Preparation method and application of polynitro-substituted tetraphenyl ethylene compound

Abstract

The invention relates to a preparation method of a compound of formula (I). The method comprises the following steps: adding a tetraphenyl ethylene solution to a nitric acid and acetic acid mixed mixture for 5-15min to obtain an initial reaction mixture solution, and nitrating at 0-30DEG C, wherein a molar ratio of nitric acid to acetic acid in the mixture is 1:1.2-1:2; and in the initial reaction mixture solution, a molar ratio of tetraphenyl ethylene to nitric acid is 1:15-1:25, and the nitric acid content is 15-20wt%. The method has the advantages of simple synthesis route, cheap and easily available raw materials, high yield of the target product, and simple extraction and purification, is expected to realize large-scale commercialized production. The compound of the formula (I) and similar compounds of formula (II) have an inverse stimulation response fluorescence allochroism property, and can realize above two fluorescence colors. The invention also relates to a use of the compounds of the formula (I) and the formula (II) in inverse stimulation response fluorescence allochroism materials.

Description

technical field [0001] The invention belongs to the field of organic intelligent materials, and relates to the preparation and application of a polynitro-substituted tetraphenylethylene compound. The compound has the property of reversible stimulus-responsive fluorescent color change. Background technique [0002] Pressure-color fluorescent materials have been a hot topic of research by scientists in recent years. Pressure-color fluorescence means that under the action of shear force or pressure, the fluorescence emission wavelength or intensity of the compound changes significantly, and returns to the original state under the action of heat or solvent. The external force makes the compound change from one crystal structure to another crystal structure or amorphous structure, that is, the stacking mode changes, which also changes the fluorescent properties of the material. [0003] Sensors based on material pressure color fluorescence properties can be applied to the detect...

AI Technical Summary

Problems solved by technology

[0004] So far, the materials with fluorescent controllable discoloration based on molecular packing structure are very limited, and the synthesis of most of the target compounds has the following disadvantages: many steps, time-consuming, high raw material prices, cumbersome product purification, etc., large-scale production more difficult

In addition, there are disadvantages such as slow fluorescence transition speed, insufficient sensitivity to external force, and poor film-forming properties, which greatly limit the practical application of the material.

[0005] Some derivatives of tetraphenylethylene have good pressure-color fluorescence properties. Under the action of external force, like most other pressure-color fluorescent materials reported, they only show two kinds of fluorescent color changes, and the difference in fluorescence intensity is not large, which cannot satisfy The need for higher sensitivity

The fluorescence quenching effect of nitro group on most compounds is very obvious, so there is no report to introduce nitro group into fluorescent compounds to regulate their fluorescence properties

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