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Aggregation-induced luminescent aniline derivative luminescent compound and preparation method thereof

An aggregation-induced luminescence, aniline derivative technology, applied in the preparation of organic compounds, the preparation of aminohydroxy compounds, chemical instruments and methods, etc., can solve the problems of health effects, time-consuming and labor-intensive, etc. Easy to obtain, linear detection effect

Active Publication Date: 2021-07-16
BEIHANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

N-hexane is a low-toxicity solvent, which is widely used in daily life production, but the residual poison benzene is often contained in the manufacturing process of n-hexane, which has a great impact on people's health
At present, the detection of benzene in n-hexane mainly uses highly complex analytical methods, such as gas chromatography and headspace gas chromatography, which are time-consuming and labor-intensive

Method used

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  • Aggregation-induced luminescent aniline derivative luminescent compound and preparation method thereof
  • Aggregation-induced luminescent aniline derivative luminescent compound and preparation method thereof
  • Aggregation-induced luminescent aniline derivative luminescent compound and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0044] Preparation of Aniline Derivatives Luminescent Compounds with AIE Properties

[0045] In this example, aniline derivative-based luminescent compounds containing different side groups were synthesized by a simple and effective method with a yield of 55-75%, and their chemical structures were fully characterized by H NMR and mass spectrometry.

[0046] The detailed synthesis method is as follows:

[0047] The first step: diphenylamine (diphenylamine: 0.642g, 3.8mmol; 4-bromo-diphenylamine: 0.939g, 3.8mmol; 4-hydroxyl-diphenylamine: 0.703g, 3.8mmol; 4-diphenylamine: 0.703g, 3.8mmol; Methoxy-diphenylamine: 0.757g, 3.8mmol and 4-nitro-diphenylamine: 0.813g, 3.8mmol), diphenylacetaldehyde (0.745g, 3.8mmol), Molecular sieves (1.011g), toluene (8ml) and tetrahydrofuran (2ml) were vigorously mixed and stirred for 20 minutes, and (±)-camphor-10-sulfonic acid (catalyst amount) was added; then the temperature was raised to 110°C, carry out stoxenamine reaction, keep 110°C and ...

Embodiment 2

[0051] Study on Photophysical Properties of Aniline Derivatives Luminescent Compounds Containing Different Side Groups

[0052] Such as figure 2 As indicated, the UV spectra of aniline derivatives modified with different side groups were tested. It is calculated that the aniline derivatives with different side groups have strong light absorption ability. Compounds B1-A1, Br-B1-A1, HO-B1-A1, MeO-B1-A1 and NO 2 -B1-A1 molar extinction coefficients are 20550, 23626, 27154, 24173 and 17900cm respectively -1 .mol -1 .L.

[0053] Further, the fluorescence emission behavior of aniline derivatives containing different side groups in pure THF solvent and THF / water mixed solvent was investigated. The fluorescence intensity of compounds B1-A1 and Br-B1-A1 did not change significantly with the increase of water volume fraction in THF / water mixed solvent; while compounds HO-B1-A1, MeO-B1-A1 and NO 2 -B1-A1 As the volume fraction of water in the THF / water mixed solvent increases, t...

Embodiment 3

[0055] Force-responsive Luminescence Study of Compound MeO-B1-A1

[0056] Take the compound MeO-B1-A1 obtained in Example 1, that is, 0.4 g of yellow-green crystals, and dry it in a vacuum oven at 40° C. for 2 hours. After drying is complete, the yellow-green crystals are placed in a mortar and divided into two equal parts.

[0057] Grind the right half well with a pestle and wait for comparison. Such as Figure 4 As shown, under the sunlight, the shape of the ground MeO-B1-A1 changed from yellow crystal to light yellow powder; under the irradiation of 365nm ultraviolet light, the color of the emitted light changed from cyan to cyan.

[0058] Studies have shown that the compound MeO-B1-A1 will have a significant change in luminescent color under the action of external force grinding, which can be used in force-responsive smart materials, preferably in force-stimuli-responsive materials for external force sensors, anti-counterfeiting labels, and information storage.

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Abstract

The invention discloses an aggregation-induced luminescent aniline derivative luminescent compound, a preparation method and an application thereof. The luminescent compound of aniline derivatives includes chemical formula I, and the corresponding luminescent compounds of aniline derivatives are B1‑A1, Br‑B1‑A1, HO‑B1‑A1, MeO‑B1‑A1 and NO 2 ‑B1‑A1. Among them, B1‑A1 and Br‑B1‑A1 do not exhibit obvious AIE characteristics, while HO‑B1‑A1, MeO‑B1‑A1 and NO 2 ‑B1‑A1 all show obvious AIE characteristics; MeO‑B1‑A1 will have obvious changes in luminescent color under the action of external force grinding, which can be used for force-responsive smart materials; NO 2 ‑B1‑A1 showed a high sensitivity response to solvent polarity changes, enabling fast, efficient and linear detection of toxic substances (trace amounts of benzene) in food-grade n-hexane.

Description

technical field [0001] The invention belongs to the technical field of luminescent materials, and in particular relates to an aniline derivative luminescent compound with aggregation-induced emission (aggregation-induced emission, AIE) characteristics, a preparation method and application thereof. Background technique [0002] The commonly referred to AIE phenomenon refers to the phenomenon that the luminescent material hardly emits light in a dilute solution, but emits strongly in an aggregated state. Compounds with AIE properties have fundamentally overcome the problem of aggregation caused quenching (ACQ), and have received extensive attention. However, traditional AIE molecules are mainly based on hydrocarbon chain backbones, such as triphenylethylene, tetraphenylethylene, and tetraphenyl-1,4-butadiene, while heteroatom backbone AIE molecules are rarely involved. [0003] In fact, heteroatom-containing π-conjugated organic molecules generally have good electrochemical, ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C209/60C07C211/48C07C211/52C07C213/08C07C215/76C07C217/84C09K11/06C09K9/02G01N21/64
CPCC07C211/48C07C211/52C07C215/76C07C217/84C09K9/02C09K11/06C09K2211/1007C09K2211/1014G01N21/6428G01N21/643
Inventor 杨继萍陆浩刘蓓蓓王萌黄明明
Owner BEIHANG UNIV
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