantity of reactions steps 1 product and the volume ratio of solvent B are 1mmol:5mL～15mL, reactions steps 1 product and three The molar equivalent of iron chloride is than for 1:4.0～9.0.
The present invention the condensed-nuclei aromatics compound application in the opto-electronic device of nitrogen atom doping be: described chemical combination owner To be used for building the most surely as the electron transfer layer of the luminescent layer of organic electroluminescence device and organic field effect tube Fixed organic electro-optic device.
Beneficial effect: the condensed-nuclei aromatics compound of the nitrogen atom doping that the present invention proposes has the following characteristics that (1) this chemical combination The cloverleaf pattern structure of thing desirably prevents intermolecular tightly packed, three and carbazole on the replacement of alkyl chain add it often With the dissolubility in solvent；(2) the molecular conjugation degree after condensed ring increases, and improves the charge transport properties of this material；(3) may be used To prepare photoelectric device by easy solution processing mode.Therefore, this compound is a kind of to have having of important application prospect Machine photoelectric functional material.
Accompanying drawing explanation
Fig. 1 is the condensed-nuclei aromatics compound of the nitrogen atom doping of gained ultra-violet absorption spectrum under solution state and fluorescence is sent out Penetrate spectrum.
Detailed description of the invention
A kind of condensed-nuclei aromatics compound of the nitrogen atom doping of the present invention have with three and carbazole as core, substituted aryl is entered The condensed-nuclei aromatics compound that row dehydrocyclization is formed, its formula is as shown in following formula I:
Wherein, Ar is selected from one of following group:
R is the straight or branched alkyl of C1-C20, and * represents link site.
Below by way of some embodiments, the present invention will be further described, but embodiment be not intended to the present invention contain model Enclose.
Embodiment 1:
Target compound TATNaC1
[reaction scheme]
Send out under conditions of four triphenyl phosphorus palladiums make catalyst according to reaction scheme, compound TATBr and 2-naphthalenylboronic acid Raw Suzuki coupling reaction prepares compound TATNa, is slowly added dropwise the ferric chloride dissolved with nitromethane under condition of ice bath Obtain compound TATNaC1.
Suzuki coupling reaction concretely comprises the following steps: under the conditions of lucifuge, in the microwave reaction pipe of 10mL band magnetic stir bar, It is sequentially added into compound TATBr (100mg, 0.074mmol), 2-naphthalenylboronic acid (114mg, 0.66mmol), tetrabutyl ammonium bromide (TBAB) (14.2mg, 0.044mmol) and potassium hydroxide (KOH) (37.6mg, 0.67mmol) are dissolved in 3mL oxolane (THF) In, until completely dissolved, under nitrogen protective condition, add tetra-triphenylphosphine palladium ((Pd (PPh3)4)(51.3mg, 0.044mmol), 150 DEG C of reaction 30min in microwave reactor, reduce temperature to room temperature.Reaction mixture DCM, water is carried out Extraction organic layer, is washed with water repeatedly, merges organic layer, is dried with anhydrous magnesium sulfate, sucking filtration, carries out post layer after concentrated solvent Analysis, obtains white solid 45mg, productivity 45%.
