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A force- and light-responsive self-assembly based on dual fluorescent chromophores and its preparation method

A dual-response, self-assembly technology, applied in chemical instruments and methods, color-changing fluorescent materials, organic chemistry, etc., can solve problems such as difficult aggregates, lack of assembly driving force, and lack of attention, avoiding complex processes and achieving excellent crystallization. performance, easy to prepare effects

Active Publication Date: 2018-09-21
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the lack of assembly driving force, it is difficult for spiropyran molecules to self-assemble into aggregates with ordered and regular shapes.
Naphthalimides have excellent self-assembly properties due to the strong π-π interaction, but they have not received much attention in the field of mechanofluorochromic materials

Method used

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  • A force- and light-responsive self-assembly based on dual fluorescent chromophores and its preparation method
  • A force- and light-responsive self-assembly based on dual fluorescent chromophores and its preparation method
  • A force- and light-responsive self-assembly based on dual fluorescent chromophores and its preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035]

[0036] Spiropyran (SP-COOH) (300mg, 0.789mmol, structural formula as shown above) with a single carboxyl group and the condensing agent 2-(7-azobenzotriazole)-N,N,N' , N'-tetramethyluronium hexafluorophosphate (HATU) (600mg, 1.578mmol) was added to two reaction tubes, and then the basic reagent N,N-diisopropylethylamine (DIEA) (1.32mL, 8mmol ), then add 10mL of anhydrous N,N-dimethylformamide (DMF) until all the reactants are dissolved, stir evenly under nitrogen atmosphere and react at room temperature for 30min; then add naphthalimide (NI -NH 2 ) (227mg, 0.9mmol, the structural formula is as shown above), and the stirring reaction was continued at room temperature for 12h. After the reaction was complete, the excess solvent was removed by rotary evaporation, and the obtained solid crude product was dissolved with methanol (0.5-1 mL), and then precipitated with diethyl ether (30-50 mL). After centrifugation, the precipitate was collected, and the product was pur...

Embodiment 2

[0040] Take 10 mg (0.02 mmol) of P1 synthesized in Example 1 and dissolve it in 1 mL of dichloromethane, place it in a 10 mL vial, then add 1 mL of a mixed solvent of dichloromethane and n-hexane (v / v=1:1 ), and then add 6 mL of n-hexane. Single crystals can be grown after sealed storage for about 10 hours. The ORTEP diagram of the single crystal analysis and the fluorescence (under 365nm ultraviolet lamp irradiation) photos of the single crystal are as follows figure 2 shown.

Embodiment 3

[0042] Mechanofluorescent discoloration effect test: about 10mg (0.02mmol) of P1 synthesized in Example 1 was dissolved in 1.5mL of dichloromethane, added dropwise on the quartz plate, and the solvent was evaporated to dryness in a vacuum oven at 30 degrees Celsius. A mechanofluorescent color-changing film can be obtained, and the film initially has a fluorescent emission peak at 420nm. After erasing and writing with a mechanical force of 21Mpa, in addition to the fluorescence emission peak at 420nm, a new fluorescence emission peak appeared at 665nm. As the mechanical force increases to 32Mpa, the fluorescence emission peak intensity at 665nm also increases. After heat treatment, the new fluorescence emission peak at 665nm gradually weakens, and it can completely return to the original state after heating for 1 hour, and this process can be repeated many times. In order to represent this phenomenon more intuitively, we took pictures. We found that the initial P1 solid-state...

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Abstract

The invention relates to a power and light dual responses type self-assembly body based on dual flurophore and a preparing method thereof. By using spiropyrane and naphthalimides of the dual fluorophore, a molecular self-assembly body of which the morphology of molecular self-assembly can be adjusted and controlled is obtained through amidation. The molecular self-assembly body can be a power-induced fluorescent color material and has the advantages of being easy to erase, being able to return to an original state through a way of heating, and having good repeatability. Meanwhile, the self-assembly body has a light-induced fluorescent color performance, and the fluorescent maximum emission wavelength of the self-assembly body under the stimulation of mechanical force has a certain degree of red shift compared with light-induced fluorescent maximum emission wavelength, thus under the effect of the mechanical force, the assembly morphology of the self-assembly body can achieve the transformation from a fibrous shape to a globular shape. The self-assembly body is simple and convenient in preparing method, and can promote the applications of power-induced fluorescent color materials in practice.

Description

technical field [0001] The invention relates to the technical field of preparation of photoluminescence and photofluorescent color-changing materials and molecular self-assembly, in particular to a self-assembly with spiropyran and naphthalimide as fluorescent chromophores and a preparation method thereof. Background technique [0002] In recent years, stimuli-responsive materials have attracted attention because of their wide applications in biomedicine, chemical sensors, memory storage, and optoelectronic devices. Compared with other stimuli-responsive materials, mechanotropic and photofluorochromic materials have received special attention from researchers because force and light are readily available and easily adjustable stimuli-responsive sources. In addition, endowing synthetic materials with dual or multiple responsive properties at the same time has become a new research hotspot. Therefore, it is of great significance to effectively control the fluorescence properti...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D491/107C09K9/02
CPCC07D491/107C09K9/02C09K2211/1029C09K2211/1088
Inventor 尹梅贞莫申忠方兵
Owner BEIJING UNIV OF CHEM TECH
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