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Synthetic method of boroazaphenanthrene and derivatives thereof

A synthetic method and a phenanthrene technology, which is applied in the field of synthesis of borazaphenanthrene and its derivatives, can solve the problems that the potential application characteristics have not been widely developed.

Inactive Publication Date: 2019-01-18
TIANJIN UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The potential applications of boron-nitrogen-doped compounds in electronic devices have been widely studied, but their potential application characteristics in light-emitting materials have not been widely developed.

Method used

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  • Synthetic method of boroazaphenanthrene and derivatives thereof
  • Synthetic method of boroazaphenanthrene and derivatives thereof
  • Synthetic method of boroazaphenanthrene and derivatives thereof

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Experimental program
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preparation example Construction

[0033] A kind of overall synthetic method of borazine phenanthrene and its derivatives of the present invention comprises the following synthetic routes and steps:

[0034]

[0035] Some of the above-mentioned compounds are given examples, and the details are as follows:

Embodiment 1

[0036] Embodiment 1: the synthesis of 1,2-azaboraphenanthrene compound 1

[0037] 1) Synthesis of compound 4: Weigh 2-nitro-1-naphthol (1.0equiv, 27mmol, 5.07g) and add trifluoromethanesulfonic anhydride (1.25equiv, 34mmol, 9.5g) at 0°C, triethylamine (2.4equiv, 65mmol, 6.5g) was stirred at room temperature for 12h. After the reaction was complete, water and dichloromethane were added for extraction, the organic layers were combined, and dried over anhydrous magnesium sulfate, filtered, spin-dried, and quickly separated by column chromatography to obtain the target compound as a yellow solid (7.4 g, yield 85%);

[0038] 1 HNMR (400MHz, CDCl 3 ):δ8.26-8.30(m,1H,Ar),8.08(d,J=9.2Hz,1H,Ar),7.98-8.02(m,2H,Ar),7.78-7.83(m,2H,Ar) .

[0039] 2) Synthesis of Compound 5: Weigh 2-nitro-1-trifluoromethanesulfonic naphthalene (1.0equiv, 18.4mmol, 5.93g), tetrakistriphenylphosphine palladium (0.1equiv, 1.8mmol, 2.08g) , sodium carbonate (5.0equiv, 91.8mmol, 9.7g) was pumped for three t...

Embodiment 2

[0045] Embodiment 2: Synthesis of 1,2-azaboraphenanthrene derivatives

[0046] 5) Synthesis of Compound 12: Weigh 2-amino-1-vinylnaphthalene (1.0equiv, 5.0mmol, 850mg), add chlorobenzene in the glove box and stir to dissolve, then add triethylamine (1.5equiv, 7.5mmol, 1.05mL) and dichlorophenylborane (1.25equiv, 6.28mmol, 0.68mL) were placed at 130°C and heated to reflux for 12 hours. After the reaction was completed, water and dichloromethane were added for extraction. The organic layers were combined and dried over anhydrous magnesium sulfate. Filtration, spin-drying, and separation by column chromatography gave the white target compound (1.27 g, yield 99%).

[0047] 1 HNMR (400MHz, CDCl 3 ):δ9.10(d,J=12.0Hz,1H,Ar),8.58(d,J=8.8Hz,1H,Ar),8.41(br,1H,NH),7.98(dd,J 1 =8.0Hz,J 2 =2.0Hz, 2H, Ar), 7.89(t, J=6.8Hz, 2H, Ar), 7.64-7.67(m, 1H, Ar), 7.45-7.52(m, 6H, Ar).

[0048] 6) Synthesis of compound 13: Weigh 2-phenyl-1,2-azaborine (1.0equiv, 1.37mmol, 350mg), add dichlorometh...

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Abstract

The invention relates to a synthetic method of boroazaphenanthrene and derivatives thereof, tests the photoelectric physical property of the compounds and further researches potential application value of the organic material in the aspect of organic electrochemistry. The structural formula of the compound is described in the specification, wherein R1, R2, R3 and R4 are respectively independent substituted or non-substituted groups, including alkyl groups and aryl groups (benzene ring, thiophene ring, furan ring, pyrrole, pyridine, benzothiophene, benzofuran, benzopyrrole, benzoylpyridine, naphthalene ring, anthracene ring, phenalene, naphthacene, pyrene, chrysene, linear or angular pentacene, hexacene, indene and fluorene and the like), wherein R1 and R2 also can be single substituted halogen atom X: F, Cl, Br and I.

Description

technical field [0001] The present invention relates to a synthetic method of borazine phenanthrene and its derivatives. Using commercially available double-substituted naphthalene as raw material, boron nitrogen can be obtained through Suzuki coupling, metal reduction, and Lewis base-directed electrophilic borocyclization reaction. Heterophenanthrene compounds. The synthesis method has the characteristics of simple operation, mild reaction conditions, high yield, etc., and the compound can be applied to the field of organic photoelectric materials. Background technique [0002] Due to the unique space electronic structure of polycyclic aromatic hydrocarbons, it has many good application prospects in the field of optoelectronic materials such as organic field-effect transistors, organic light-emitting diodes, and organic photovoltaic cells. By introducing different heteroatoms such as B, N, P, O, S, Si, etc. into the full-carbon PAH skeleton, different optoelectronic proper...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02
CPCC07F5/02
Inventor 刘旭光张晨崔培培薛松
Owner TIANJIN UNIVERSITY OF TECHNOLOGY
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