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 occur in the solid state, which greatly limits the development and application of mechanoluminescent color-changing materials.

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

Embodiment 1

[0036] The synthesis scheme of phthalimide-based organic light-emitting materials with aggregation-induced luminescence and force-stimulation-luminescence color-changing response is as follows:

[0037]

[0038] Synthesis of compound 1

[0039] In a 250mL single-necked bottle, add p-nitroiodobenzene (5.00g, 20.08mmol), carbazole (3.36 g, 20.08mmol), cuprous iodide (764mg, 4.02mmol), sodium hydroxide (4.02g, 100.40 mmol), 1,10-phenanthroline (724mg, 4.02mmol) and 60mL toluene solution, magnetically stirred, nitrogen protection, heated to reflux to 120°C, reacted for 24h, followed the degree of reaction by TLC spot plate. After the reaction was complete, the reaction was stopped, cooled to room temperature, poured into a 250 mL separatory funnel, and extracted with dichloromethane (3×80 mL). The organic phase was washed with distilled water, MgSO4 Dry, filter, and distill under reduced pressure to remove volatile solvents, and the residue is separated by column chromatograph...

Embodiment 2

[0055] Compound 4 in Example 1 was in THF and H 2 The photoluminescence spectrum (excitation wavelength is 380nm) under the condition of different water volume fractions (0%-90%) in O mixed solvent is as follows figure 1 shown. It can be seen from Figure 1 that compound 4 emits weakly in THF solution, and its luminescence intensity increases significantly with the increase of water content. Studies have shown that compound 4 has excellent aggregation-induced luminescent properties.

Embodiment 3

[0057] Compound 5 in Example 1 was in THF and H 2 The photoluminescence spectrum (excitation wavelength is 400nm) under the condition of different water volume fractions (0%-90%) in O mixed solvent is as follows figure 2 shown. It can be seen from Figure 2 that compound 5 has bright luminescence in THF solution, and the luminescence intensity gradually decreases as the water content increases to 50%, and its luminescence intensity increases significantly as the water content further increases. When the water content reaches 90%, the luminescence intensity is much higher than that in pure THF solution. Studies have shown that compound 5 has excellent aggregation-induced luminescence enhancement performance.

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PUM

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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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