Oxidative dehydrogenation cyclization concretely comprises the following steps: at N2Under protection and lucifuge, by six naphthalenes three carbazoles (102mg, 0.075mmol) add in two mouthfuls of reaction bulbs, add 20mL dichloromethane (DCM) bubbling stand-by.Prepare ferric chloride/nitro first Alkoxide system: by ferric chloride (FeCl3) (48mg, 0.3mmol) add in the distilled nitromethane solution of 1mL, nitrogen Bubbling 15min is stand-by.With syringe, the ferric chloride/nitromethane of preparation is dripped in reaction bulb.Nitrogen bubble reacts 30min.Methanol cancellation is reacted, and with dichloromethane, water carries out extracting organic facies, after deionization washing twice or thrice, and anhydrous magnesium sulfate It is dried, sucking filtration, vacuum-concentrcted crude product, column chromatography purification.Obtain faint yellow solid 30mg, productivity 30%.
Embodiment 2:
Target compound TATNaC2
[reaction scheme]
Send out under conditions of four triphenyl phosphorus palladiums make catalyst according to reaction scheme, compound TATBr and 2-naphthalenylboronic acid Raw Suzuki coupling reaction prepares compound TATNa, is slowly added dropwise the ferric chloride dissolved with nitromethane under condition of ice bath Obtain compound TATNaC2.
Oxidative dehydrogenation cyclization concretely comprises the following steps: at N2Under protection and lucifuge, by six naphthalenes three carbazoles (102mg, 0.075mmol) add in two mouthfuls of reaction bulbs, add 20mL dichloromethane (DCM) bubbling stand-by.Prepare ferric chloride/nitro first Alkoxide system: by ferric chloride (FeCl3) (96mg, 0.6mmol) add in the distilled nitromethane solution of 1mL, nitrogen Bubbling 15min is stand-by.With syringe, the ferric chloride/nitromethane of preparation is dripped in reaction bulb.Nitrogen bubble reacts 30min.Methanol cancellation is reacted, and with dichloromethane, water carries out extracting organic facies, after deionization washing twice or thrice, and anhydrous magnesium sulfate It is dried, sucking filtration, vacuum-concentrcted crude product, column chromatography purification.Obtain faint yellow solid 35mg, productivity 35%.
Embodiment 3:
Target compound TATNaC3
[reaction scheme]
Send out under conditions of four triphenyl phosphorus palladiums make catalyst according to reaction scheme, compound TATBr and 2-naphthalenylboronic acid Raw Suzuki coupling reaction prepares compound TATNa, is slowly added dropwise the ferric chloride dissolved with nitromethane under condition of ice bath Obtain compound TATNaC3.
Oxidative dehydrogenation cyclization concretely comprises the following steps: at N2Under protection and lucifuge, by six naphthalenes three carbazoles (102mg, 0.075mmol) add in two mouthfuls of reaction bulbs, add 20mL dichloromethane (DCM) bubbling stand-by.Prepare ferric chloride/nitro first Alkoxide system: by ferric chloride (FeCl3) (144mg, 0.9mmol) add in the distilled nitromethane solution of 1mL, nitrogen Bubbling 15min is stand-by.With syringe, the ferric chloride/nitromethane of preparation is dripped in reaction bulb.Nitrogen bubble reacts 30min.Methanol cancellation is reacted, and with dichloromethane, water carries out extracting organic facies, after deionization washing twice or thrice, and anhydrous magnesium sulfate It is dried, sucking filtration, vacuum-concentrcted crude product, column chromatography purification.Obtain faint yellow solid 66mg, productivity 65%.
Although we combine exemplary embodiment, it is specifically described the present invention, but those skilled in the art should Work as understanding, in the case of the spirit and scope of the present invention limited without departing from the claims, can be in form with thin Various modifications and alterations are made on joint.

