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Binaphthol-based aggregation-induced light-emitting chiral fluorescent material

A technology for aggregation-induced luminescence and fluorescent materials, which is applied in the field of aggregation-induced luminescence chiral fluorescent materials to achieve good solubility effects

Inactive Publication Date: 2015-12-16
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Even so, from BINOL itself, it is still a great challenge to achieve AIE properties through simple molecular construction

Method used

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  • Binaphthol-based aggregation-induced light-emitting chiral fluorescent material
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  • Binaphthol-based aggregation-induced light-emitting chiral fluorescent material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] 1. Synthesis of BINOL-CHO

[0036]

[0037]Compound 1 (430 mg, 0.698 mmol) was dissolved in 6 mL THF under ice-water bath conditions, and then 3 mL concentrated hydrochloric acid was slowly added to the above solution. Then the mixture was allowed to warm to room temperature naturally and stirred for 3 hours. After the reaction was complete, the mixture was extracted with ethyl acetate (4×20 mL). The combined organic phases were washed successively with water, saturated sodium bicarbonate and saturated brine, and dried over anhydrous sodium sulfate. Subsequently, the solvent was evaporated under reduced pressure to obtain the product BINOL-CHO with a yield of 91%, and the structural characterization data were: 1 HNMR (400MHz, CDCl 3 , δ): 10.60 (s, 2H, CHO), 10.18 (s, 2H, OH), 8.34 (s, 2H, ArH), 8.00-7.98 (m, 2H, ArH), 7.44-7.38 (m, 4H, ArH), 7.22-7.20 (m, 2H, ArH); 13 CNMR (75MHz, CDCl 3 , δ): 196.92, 153.78, 138.65, 137.57, 130.83, 130.15, 127.78, 124.99, 124...

Embodiment 2

[0045] Synthesis of BINOM-CN

[0046]

[0047] Compound 1 (129 mg, 0.3 mol) was dissolved in 5 mL of ethanol, then malononitrile (40.6 mg, 0.615 mmol) and a drop of 1 mol / L NaOH aqueous solution were added, and stirred at room temperature for 2.5 hours. After the reaction was completed, the reactant was filtered under reduced pressure to obtain the target compound BINOM-CN with a yield of 46%, and the structural characterization data were: 1 HNMR (300MHz, CDCl 3 , δ): 8.94 (s, 2H, CH), 8.45 (s, 2H, ArH), 8.08 (d, J=8.0Hz, 2H, ArH), 7..60-7.55 (m, 2H, ArH), 7.50-7.45(m, 2H, ArH), 7.16(d, J=8.4Hz, 2H, ArH), 4.56(d, J=8.0Hz, 2H, CH 2 ), 4.50 (d, J=8.0Hz, 2H, CH 2 ), 3.09 (s, 6H, CH 3 ); 13 CNMR (75MHz, CDCl 3 , δ): 156.49, 152.26, 136.39, 131.78, 130.66, 130.30, 130.19, 127.14, 125.93, 125.61, 125.38, 113.85, 112.79, 100.68, 83.94, 57.50; ]+C 32 h 22 N 4 o 4 The theoretical value of Na is 549.1539, and the measured value is 549.1508.

Embodiment 3

[0049] Synthesis of BINOM-CN-Ph

[0050]

[0051] Compound 1 (108.5 mg, 0.25 mmol) was dissolved in 4 mL of ethanol, then phenylacetonitrile (58 μL, 0.5 mmol) and a drop of 1 mol / L NaOH aqueous solution were added, and stirred at room temperature for 2.5 hours. After the reaction was completed, the reactant was evaporated to remove the solvent under reduced pressure, and purified by column chromatography (petroleum ether / ethyl acetate=15:1) to obtain the target compound BINOM-CN-Ph, the yield was 53%, and the structural characterization data was : 1 HNMR (600MHz, CDCl 3 , δ): 8.86 (s, 2H, CH), 8.22 (s, 2H, ArH), 8.07 (d, J=6.0Hz, 2H, ArH), 7.79 (d, J=6.0Hz, 4H, ArH), 7.45-7.55(m, 6H, ArH), 7.35-7.43(m, 4H, ArH), 7.30(d, J=6.0Hz, 2H, ArH), 4.66(d, J=6.0Hz, 2H, CH 2 ), 4.62 (d, J=6.0Hz, 2H, CH 2 ), 2.80 (s, 6H, CH 3 ); 13 C-NMR (75MHz, CDCl 3 , δ): 152.22, 138.13, 134.82, 134.36, 130.64, 130.03, 129.55, 129.28, 128.35, 127.98, 126.16, 125.67, 117.99, 113.64, 100.15, 57...

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Abstract

The invention discloses a binaphthol-based aggregation-induced light-emitting chiral fluorescent material. The fluorescent material is prepared through simple condensation reaction carried out by taking chiral binaphthol with any structure as a framework and dicyanomethylidene as an electron acceptor. The fluorescent material disclosed by the invention has favorable solubility in a common organic solvent, is hardly dissolved into water, not only has aggregation-induced light-emitting property, but also shows an abnormal aggregation-induced CD signal quenching phenomenon so as to provide a new approach for constructing a binaphthol-based chiral sensor.

Description

technical field [0001] The invention belongs to the technical field of fluorescent materials, and in particular relates to a class of binaphthol-based aggregation-induced luminescent chiral fluorescent materials. Background technique [0002] Fluorescent materials have attracted great attention of scientists in recent years due to their great application value in optoelectronic devices, environmental sensors, biological sciences and other fields. Fluorescent materials have become indispensable tools in physics, chemistry, and biology. Although traditional fluorescent compounds show strong fluorescence in solution, most of them show a phenomenon of weakened or even quenched fluorescence in the aggregated state, which is the famous aggregation-induced fluorescence quenching effect (aggregation quenching emission, ACQ). Fluorescent materials are often used in an aggregated state or as a solid. For example: fluorescent dyes need to be in the water phase to enter cells, and hyd...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D213/30C07C255/37C07C253/30
Inventor 李楠赵娜冯红莲
Owner SHAANXI NORMAL UNIV
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