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Fluorescent materials with aggregation-induced emission effect and circular polarization and preparation method of fluorescent materials

A technology for aggregation-induced luminescence and fluorescent materials, which is applied to the preparation of the fluorescent materials and the field of circularly polarized fluorescent materials, can solve the problems of low repetition rate and many uncontrollable factors, and achieve high solid-state luminous efficiency and remarkable aggregation-induced luminescence characteristics. Effect

Inactive Publication Date: 2019-06-21
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In addition, there are many methods for self-assembly of chiral fluorescent materials by self-assembly methods, such as self-assembly by ultrasound, solvent volatilization, etc., but these methods have many uncontrollable factors and low repetition rate

Method used

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  • Fluorescent materials with aggregation-induced emission effect and circular polarization and preparation method of fluorescent materials
  • Fluorescent materials with aggregation-induced emission effect and circular polarization and preparation method of fluorescent materials
  • Fluorescent materials with aggregation-induced emission effect and circular polarization and preparation method of fluorescent materials

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] 1. Mix 342mg (1.0mmol) 2,2'-dihydroxy-[1,1'-binaphthyl]-3,3'-dimethylaldehyde, 150μL (1.25mmol) 1,6-dibromohexane, 1.38g (10mmol) potassium carbonate was added to 25mL N,N-dimethylformamide, stirred and reacted at 80°C for 12 hours, the reaction solution was extracted with ethyl acetate and saturated brine, the organic phases were combined, and dry column chromatography (with The volume ratio of petroleum ether to ethyl acetate is 20:1 as the eluent) to obtain the compound of formula I.

[0059]

[0060] 2. Dissolve 52 mg (0.123 mmol) of the compound of formula I in 3 mL of ethanol, add 20 mg (0.3 mmol) of malononitrile and 50 μL of 1 mol / L sodium hydroxide in ethanol, stir and react at room temperature for 3 hours, and concentrate under reduced pressure Ethanol was removed, and column chromatography (using a mixture of petroleum ether and ethyl acetate at a volume ratio of 20:1 as the eluent) yielded the target compound with a yield of 54%.

[0061]

[0062] The...

Embodiment 2

[0064] 1. Add 250mg (0.5mmol) compound of formula II and 414mg (6mmol) potassium carbonate to 25mL N,N-dimethylformamide, mix well, and then use a peristaltic pump to the resulting solution at a flow rate of 0.4mL / h Add 5 mL of N,N-dimethylformamide solution containing 825 μL (0.5 mmol) of 1,6-diiodohexane, stir and react at 80°C for 12 hours, extract the reaction solution with ethyl acetate and saturated brine, and combine The organic phase was subjected to dry column chromatography (using a mixture of petroleum ether and ethyl acetate at a volume ratio of 20:1 as the eluent) to obtain the compound of formula III.

[0065]

[0066] 2. 58 mg (0.1 mmol) of the compound of formula III, 57.6 mg (0.3 mmol) of 4-trifluoromethylbenzeneboronic acid shown in formula IV-1, 5 mg (0.02 mmol) of palladium acetate, 6 mg (0.02 mmol) of triphenyl Add phosphine and 83 mg (0.6 mmol) of potassium carbonate to a mixture of 2 mL of ethylene glycol dimethyl ether and deionized water at a volume...

Embodiment 3

[0072] In this example, the 4-trifluoromethylphenylboronic acid in Example 2 was replaced with an equimolar amount of phenylboronic acid, and the other steps were the same as in Example 2 to obtain a fluorescent material with the following structural formula, with a yield of 70%.

[0073]

[0074] The structural characterization data of the resulting product are: 1 H-NMR (600MHz, CDCl 3 )δ (ppm): 9.00 (s, 2H), 8.54 (s, 2H, Ar H), 8.22 (s, 2H, Ar H), 7.76 (d, 2H, J=8.9Hz, Ar H), 7.69 ( d, 4H, J=7.7Hz, Ar H), 7.50(t, 4H, J=7.6Hz, Ar H), 7.43-7.38(m, 4H, Ar H), 4.06-4.01(m, 2H, CH 2 ),3.74-3.69(m,2H,CH 2 ),1.77-1.74(m,2H,CH 2 ),1.52-1.47(m,2H,CH 2 ),1.39-1.34(m,2H,CH 2 ),1.11-1.08(m,2H,CH 2 ); 13 C-NMR (151MHz, CDCl 3 )δ(ppm):156.12,151.21,139.67,139.64,134.42,132.33,130.33,130.11,129.25,128.23,127.64,127.36,126.19,125.57,122.54,113.97,112.90,84.01,70.83,28.72,22.70;HRMS( ESI-TOF)m / z:[M+Na] + C 46 h 32 N 4 o 2 Na + Theoretical value 695.2417, measured value 695....

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Abstract

The invention discloses fluorescent materials with an aggregation-induced emission effect and circular polarization and a preparation method of the fluorescent materials. The general structural formula of the fluorescent materials is shown in the description, wherein R represents any one of H, phenyl, C1-C2 alkoxy substituted phenyl, C1-C3 alkyl substituted phenyl, trifluoromethyl substituted phenyl, thienyl, C1-C3 alkyl substituted thienyl and triphenylamine. After a ring-locking o-dinaphthol intermediate is synthesized from o-dinaphthol and 1,6-diiodohexane, a coupled product is synthesizedthrough a Suzuki coupling reaction, finally, an aldehyde group and malononitrile are subjected to a reaction, and the fluorescent materials are obtained. The fluorescent materials realize aggregation-induced emission characteristic and chirality in one molecular framework and can prevent quenching of circular dichroism spectrum, namely, the AACD effect, and by use of the two properties, microcrystals with different morphologies are obtained by self-assembly of the synthesized fluorescent materials, so that the compounds realize spectrum-adjustable circularly polarized light.

Description

technical field [0001] The invention belongs to the technical field of chiral fluorescent materials, and specifically relates to a kind of circularly polarized light fluorescent material with aggregation-induced luminescent properties, preventing circular dichroism quenching, and realizing adjustable spectrum, and a preparation method of the fluorescent material. Background technique [0002] The circular polarization chromatography (CPL) of chiral fluorescent materials has attracted more and more attention in recent years, because they can be used in optical display, encrypted transmission and storage of information, biological coding, optoelectronic devices, chiral optical materials, and even as a new material for asymmetric photochemical synthesis. catalyst. The preparation of materials with CPL properties should meet two conditions: the compound should have chirality and aggregation-inducing properties. At present, there are two most commonly used methods for preparing ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D321/00C07D409/14C09K11/06
Inventor 李楠赵娜张敏高旺旺
Owner SHAANXI NORMAL UNIV
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