Claims (6)

1. a condensed-nuclei aromatics compound based on nitrogen atom doping, it is characterised in that this compound is with three and carbazole derivates For nuclear structure, there is general structure as shown in following formula I:
Wherein, Ar is selected from one of following group:
R is the straight or branched alkyl of C1-C20, and * represents link site.
2. the synthetic method of the condensed-nuclei aromatics compound of a nitrogen atom doping as claimed in claim 1, it is characterised in that lazy Property atmosphere under add hexabromo three carbazole derivates TATBr, tetrabutyl ammonium fluoride, potassium hydroxide, 2-aryl boric acid and four triphens Base phosphine palladium is also dissolved in solvent, and in microwave reactor 100-180 DEG C reaction, gained crude product separating-purifying is obtained after terminating by reaction Six aryl three carbazole derivates；Again gained six aryl three carbazole derivates are dissolved in solvent ,-10-10 under an inert atmosphere Dripping ferric chloride/nitromethane oxidation system at DEG C, be passed through nitrogen bubble reaction, gained crude product is carried by pillar layer separation Pure, obtain the condensed-nuclei aromatics compound of nitrogen atom doping as shown in reaction expression I.
The synthetic method of the condensed-nuclei aromatics compound of a kind of nitrogen atom doping the most as claimed in claim 2, it is characterised in that should The preparation method of condensed-nuclei aromatics compound comprises the following steps:
Step 1: add hexabromo three carbazole, tetrabutyl ammonium fluoride, potassium hydroxide, 2-aryl boric acid and four or three under an inert atmosphere Phenylphosphine palladium is also dissolved in solvent orange 2 A, in microwave reactor 100-180 DEG C reaction, through cancellation, washes, extracts, is dried, slightly produced Thing separating-purifying；
Step 2: the product of step 1 gained is dissolved in solvent B, at-10-10 DEG C, drips ferric chloride/nitromethane oxysome System, is passed through nitrogen bubble reaction；Methanol cancellation, extraction, dried, sucking filtration, obtain crude product, separating-purifying.
The synthetic method of the condensed-nuclei aromatics compound of a kind of nitrogen atom doping the most as claimed in claim 3, it is characterised in that step Solvent orange 2 A in rapid 1 is dichloromethane DCM, one or more in tetrahydrofuran THF, DMF DMF, reaction Thing hexabromo three molal quantity of carbazole are 1mmol:2mL～10mL with the volume ratio of solvent orange 2 A, reactant hexabromo three carbazole and four The molar equivalent of triphenylphosphine palladium is than for 1:5%～10%.
The synthetic method of the condensed-nuclei aromatics compound of a kind of nitrogen atom doping the most as claimed in claim 3, it is characterised in that step Solvent B in rapid 2 is dichloromethane DCM, one or more in tetrahydrofuran THF, DMF DMF, reaction The molal quantity of step 1 product is 1mmol:5mL～15mL with the volume ratio of solvent B, and reactions steps 1 product rubs with ferric chloride Your equivalent proportion is 1:4.0～9.0.
6. the condensed-nuclei aromatics compound of a nitrogen atom doping as claimed in claim 1 application in the opto-electronic device, it is special Levying and be, described compound passes mainly as the luminescent layer of organic electroluminescence device and the electronics of organic field effect tube Defeated layer is for building the organic electro-optic device of efficient stable.
CN201610309809.1A 2016-05-11 2016-05-11 Nitrogen-atom-doped condensed-nucleus aromatic hydrocarbon compounds as well as preparation method and application thereof Pending CN105949205A (en)

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CN107445968A (en) * 2017-06-14 2017-12-08 南京邮电大学 A kind of two indoles and three and the more arm configuration conjugated molecular materials of carbazyl and preparation method and application
CN113861113A (en) * 2021-09-14 2021-12-31 中国科学院福建物质结构研究所 Preparation and application of fused ring pyridine compound and derivative thereof
CN118185506A (en) * 2024-05-20 2024-06-14 常州威斯敦粘合材料有限责任公司 Efficient UV-converted photovoltaic adhesive film and preparation method thereof

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107445968A (en) * 2017-06-14 2017-12-08 南京邮电大学 A kind of two indoles and three and the more arm configuration conjugated molecular materials of carbazyl and preparation method and application
CN107445968B (en) * 2017-06-14 2019-05-17 南京邮电大学 Two indoles of one kind and three and carbazyl multi-arm structure conjugated molecular material and the preparation method and application thereof
CN113861113A (en) * 2021-09-14 2021-12-31 中国科学院福建物质结构研究所 Preparation and application of fused ring pyridine compound and derivative thereof
CN118185506A (en) * 2024-05-20 2024-06-14 常州威斯敦粘合材料有限责任公司 Efficient UV-converted photovoltaic adhesive film and preparation method thereof

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