Axial chirality-based binaphthol-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene complex and preparation method thereof

A technology of fluoroborate dipyrrole and binaphthol, which is applied in the field of organic functional luminescent materials, can solve problems such as complex synthesis steps, luminescence quenching, and high cost, and achieve the effects of low preparation cost, mild reaction conditions, and easy purification

Active Publication Date: 2020-01-10
NANJING FORESTRY UNIV
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Problems solved by technology

However, the following challenges still exist in the field of research on CPL-SOMs: 1) The luminescence asymmetry factor (g lum ) is relatively small, usually in the range of 10 -5 –10 -3 ; 2) There are few reports of CPL active compounds showing high quantum yields in solution and solid state at the same time, which is not o

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  • Axial chirality-based binaphthol-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene complex and preparation method thereof
  • Axial chirality-based binaphthol-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene complex and preparation method thereof
  • Axial chirality-based binaphthol-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene complex and preparation method thereof

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preparation example Construction

[0040] A kind of preparation method based on axial chiral binaphthol-fluoroboron dipyrrole complex of the present invention comprises the following steps:

[0041] (1) Add binaphthol (BINOL) to the first solvent, add sodium carbonate and methyl iodide to react, and obtain 2,2'-dimethoxy-1,1'-binaphthyl;

[0042] (2) Add the 2,2'-dimethoxy-1,1'-binaphthyl to the second solvent, and add n-butyllithium and N,N-dimethyl Base formamide, after warming up to room temperature, react to obtain 2,2'-dimethoxy-[1,1'-binaphthyl]-aldehyde;

[0043] (3) Add the 2,2'-dimethoxy-[1,1'-binaphthyl]-aldehyde to the third solvent, add 2,4-dimethylpyrrole, 2,3-dichloro -5,6-dicyano-1,4-benzoquinone stirring reaction;

[0044] (4) Add triethylamine and boron trifluoride ether solution to step (3), and continue to react for 5-10 hours to obtain the desired complex.

[0045] Described reaction process is:

[0046]

Embodiment 1

[0048] Add single-configuration BINOL (14.32g, 50mmol), anhydrous acetone and sodium carbonate (23.3g, 168.6mmol) into the reactor, add iodomethane (12.2mL, 196mmol) after stirring for 10 minutes, and continue stirring at 60°C 24 hours. After the reaction was completed, the solvent was removed, suction filtered, washed with water, and dried to obtain 14.9g of 2,2'-dimethoxy-1,1'-binaphthalene.

[0049]Anhydrous and oxygen-free operation, add 2,2'-dimethoxy-1,1'-binaphthalene (2.36g, 7.5mmol) and 120mL anhydrous THF into the reactor and stir to dissolve, slowly add n-butyl at -78°C Lithium (1.5M, 6 mL, 9 mmol) was stirred for 1 hour, DMF (1.2 mL, 15.5 mmol) was added at this temperature, and the reaction was continued at room temperature for 5 hours. After the reaction, the solvent was spin-dried, extracted with ethyl acetate / water, and separated on a silica gel column with petroleum ether and ethyl acetate at a volume ratio of 4:1 to obtain 2,2'-dimethoxy-[1 ,1'-binaphthyl]-...

Embodiment 2

[0055] Add single-configuration BINOL (14.32g, 50mmol), anhydrous acetone and sodium carbonate (23.3g, 168.6mmol) into the reactor, add iodomethane (12.2mL, 196mmol) after stirring for 10 minutes, and continue stirring at 50°C 30 hours. After the reaction was completed, the solvent was removed, suction filtered, washed with water, and dried to obtain 14.2 g of 2,2'-dimethoxy-1,1'-binaphthalene.

[0056] Anhydrous and oxygen-free operation, add 2,2'-dimethoxy-1,1'-binaphthalene (1.3g, 4.1mmol) and anhydrous THF 90mL into the reactor and stir to dissolve, slowly add n-butyl at 0°C Lithium (2.5M, 7.3mL, 18.3mmol) was stirred for 3 hours, DMF (2.6mL, 33.1mmol) was added at this temperature, and the reaction was continued at room temperature for 6 hours. After the reaction, the solvent was spin-dried, extracted with ethyl acetate / water, and separated on a silica gel column with petroleum ether and ethyl acetate at a volume ratio of 3:1 to obtain 2,2'-dimethoxy-[1 ,1'-binaphthyl]-...

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Abstract

The invention discloses an axial chirality-based binaphthol-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene complex and a preparation method thereof. The preparation method comprises the following steps: adding binaphthol into a first solvent, adding sodium carbonate and iodomethane, and performing a reaction so as to obtain 2,2'-dimethoxy-1,1'-binaphthalene; adding the 2,2'-dimethoxy-1,1'-binaphthalene into a second solvent, adding n-butyllithium and N,N-dimethyl formamide at -78 DEG C to 0 DEG C, increasing the temperature to room temperature, and performing a reaction so as to obtain 2,2'-dimethoxy-[1,1'-binaphthalene]-carboxaldehyde; adding the 2,2'-dimethoxy-[1,1'-binaphthalene]-carboxaldehyde into a third solvent, adding 2,4-dimethylpyrrole and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, and performing a stirring reaction; and adding triethylamine and a boron trifluoride diethyl etherate solution, and performing a reaction continuously for 5-10 hours, so as to obtain the desired complex. Through simple synthesis steps, the axial chirality-based binaphthol-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene complex is prepared, the preparation cost is low, the reaction condition is mild, purification is easy, and the synthesized compound has both an axial chirality structure of binaphthol and a fluorescence characteristic of a 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene complex.

Description

technical field [0001] The invention relates to an axial chiral binaphthol-fluoroboron dipyrrole complex and a preparation method thereof, belonging to the technical field of organic functional luminescent materials. Background technique [0002] Circularly polarized luminescence (CPL) has been favored by researchers due to its potential applications in 3D optical displays, organic light-emitting diodes (OLEDs), CPL lasers, and biological probes and imaging. So far, the compounds with CPL activity mainly focus on chiral metal complexes, organic helicene polymers and nanometer self-assembled materials. [0003] Recently, circularly polarized luminescent active small organic molecules (CPL-SOMs) have been generally accepted due to their advantages of facile synthesis, easy modification and tunable emission wavelength. However, the following challenges still exist in the field of research on CPL-SOMs: 1) The luminescence asymmetry factor (g lum ) is relatively small, usually ...

Claims

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Application Information

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IPC IPC(8): C07F5/02C09K11/06
CPCC07F5/022C09K11/06C09K2211/1055C09K2211/1011
Inventor 王小青姜志勇刘志鹏
Owner NANJING FORESTRY UNIV
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