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Pyrrole-ring-containing boron-oxygen-doped polycyclic aromatic hydrocarbon as well as synthesis method and application thereof

A technology of fused aromatic hydrocarbons and pyrrole rings, which is applied in the field of boron-containing polycyclic aromatic heterocyclic organic compounds and their synthesis, can solve the problems of lack of synthesis methods and instability, and achieve the effect of simple and easy synthesis methods

Pending Publication Date: 2022-04-05
TIANJIN UNIVERSITY OF TECHNOLOGY
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  • Abstract
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AI Technical Summary

Problems solved by technology

However, polycyclic aromatic hydrocarbons (oxaborines) containing BO bonds have not been well studied due to the lack of suitable synthetic methods and their instability (Misa Numano.; Naoto Nagami.; Soichiro Nakatsuka.; Takazumi Katayama.; Kiichi Nakajima. ; Sou Tatsumi.; Dr. Nobuhiro Yasuda.; Prof. Dr. Takuji Hatakeyama. Angew. Chem. Int. Ed. Engl. 2016, 22, 11574-11577.)

Method used

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  • Pyrrole-ring-containing boron-oxygen-doped polycyclic aromatic hydrocarbon as well as synthesis method and application thereof
  • Pyrrole-ring-containing boron-oxygen-doped polycyclic aromatic hydrocarbon as well as synthesis method and application thereof
  • Pyrrole-ring-containing boron-oxygen-doped polycyclic aromatic hydrocarbon as well as synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0081]

[0082] Formula 13 The synthetic route of the single BO-doped compound containing pyrrole ring

[0083] Synthesis of Compound 2: Weigh 2-methoxyaniline (218mg, 1.77mmol, 1.0equiv) and dissolve it in 5.00mL of glacial acetic acid, add 2,5-dimethoxytetrahydrofuran (0.23mL, 1.77mmol, 1.0equiv) . The reaction was stirred at 80°C for 4 hours. After cooling down to room temperature, it was extracted with dichloromethane and saturated aqueous sodium bicarbonate solution, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure, followed by column chromatography (eluent was petroleum ether:ethyl acetate=20:1) to obtain colorless liquid 2 (155mg, 51%).

[0084] 1 H NMR (400MHz, CDCl 3 ): δ7.27-7.35 (m, 2H, Ar), 7.00-7.08 (m, 4H, Ar), 6.35 (t, J=2.0 Hz, 2H, Ar), 3.86 (s, 3H, OCH 3 ).

[0085] Synthesis of compound 3b: under the protection of an inert gas atmosphere, weigh 1-(2-methoxyphenyl)-1H pyrrole (247mg, 1.43mmol, 1.00equ...

Embodiment 2

[0088]

[0089] The synthetic route of the double BO-doped compound of formula 14 containing pyrrole ring

[0090] Synthesis of Compound 5: Weigh 2,6-dimethoxyaniline (1.03g, 6.71mmol, 1.00equiv)) and dissolve it in glacial acetic acid (0.47mL), 1,2-dichloroethane (12.48mL) and water (7.52mL) in a mixed solvent, when the temperature was heated to 80°C, 2,5-dimethoxytetrahydrofuran (0.90mL, 7.05mmol, 1.05equiv) was added, and the reaction was stirred at 80°C for 11 hours, and then cooled to room temperature , extracted with dichloromethane and saturated brine, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure, followed by column chromatography (eluent: petroleum ether: ethyl acetate = 10:1) to obtain a white solid 5 ( 978 mg, 69%).

[0091] 1 H NMR (400MHz, CDCl3): δ7.28 (t, J=8.0Hz, 1H, Ar), 6.77 (t, J=2.0Hz, 2H, Ar), 6.67 (d, J=8.4Hz, 2H, Ar ), 6.33(t, J=2.0Hz, 2H, Ar), 3.78(s, 6H, OCH 3 ).

[0092] Synthesis of compoun...

Embodiment 3

[0095]

[0096] Formula 15 The synthetic route of the BN-BO doped compound containing pyrrole ring

[0097] Synthesis of compound 8: Weigh 2-methoxy 6-nitroaniline (522mg, 3.11mmol, 1.0equiv) and dissolve it in 20.00mL glacial acetic acid, add 2,5-dimethoxytetrahydrofuran (0.40mL, 3.11mmol , 1.0 equiv). The reaction was heated under reflux at 123°C for 2 hours, and after cooling down to room temperature, it was extracted with dichloromethane and saturated aqueous sodium bicarbonate, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure, followed by column chromatography (eluent (petroleum ether: ethyl acetate = 10:1) to obtain 8 (554 mg, 82%) as a yellow solid.

[0098] 1 H NMR (400MHz, CDCl 3 ): δ7.47 (dd, J 1 =8.4Hz,J 2 =8.4Hz, 1H, Ar), 7.40(dd, J 1 = 1.2Hz, J 2 =8.4Hz, 1H, Ar), 7.25(dd, J 1 = 1.2Hz,J 2 =8.4Hz, 1H, Ar), 6.73(t, J=2.4Hz, 2H, Ar), 6.36(t, J=2.0Hz, 2H, Ar), 3.87(s, 3H, OCH 3 ).

[0099] Synthesis of C...

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Abstract

The invention relates to pyrrole ring-containing boron-doped polycyclic aromatic hydrocarbon as well as a synthesis method and application thereof, and tests of photoelectric physical properties and CV are carried out on the pyrrole ring-containing boron-doped polycyclic aromatic hydrocarbon so as to further research the potential application value of the organic material in the aspect of organic electrochemistry. The structural formula of the compound is as follows: Ra and Rb are respectively and independently hydrogen, deuterium, alkyl, alkoxy, naphthenic base, ether, heterocyclic group, phenyl, aryloxy, halogen, cyano or a combination of the hydrogen, deuterium, alkyl, alkoxy, naphthenic base, ether, heterocyclic group, phenyl, aryloxy, halogen and cyano; rc may be hydrogen, deuterium, alkyl, alkoxy, cycloalkyl, ether, heterocyclic aryl, phenyl, aryloxy, or a combination thereof; ar is a benzene ring, a thiophene ring, a furan ring, a pyrrole ring, a pyridine ring, benzothiophene, benzofuran, benzopyrrole, benzopyridine, a naphthalene ring, an anthracene ring, phenalene, carbazolyl, pyrazinyl, triphenyl, tetraphenyl, pyrene, linear or angular pentacene, hexacene, indene and fluorene; m is an integer of 0-5; and n is an integer of 0-3.

Description

technical field [0001] The present 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 method involves Ullmann coupling reaction, Clauson-Kaas reaction, reduction reaction, nucleophilic substitution, etc., and research on photoelectric physical properties Involves UV, fluorescence and CV tests. Background technique [0002] In recent years, polycyclic aromatic hydrocarbons (PAHs) have attracted increasing attention in organic optoelectronic materials due to their unique electronic properties and modular synthesis of their derivatives (Wang, C.; Dong, H.; Hu, W.; Liu, Y.; Zhu, D. Chem. Rev. 2012, 112, 2208-2267.). In recent years, researchers have continued to innovate. On the basis of predecessors, they have developed from introducing a heteroatom into the conjugated PAH system to now doping two or more different heteroatoms into th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02
Inventor 刘旭光郭勇康
Owner TIANJIN UNIVERSITY OF TECHNOLOGY
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