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Axial chiral solid fluorescent material with helicene structure

A solid-state fluorescence and axial chiral technology, applied in the field of fluorescent materials, can solve the problems of low luminous efficiency of solid-state fluorescence and limit the practical application of chiral organic light-emitting materials, and achieve high absolute fluorescence quantum yield

Pending Publication Date: 2022-07-15
QINGDAO UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The disadvantage of low luminous efficiency of solid-state fluorescence largely limits the practical application of chiral organic light-emitting materials

Method used

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  • Axial chiral solid fluorescent material with helicene structure
  • Axial chiral solid fluorescent material with helicene structure
  • Axial chiral solid fluorescent material with helicene structure

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Example 1. Synthesis of Compounds (R)-BINOL[4]helicene-1 and (S)-BINOL[4]helicene-1

[0026] The reaction formula is as follows:

[0027]

[0028] 1) Add 3.2g (7.95mmol) (R)-2,2'-bis(methoxymethoxy)-[1,1'-binaphthyl]- to a 100ml round bottom flask under ice bath condition 3-aldehyde, 4.4 g (8.57 mmol) 4-bromobenzyltriphenylphosphine bromide, and 40 ml dry tetrahydrofuran. After the reactants were completely dissolved, 5.9 g (61.4 mmol) of sodium tert-butoxide was added to the reaction solution in batches, and the reaction was carried out under ice bath conditions for 4 h. Water was added to quench the reaction, dichloromethane was added to the reaction solution, the organic phase obtained by separation was dried with anhydrous sodium sulfate, filtered, and the solvent was removed by rotary evaporation, and 4.1 g of (R,E)-3-( 4-Bromostyryl)-2,2'-bis(methoxymethoxy)-1,1'-binaphthyl, 95% yield.

[0029] 2) Under nitrogen protection, add 0.2g (0.36mmol) (R,E)-3-(4-bro...

Embodiment 2

[0034] Example 2. Synthesis of Compounds (R)-BINOL[4]helicene-2 ​​and (S)-BINOL[4]helicene-2

[0035] The reaction formula is as follows:

[0036]

[0037] Under nitrogen protection, add 300mg (0.60mmol) (R)-2-bromo-7-methoxy-8-(2-(methoxy)naphthalen-1-yl)benzo[c] to a 100ml three-necked flask phenanthrene, 24 mg (0.11 mmol) palladium acetate and 82.5 mg (0.27 mmol) tri-o-methylphenylphosphine, then 25 ml dry DMF and 20 ml triethylamine were added. The solution was heated to 45° C. for 0.5 h, and 93 mg (0.72 mmol) of 4-vinyl benzonitrile was added. Then the solution was warmed to 115°C and reacted for 5h. DMF and triethylamine were removed by rotary evaporation, and dichloromethane was added to the solution. The organic phase was washed with water, spin-dried, and separated by column chromatography to obtain 0.19 g of (R, E)-4-(2-(7-methoxy-8-(2-methoxynaphthalen-1-yl)benzo[c] ]phenanthren-2-yl)vinyl)benzonitrile (R)-BINOL[4]helicene-2 ​​in 64% yield. 1 HNMR (500MHz, C...

Embodiment 3

[0040] Example 3. Synthesis of Compounds (R)-BINOL[4]helicene-3 and (S)-BINOL[4]helicene-3

[0041] The reaction formula is as follows:

[0042]

[0043] Under nitrogen protection, add 300mg (0.60mmol) (R)-2-bromo-7-methoxy-8-(2-(methoxy)naphthalen-1-yl)benzo[c] to a 100ml three-necked flask phenanthrene, 24 mg (0.11 mmol) palladium acetate and 82.5 mg (0.27 mmol) tri-o-methylphenylphosphine, then 25 ml dry DMF and 20 ml triethylamine were added. The solution was heated to 45° C. for 0.5 h, and 97 mg (0.72 mmol) of 4-methoxystyrene was added. Then the solution was warmed to 115°C and reacted for 5h. DMF and triethylamine were removed by rotary evaporation, and dichloromethane was added to the solution. The organic phase was washed with water, spin-dried, and separated by column chromatography to obtain 0.20 g of (R, E)-7-methoxy-8-(2-methoxynaphthalen-1-yl)-2-(4-methoxybenzene) Vinyl)benzo[c]phenanthrene(R)-BINOL[4]helicene-3, 62% yield. 1 HNMR (500MHz, CDCl 3 )δ9.17(...

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Abstract

The invention discloses an axially chiral solid fluorescent material with a helicene structure, and belongs to the technical field of fluorescent materials. The axially chiral solid-state fluorescent compound provided by the invention has the characteristics of an axially chiral structure and a helicene structure. The solid-state fluorescent compound can emit bright blue fluorescence in an organic solvent and in a solid state, and has relatively high fluorescence quantum yield. The enantiomer of the fluorescent compound has obvious circular dichroism, and can show a circularly polarized luminescence property after being excited. The axial chiral fluorescent material disclosed by the invention has excellent solid-state fluorescence luminous efficiency and chiral optical performance, and has potential application value in the photoelectric field.

Description

【Technical field】 [0001] The invention belongs to the technical field of fluorescent materials, in particular to an axial chiral solid fluorescent material with a helicene structure. 【Background technique】 [0002] Chiral fluorescent functional materials have broad application prospects in optical detectors, biological probes, three-dimensional optical displays, optical storage devices, and optoelectronic devices (Acta Chim. Sinica, 2017, 75, 1150-1163). Chiral organic light-emitting materials are an important class of chiral fluorescent functional materials, which have the characteristics of easy derivatization of molecular structure, high molecular luminescence efficiency, and various molecular species. At present, researchers have developed a variety of chiral organic light-emitting materials, which can be divided into central chirality (Org. Lett., 2016, 18, 2719-2721), face chirality (J.Am. Chem.Soc., 2014, 136, 3350-3353), axial chirality (J.Am.Chem.Soc., 2020, 142, 1...

Claims

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Application Information

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IPC IPC(8): C07C41/48C07C43/30C07C41/28C07C43/225C07C41/30C07C43/215C07C253/30C07C255/54C07D213/30C09K11/06
CPCC07C41/48C07C43/30C07C41/28C07C43/225C07C41/30C07C43/215C07C253/30C07C255/54C07D213/30C09K11/06C09K2211/1007C09K2211/1011C09K2211/1029
Inventor 陈绍晋胡志强刘春芳原春鸣贾柯刘晶王鲲鹏
Owner QINGDAO UNIV OF SCI & TECH
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