Fluorescent material with properties of aggregation-induced emission and piezochromism

A technology of aggregation-induced luminescence and fluorescent materials, applied in the field of fluorescent materials with aggregation-induced luminescence properties and piezochromic properties

Inactive Publication Date: 2016-12-07
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are not many luminescent materials with piezochromic properties reported so far, so there is still an urgent need to design and synthesize new aggregation-induced luminescent materials with piezochromic properties.

Method used

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  • Fluorescent material with properties of aggregation-induced emission and piezochromism
  • Fluorescent material with properties of aggregation-induced emission and piezochromism
  • Fluorescent material with properties of aggregation-induced emission and piezochromism

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Synthesis of 1,4-diphenyl-2,2'-(1,4-phenylenebis(methylene))malononitrile with the following structural formula

[0043]

[0044] 1. Mix 0.0584g (0.2mmol) 2,5-dibromobenzene-1,4-dicarbaldehyde, 0.27mL DMF, 0.13mL 2mol / LNa 2 CO 3Aqueous solution, 0.0609g (0.5mmol) phenylboronic acid was added in 5mL round-bottomed flask, after stirring for 10 minutes, 0.0424g (0.01mmol) palladium acetate was added to the reaction solution, after the reaction was completed, extracted with ethyl acetate (3× 5mL), combined the organic phase, the organic phase was dried over anhydrous sodium sulfate, filtered, spin-dried, and the volume ratio of petroleum ether and ethyl acetate was 20:1 mixed liquid column chromatography to obtain 1,1':4', 1"-terphenyl-2',5'-dicarbaldehyde.

[0045] 2. Add 0.0400g (1.05mmol) 1,1':4',1"-terphenyl-2',5'-dicarbaldehyde to a 25mL round bottom flask, add absolute ethanol to dissolve it, and then add 0.1419 g (2.15mmol) malononitrile and 0.05mL 1mol / L NaOH ...

Embodiment 2

[0047] Synthesis of 1,4-bis(3-furyl)-2,2'-(1,4-phenylenebis(methylene))malononitrile with the following structural formula

[0048]

[0049] The phenylboronic acid in Example 1 was replaced with 3-furanboronic acid of the same amount, and the other steps were the same as in Example 1 to obtain 1,4-bis(3-furyl)-2,2'-(1,4 -Phenylene bis(methylene)) malononitrile, its productive rate is 63%, and the structural characterization data is: 1 H-NMR (300MHz, CDCl 3 )δ (ppm): 8.24 (s, 1H), 8.05 (s, 1H), 7.64 (t, 1H, J = 1.6Hz), 7.55 (s, 1H), 6.62-6.61 (q, 1H); 13 C-NMR (101MHz, CDCl 3 )δ (ppm): 157.36, 145.09, 142.34, 134.28, 132.85, 130.21, 122.40, 112.82, 111.99, 111.35, 87.65. HRMS (ESI-TOF) m / z: [M+Na] + Theoretical value C 22 h 10 N 4 o 2 Na, 385.0701, found 385.0703.

Embodiment 3

[0051] Synthesis of 1,4-bis(4-methoxyphenyl)-2,2'-(1,4-phenylenebis(methylene))malononitrile with the following structural formula

[0052]

[0053] The phenylboronic acid in Example 1 is replaced with 4-methoxyphenylboronic acid of the same amount of substance, and other steps are the same as in Example 1 to obtain 1,4-bis(4-methoxyphenyl)-2,2 '-(1,4-phenylene bis(methylene)) malononitrile, the yield is 69%, and the structural characterization data are: 1 H-NMR (400MHz, CDCl 3 )δ (ppm): 8.22 (s, 1H), 7.84 (s, 1H), 7.27 (d, 2H, J = 8.5Hz, Ar H), 7.07 (d, 2H, J = 8.5Hz, Ar H), 3.91(s,3H,CH 3 ); 13 C-NMR (101MHz, CDCl 3 )δ (ppm): 160.97, 158.77, 142.91, 132.79, 131.50, 130.76, 128.94, 115.03, 113.09, 112.29, 86.53, 55.69. HRMS (ESI-TOF) m / z: [M+Na] + Theoretical value C 28 h 18 N 4 o 2 Na, 465.1327, found 465.1330.

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PUM

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Abstract

The invention discloses a fluorescent material with properties of aggregation-induced emission and piezochromism. A structural formula of the fluorescent material is as shown in the specification. The fluorescent material is prepared through a simple condensation reaction by taking dicyanomethylene as an electron acceptor. The fluorescent material is high in solubility in common organic solvents but hardly dissolved in water and forms nano aggregates, so that the characteristic of aggregation-induced emission is achieved. By grinding, fluorescence emission wavelength of the fluorescent material moves towards a long wave direction and recovers after fumigation with dichloromethane, so that the property of piezochromism is achieved.

Description

technical field [0001] The invention belongs to the technical field of fluorescent materials, in particular to a class of fluorescent materials with aggregation-induced luminescent properties and piezochromic properties. 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. Traditional fluorescent compounds show strong fluorescence in solution, but most of them exhibit fluorescence weakening or even quenching in the aggregated state, which is called aggregation-caused quenching (ACQ). Since fluorescent materials are often used as aggregates or solid films, the ACQ phenomenon limits the application prospects of fluorescent materials in specific situations. In 2001, the research group of Academician Tang Benzhong of the Hong Kong University of Science and Technology discovered that a class of mo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C255/34C07D407/10C07C255/37C07C255/36C07D409/10C07D403/10C07F7/18C09K11/06
CPCC07C255/34C07C255/36C07C255/37C07D403/10C07D407/10C07D409/10C07F7/1804C09K11/06
Inventor 李楠赵娜张静楠康辉
Owner SHAANXI NORMAL UNIV
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