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A piezochromic fluorescent molecule and its preparation method and application

A fluorescent molecule, piezochromic technology, applied in the direction of color-changing fluorescent materials, chemical instruments and methods, imino compound preparation, etc. Effect

Active Publication Date: 2019-08-16
NANJING TECH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, few luminescent materials with piezochromic properties have been reported so far.

Method used

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  • A piezochromic fluorescent molecule and its preparation method and application
  • A piezochromic fluorescent molecule and its preparation method and application
  • A piezochromic fluorescent molecule and its preparation method and application

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preparation example Construction

[0049] The present invention provides a method for preparing piezochromic fluorescent molecules described in the above technical solution, comprising the following steps:

[0050] (1) Mix 1,1,3,3-tetramethoxypropane, arylamine and an organic solvent to obtain a mixed solution; the arylamine is aniline or p-bromoaniline;

[0051] (2) Cool down the mixed solution obtained in the step (1) to -5-5°C, add acid solution dropwise, carry out hydrolysis and nucleophilic addition reaction, and obtain piezochromic fluorescent molecules.

[0052] The invention mixes 1,1,3,3-tetramethoxypropane, arylamine and organic solvent to obtain a mixed solution. In the present invention, the arylamine is aniline or p-bromoaniline. In the present invention, when the arylamine is aniline and p-bromoaniline, the obtained products correspond to compounds in which R in formula I is R1 and R3, respectively. In the present invention, there is no special limitation on the ratio of the 1,1,3,3-tetramethoxypr...

Embodiment 1

[0067] The synthesis of N-((1E)-3-(phenylimino) prop-1-en-1-yl) aniline hydrochloride (N1), the reaction equation is as follows:

[0068]

[0069] Add 3.284g (0.02mol, 1eq.) of 1,1,3,3-tetramethoxypropane, 3.720g (0.04mol, 2eq.) of aniline and 50ml of absolute ethanol into a 100mL two-necked flask, stir to dissolve completely Cool the solution to 0°C, slowly add 4ml of concentrated hydrochloric acid dropwise within 15 minutes with a constant pressure dropping funnel, continue to stir at room temperature for 1-2 hours after the dropwise addition, a yellow solid precipitates, filter with suction, wash the filter cake with water and ethanol respectively After 3 times of vacuum drying, an orange-yellow product was obtained with a yield of 55%.

[0070] Test results: 1H NMRδ12.70(s, 2H), 8.925(d, J=6.0Hz, 2H), 7.43-7.50(m, 8H), 7.25(t, J=4.0Hz, 2H), 6.51(t, J=12Hz,1H),

[0071] Elemental Analysis: Grouped C 15 h 15 ClN 2 .

[0072] Theoretical calculations: C, 69.63; H, 5....

Embodiment 2

[0087] The synthesis of 4-bromo-N-((1E)-3-((4-bromophenyl)imino)prop-1-en-1-yl)aniline hydrochloride (N3) is as follows:

[0088]

[0089] The process is the same as in Example 1, except that the reactant aniline is replaced by p-bromoaniline, and the yellow product is obtained by vacuum drying with a yield of 83%.

[0090] Test results: 1H NMRδ12.74(s, 2H), 8.815(d, J=6.0Hz, 2H), 7.70(d, J=4.0Hz, 4H), 7.37(d, J=4.0Hz, 4H), 6.51 (t, J = 12Hz, 1H).

[0091] Elemental analysis: Molecular formula C 15 h 13 Br 2 ClN 2 .

[0092] Calculated theoretically: C, 43.25; H, 3.15; N, 6.73.

[0093] Actual measured values: C, 43.29; H, 3.13; N, 6.70.

[0094] High resolution mass spectrometry: Calculated value of ion peaks [M-Cl - ]: 380.9440.

[0095] Measured value: 380.9436.

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Abstract

The invention provides a piezochromic fluorescent molecule and a preparation method and application thereof. The piezochromic fluorescent molecule has an aggregation-induced emission property; besides, a compound is transformed into an amorphous state from an original crystalline state under the action of pressure, the accumulation mode in a solid state is changed, and thus the change of emissionspectra is caused; the compound is transformed into the crystalline state from the amorphous state after fumigation, and thus a piezallochromy property is achieved. Experimental results show that thepiezochromic fluorescent molecule has good solubility in dimethyl sulfoxide but is almost insoluble in dichloromethane, can form nano-aggregate, and has the aggregation-induced emission property. In addition, the solid emission color ranges from yellow-green light to orange-yellow light; the solid emission color change can be obviously observed under a 365 nm ultraviolet lamp after the action of pressure, and meanwhile the original emission color can be restored under the fumigation of methanol steam.

Description

technical field [0001] The invention relates to the technical field of photoelectric functional materials, in particular to a piezochromic fluorescent molecule and its preparation method and application. Background technique [0002] In recent years, due to their wide application value in OLED optoelectronic devices, biosensors, information security and other fields, fluorescent molecules have attracted the attention of many scientific researchers. However, traditional fluorescent compounds exhibit high luminescence efficiency in solution, and the fluorescence intensity is weakened or even quenched in the aggregated state, which is the common aggregation-induced quenching effect (ACQ). Given that fluorescent materials are often used in the form of aggregates or solid films, the ACQ phenomenon severely limits the application prospects of fluorescent materials in specific situations. [0003] In 2001, Academician Tang Benzhong's research group reported a class of molecules wi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09K9/02C07C251/30C07C249/02H04L9/08
CPCC07C249/02C07C251/30C09K9/02C09K2211/1007H04L9/0861
Inventor 刘睿胡锦阳朱红军汪佳宋广亮朱森强黎杨陆佳鹏
Owner NANJING TECH UNIV