Phthalimide organic light-emitting material with aggregation-induced emission and linear force stimulation-light-emitting color change response and application thereof

A phthalimide, aggregation-induced luminescence technology, applied in the direction of color-changing fluorescent materials, luminescent materials, organic chemistry, etc. Effects of non-radiative decay, high chemical and thermal stability

Active Publication Date: 2021-06-29
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the strong intermolecular interactions between traditional fluorescent molecules, fluorescence quenching is prone to o

Method used

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  • Phthalimide organic light-emitting material with aggregation-induced emission and linear force stimulation-light-emitting color change response and application thereof
  • Phthalimide organic light-emitting material with aggregation-induced emission and linear force stimulation-light-emitting color change response and application thereof
  • Phthalimide organic light-emitting material with aggregation-induced emission and linear force stimulation-light-emitting color change response and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0035] Example 1

[0036] The synthesis scheme of the adjacent phenylelimide organic luminescent material with aggregation induced luminescence and force stimulation - luminescent discoloration response is as follows:

[0037]

[0038] Compound 1 synthesis

[0039] In a 250 ml single-mouth bottle, nitrocyne (5.00 g, 20.08 mmol), carbazole (3.36 g, 20.08 mmol), copper iodide (764 mg, 4.02 mmol), sodium hydroxide (4.02 g, 100.40) Mmol), 1,10-o-affilitoline (724 mg, 4.02 mmol) and 60 mL toluene solution, magnetic stirring, nitrogen protection, heating and refluxed to 120 ° C, reaction 24h, TLC point plate tracking reaction degree. After the reaction is complete, the reaction is stopped, cooled to room temperature, poured into 250 ml of the separatory funnel, and extracted with dichloromethane (3 × 80 mL). Organic phase wash in distilled water, MGSO4 Dry, filtration, decreased volatile solvent, the residue is eluent with petroleum ether (PE) and dichloromethane (DCM) mixed solvent (...

Example Embodiment

[0054] Example 2

[0055] Compound 4 in Example 1 was in THF and H 2 O mixed solvent accompanying the photoluminescent spectrum of different water volume (0% -90%) (excitation wavelength 380 nm) figure 1 Indicated. As can be seen from Fig. 1, the compound 4 is weak in the THF solution, and the luminous intensity is significantly increased as the water content increases. Studies have shown that Compound 4 has excellent aggregation induced luminescence properties.

Example Embodiment

[0056] Example 3

[0057] The compound 5 in Example 1 was in THF and H 2 O mixed solvent accompanying the photoluminescence spectrum of different water volume fractions (0% -90%) (excitation wavelength 400 nm) figure 2 Indicated. As can be seen from Fig. 2, the compound 5 has bright light emitted in the THF solution. As the water content increases to 50%, the luminous intensity is gradually decreased; with further increase in water content, its luminous intensity is significantly enhanced. When the water content reached 90%, the luminous intensity is much higher than the luminous intensity in the pure THF solution. Studies have shown that compound 5 has excellent aggregation induced luminescence enhancement properties.

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Abstract

The invention belongs to the technical field of organic light-emitting materials, and particularly discloses a class of phthalimide organic light-emitting materials with aggregation-induced emission and linear force stimulation-light-emitting color change response, and application thereof. The light-emitting material comprises an asymmetric D-A-pi-D' or D-A-pi-A' structure, wherein a first electron donor (D) unit is phenothiazinyl or diarylamino, a first electron acceptor (A) unit is a rigid phthalimide group, the pi bridge is disubstituted phenyl, a second electron donor (D') unit is carbazolyl or substituted carbazolyl, and a second electron acceptor (A') unit is cyano. According to the invention, the organic light-emitting material has the linear force-induced color change characteristics of aggregation-induced emission and multi-stimulus response, and has wide application prospects in the fields of pressure sensors, optical data storage, memory chips, anti-counterfeiting marks and the like.

Description

technical field [0001] The invention belongs to the technical field of organic luminescent materials, and in particular relates to a phthalimide-based organic luminescent material with aggregation-induced luminescence and linear force stimulation-luminescence color change response and its application. Background technique [0002] Mechanoluminescent color-changing materials with multi-color switches are a new class of smart materials with mechano-stimuli-luminescence color-changing response function, which can exhibit obvious luminescence when stimulated by external forces (grinding, stretching or hydrostatic pressure). Color change has important potential application value in pressure sensors, information storage, memory chips, trademark anti-counterfeiting and many other fields, and has attracted the attention of many scientific researchers. Due to the strong intermolecular interactions between traditional fluorescent molecules, fluorescence quenching is prone to occur in ...

Claims

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Application Information

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IPC IPC(8): C07D209/48C07D209/86C07D417/04C07D417/14C09K9/02C09K11/06
CPCC07D209/86C07D417/14C07D209/48C07D417/04C09K11/06C09K9/02C09K2211/1029C09K2211/1037
Inventor 朱卫国杨慧芳吴秀刚朱梦冰谭华王亚飞刘煜张斌
Owner CHANGZHOU UNIV
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