Boron nitrogen doped fused-ring aromatic hydrocarbon containing five-membered heterocyclic ring, synthesis method and application thereof

A technology for condensed aromatic hydrocarbons and five-membered heterocycles, which is applied in the field of boron-containing polycyclic aromatic heterocyclic organic compounds and their synthesis, and can solve problems such as changes in photophysical properties.

Active Publication Date: 2018-09-07
TIANJIN UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The introduction of the BN bond almost retains the spatial conformation of the all-carbon compound, but its photophysical properties change significantly (Bosdet, M.J.D.; Piers, W.E.Can.J.Chem.2009,87,8-29.)

Method used

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  • Boron nitrogen doped fused-ring aromatic hydrocarbon containing five-membered heterocyclic ring, synthesis method and application thereof
  • Boron nitrogen doped fused-ring aromatic hydrocarbon containing five-membered heterocyclic ring, synthesis method and application thereof
  • Boron nitrogen doped fused-ring aromatic hydrocarbon containing five-membered heterocyclic ring, synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0104]

[0105] The synthetic route of the BN phenanthrene compound of formula 15 pyrrole condensed

[0106] Synthesis of compound 4a: Weigh N-(2-nitrophenyl)pyrrole (1.9g, 9.90mmol, 1.00equiv) and dissolve it in 120ml of ethanol, place it at 0°C and stir for 30min, then weigh the base and slowly add it into the solution , the solution changed from light yellow to black, accompanied by gas generation. After the reaction was stable, it was stirred at room temperature overnight, then filtered, and the ethanol in the filtrate was spin-dried, and the spin-dried solid was washed with ethyl acetate and saturated salt It was extracted with water, dried over anhydrous magnesium sulfate, and subjected to column chromatography (PE:EA=10:1) to obtain a white solid 4a (1.2 g, 76%).

[0107] 1 H NMR (400MHz, CDCl 3 ):δ7.21–7.12(m,2H,Ar),6.84(t,J=2.4Hz,2H,Ar),6.76–6.83(m,2H,Ar),6.35(t,J=2.0Hz,2H ,Ar),3.71(br,2H,NH 2 ).

[0108] Synthesis of compound 5a: Weigh N-(2-aminophenyl)pyrrol...

Embodiment 2

[0111]

[0112] The synthetic route of the BN pyrene compound of formula sixteen pyrrole condensed

[0113] (1) Synthesis of compound 12a: Weigh N-(2,6-dinitrophenyl)pyrrole (1.4g, 5.8mmol, 1.0equiv) and dissolve it in 120ml of ethanol, place it at 0°C and stir for 30min, then weigh Alkali was slowly added into the solution, the solution changed from light yellow to black, accompanied by gas generation, after the reaction was stable, it was stirred overnight at room temperature, then filtered, the ethanol in the filtrate was spin-dried, and the spin-dried solid was washed with ethyl acetate The ester was extracted with saturated brine, dried over anhydrous magnesium sulfate, and subjected to column chromatography (PE:EA=4:1) to obtain white solid 12a (811.7 mg, 81%).

[0114] 1 H NMR (400MHz, CDCl 3 ): δ6.96(t, J=8.0Hz, 1H, Ar), 6.70(t, J=2.1Hz, 2H, Ar), 6.39(t, J=2.1Hz, 2H, Ar), 6.20(d, J = 8.0 Hz, 2H, Ar), 3.48 (br, 4H, NH).

[0115] (2) Synthesis of Compound 14a: Wei...

Embodiment 3

[0118]

[0119] The synthesis of the BN polycyclic aromatic hydrocarbon compound of formula 17 pyrrole condensing

[0120] (1) Synthesis of compound 17: Weigh compound 16 (44mg, 0.09mmol, 1.00equiv), sodium carbonate (48mg, 0.01mmol, 0.46equiv) and phenylboronic acid (28mg, 0.23mmol, 2.5equiv), weigh Pd (PPh 3 ) 4(10.5mg, 0.01mmol, 0.10equiv), add 1,4-dioxane and water (4:1), heat and stir for 12h, then extract with ethyl acetate and saturated brine, dry over anhydrous magnesium sulfate, filter , spin-dried, and column chromatography gave compound 17 (38mg, 87%).

[0121] (2) Synthesis of compound 18: Weigh compound 17 (37mg, 0.08mmol, 1.00equiv) and dissolve it with toluene (2ml), add triethylamine (33ul, 0.24mmol, 3.00equiv), boron tribromide (22ul, 0.24mmol, 3.0 equiv) heated and stirred (110° C.) for 24 h, then extracted with ethyl acetate and saturated brine, dried over anhydrous magnesium sulfate, filtered, spin-dried, and column chromatographed to obtain compound 1...

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Abstract

The invention relates to a boron nitrogen doped fused-ring aromatic hydrocarbon containing a five-membered heterocyclic ring, a synthesis method thereof and application thereof, the photoelectric physical properties of the boron nitrogen doped fused-ring aromatic hydrocarbon are tested, and the potential application value of the organic material in organic electrochemistry can be further studied.The improved synthesis method is used to make a reaction raw material low in price and easy to obtain, the reaction process avoids the use of toxic reagents, the synthesis method is simple and easy, and the compound is has a wide range of application in the fields of organic light emitting diodes, organic solar batteries, organic field effect transistors, organic lasers, organic sensors, molecularswitches, bio-imaging and toxin detection and the like.

Description

technical field [0001] The invention relates to boron-containing polycyclic aromatic heterocyclic organic compounds and their synthesis methods, as well as basic research on photoelectric physical properties. The synthesis methods involve electrophilic substitution, nucleophilic substitution, Suzuki coupling reactions, metallization reactions, and catalytic reactions. Physical property studies design absorption, emission and CV tests. Background technique [0002] In recent years, polycyclic aromatic hydrocarbons (PAHs) and their derivatives have received increasing attention in organic optoelectronic materials due to their modular synthesis and special optoelectronic physical properties (Wang, C.; Dong, H.; Hu , W.; Liu, Y.; Zhu, D.Chem.Rev.2012,112,2208-2267.), this type of compound is widely used and can be used in light-emitting materials, such as organic light-emitting diodes (OLED) (Sato, Y .; Ichinosawa, S.; Kanai, H. Operation Characteristics and Degradation of Orga...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06H01L51/00H01L51/54G01N21/64
CPCG01N21/6428C09K11/06C07F5/02C09K2211/1055G01N2021/6432H10K85/657Y02E10/549
Inventor 刘旭光李成龙
Owner TIANJIN UNIVERSITY OF TECHNOLOGY
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