A multi-stimulus-responsive organic small molecule light-emitting material and its preparation and application

A technology of luminescent materials and small molecules, applied in the fields of luminescent materials, organic chemistry, material excitation analysis, etc., can solve the problems of scarcity of stimuli-responsive luminescent materials, little correlation between stimulus-response luminescent compounds, and irregular design of luminescent compounds. , to achieve simple, feasible and effective design strategies, molecular weight determination, and good reproducibility

Active Publication Date: 2017-12-01
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, there are still very few reports on stimuli-responsive luminescent materials.
Generally speaking, there is basically little correlation between various reported stimulus-response luminescent compounds, and they are basically isolated events, and there is no rule that can be used for the design of this type of luminescent compounds.

Method used

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  • A multi-stimulus-responsive organic small molecule light-emitting material and its preparation and application
  • A multi-stimulus-responsive organic small molecule light-emitting material and its preparation and application
  • A multi-stimulus-responsive organic small molecule light-emitting material and its preparation and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] (1) Prepare synthetic raw material 4-bromobenzophenone;

[0036] (2) Preparation of multi-stimuli-responsive organic small molecule luminescent material P1, the specific synthesis route is shown in the following formula:

[0037]

[0038] The specific implementation steps are:

[0039] Under nitrogen protection, add 100ml of toluene, 1g of 4-bromobenzophenone (3.85mmol), 0.92g of phenothiazine (4.62mmol, 1.2equ) into the three-necked flask, and add 0.58g of tert-butyl alcohol under stirring Sodium, then add 38.5mg Pd(OAc) 2 (palladium acetate), tri-tert-butylphosphine, react overnight at 90°C. Cool down, extract the organic phase with dichloromethane, spin dry, and pass through the column. 1.17 g of a yellow solid product was obtained, with a yield of 80%. Molecular formula: C 25 h 17 NOS; M / Z=379.10 Theoretical: 379.10 (100.0%), 380.11 (27.0%), 381.10 (4.5%), 381.11 (2.7%), 382.10 (1.2%); Elemental analysis: C, 79.13; H, 4.52 ; N, 3.69; O, 4.22; S, 8.45.

Embodiment 2

[0041] (1) Prepare synthetic raw material 4-bromobenzophenone;

[0042] (2) Preparation of multi-stimuli-responsive organic small molecule luminescent material P2, the specific synthesis route is shown in the following formula:

[0043]

[0044] The specific implementation steps are:

[0045] Under nitrogen protection, add 100ml toluene, 1g 4-bromobenzophenone (3.85mmol), 1.5g intermediate 7 (N-p-phenylboronic acid phenothiazine) to the three-necked flask, and add 2M potassium carbonate under stirring Aqueous solution 25mL and 25mL ethanol, then add 200mg tetrakis (triphenylphosphine) palladium {Pd (PPh 3 ) 4}, react overnight at 90°C. After the reaction, the temperature was lowered, and the organic phase was extracted with dichloromethane, spin-dried, and passed through the column. 1.44 g of a yellow solid product was obtained, with a yield of 84%. Molecular formula: C 31 h 21 NOS; M / Z=379.10 Theoretical value: 517.08 (100.0%), 518.09 (33.5%), 519.09 (5.4%), 519.08 ...

Embodiment 3

[0051] (1) Preparation of intermediate 1, the specific synthetic route is shown in the following formula:

[0052]

[0053] The specific implementation steps are:

[0054] Under a nitrogen atmosphere, add 1.26g (8mmol) of 2-bromopyridine to a 100ml two-necked flask and dissolve it with 30ml THF; add 2.21g p-bromobenzaldehyde (12mmol, 1.5equ) to a 50ml eggplant-shaped flask and dissolve it with 20ml THF . The 2-bromopyridine tetrahydrofuran solution was cooled to -110°C with liquid nitrogen, argon was blown, and after 30 minutes of heat preservation, 3.2ml of 2.5M n-butyllithium (8mmol, 1equ) was slowly added dropwise. After dripping, react for one hour. After p-bromobenzaldehyde tetrahydrofuran was injected into the reaction system, the reaction was stirred at room temperature for three hours. After the reaction was completed, the tetrahydrofuran was evaporated to dryness, extracted three times with dichloromethane and water, and the yellow oil was obtained after the dic...

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Abstract

The invention belongs to the technical field of intelligent materials, and discloses a multi-stimulus-response organic small-molecular luminescent material, and preparation and application thereof. By utilizing the dual-fluorescence characteristics of phenothiazine derivatives, a series of luminescent materials are designed and synthesized; and external stimulus effects are utilized to regulate the reciprocal transformation of two conformations, thereby providing a simple feasible effective design strategy for the stimulus-response luminescent material. According to the preparation method, phenothiazine, which is used as a main reaction raw material, is subjected to a series of simple reactions to obtain various target products. The obtained product has the advantages of definite molecular weight, single structure, lower glass transition temperature and greatly higher stimulus-response sensitivity. The stimulus-response principle of the material is conversion between two different conformations instead of the influence of the intermolecular acting force and accumulation mode, so that the material has the multi-stimulus-response characteristic, and is applicable to sensors of force, temperature, pH and the like.

Description

technical field [0001] The invention belongs to the technical field of intelligent materials, and in particular relates to a multi-stimuli-response organic small molecule luminescent material and its preparation and application. Background technique [0002] "Smart material" is a new type of functional material that can sense external stimuli (such as external force, temperature, humidity, pH, electric field, magnetic field, etc.), can judge and process them appropriately, and can be executed by itself. Therefore, smart materials are also called stimulus-response materials. Smart materials are the fourth generation of materials following natural materials, synthetic polymer materials, and artificially designed materials. They are one of the important directions for the development of modern high-tech new materials. The boundaries between materials and structural materials are gradually disappearing, realizing functionalization of structures and diversification of functions....

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09K11/06G01N21/64C07D417/10C07D279/22
CPCC07D279/22C07D417/10C09K11/06C09K2211/1029C09K2211/1037C09K2211/1044C09K2211/1059G01N21/64
Inventor 苏仕健贺佐正彭俊彪曹镛
Owner SOUTH CHINA UNIV OF TECH
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