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Fluorescent naphthalene calix[3]arene non-porous self-adaptive crystal, and preparation method and application thereof

A self-adaptive, naphthalene ring technology, applied in ether preparation, organic chemistry methods, chemical instruments and methods, etc., to achieve the effect of avoiding the aggregation-induced fluorescence quenching phenomenon of macrocyclic molecules, simple operation and high yield

Pending Publication Date: 2022-01-04
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] To overcome the deficiencies of existing technologies in artificial light trapping, fabricate non-porous adaptive crystal materials with larger cavities

Method used

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  • Fluorescent naphthalene calix[3]arene non-porous self-adaptive crystal, and preparation method and application thereof
  • Fluorescent naphthalene calix[3]arene non-porous self-adaptive crystal, and preparation method and application thereof
  • Fluorescent naphthalene calix[3]arene non-porous self-adaptive crystal, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0082] The synthesis of fluorescent naphthalene ring [3] arene, the synthetic route is as follows:

[0083]

[0084] a. Synthesis of compound (1): Add 1.6g of 2,7-dihydroxynaphthalene to a dry round-bottomed double-necked flask filled with 200mL of dichloromethane as a reaction solvent, add 20mL of pyridine under nitrogen protection at 0°C, and stir 8.6 mL of trifluoromethanesulfonic anhydride was added dropwise, stirred for 2 h, and reacted at room temperature for 8 h, and the reaction progress was monitored by TLC spot plate. use CH 2 Cl 2 Extract the aqueous phase. The organic phase was concentrated in vacuo. Purification by column chromatography gave a white solid compound with a yield of 79.5% and a melting point of 62-64°C. H NMR spectrum data: 1 H NMR (500MHz, Chloroform-d): δ8.00 (d, J=9.0Hz, 2H), 7.81 (d, J=2.2Hz, 2H), 7.48 (dd, J=9.1, 2.4Hz, 2H).

[0085] b. Synthesis of fluorescent naphthalene cyclo[3]arene monomer: Take a clean and dry round-bottomed doubl...

Embodiment 2

[0090]The fluorescent naphthalene[3]arene prepared in Example 1 was recrystallized through a dichloromethane-methanol solvent system to obtain a powder crystal structure, and after being activated in a vacuum oven at 75°C for 12 hours, the fluorescent naphthalene[3]arene was obtained. Hole Adaptive Crystal. At the same time, the organic dye malachite green was prepared into a 500mL solution with a concentration of 20μM, and 12.36mg of activated fluorescent naphthalene[3]arene non-porous self-adaptive crystal was added, and the organic dye was fully shaken and vibrated at 25°C to observe the ultraviolet absorption of the organic dye. value changes. The UV-Vis absorption spectrum of the organic dye malachite green solution is measured as image 3 shown.

[0091] The adsorption process is divided into three parts: external diffusion, internal diffusion, and the combination of adsorbate molecules and adsorbent molecules. from image 3 It can be seen that the absorption value o...

Embodiment 3

[0093] The fluorescent naphthalene cyclo[3]arene non-porous self-adaptive crystal prepared in Example 1 was tested for solid UV-visible absorption spectrum and fluorescence emission spectrum, and the measured UV-visible absorption spectrum and fluorescence emission spectrum were normalized overlay spectrograms ,Such as Figure 4 shown. from Figure 4 It can be seen that the fluorescent naphthalene cyclo[3]arene nonporous adaptive crystal still exhibits significant blue light emission in the solid state due to its molecular structure containing the characteristic naphthalene group of fluorophore, which restricts the molecular motion and avoids aggregation-induced fluorescence. Quenching phenomenon, the fluorescence emission peak is about 375-415nm.

[0094] The ultraviolet-visible absorption spectrum of the guest molecule chlorophyll magnesium sodium salt is as follows: Figure 5 shown. It can be seen from the figure that the guest molecule (acceptor) has a strong absorptio...

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Abstract

The invention discloses a fluorescent naphthalene calix[3]arene non-porous self-adaptive crystal, and a preparation method and application thereof. The preparation method comprises the following steps: firstly, replacing hydroxyl in 2, 7-dihydroxynaphthalene with trifluoromethanesulfonic anhydride; then coupling with 2, 5-dimethoxyphenylboronic acid to obtain a fluorescent naphthalene calix[3]arene monomer; and finally carrying out polymerization by taking dimethoxymethane as a source of a methylene bridge to obtain the fluorescent naphthalene calix[3]arene. According to the method, the situation that paraformaldehyde is used as a methylene bridge source in a traditional synthesis method is changed, and the influence of low solubility and reactivity of paraformaldehyde in an organic medium is avoided. The fluorescent naphthalene calix[3]arene has a larger cavity structure, and the nonporous self-adaptive crystal prepared from the fluorescent naphthalene calix[3]arene not only can rapidly capture fluorescent molecule sodium magnesium chlorophyllin from water to construct an artificial light capture system, but also can capture a trace amount of large-size organic dye molecule malachite green, so that the adsorption range of the nonporous self-adaptive crystal is expanded, and the fluorescent naphthalene calix[3]arene non-porous self-adaptive crystal is a potential novel water pollutant purifier.

Description

technical field [0001] The invention belongs to the technical field of organic chemical synthesis and the field of adsorption materials, and specifically relates to a non-porous self-adaptive crystal of fluorescent naphthalene ring[3]arene, a preparation method and application thereof. Background technique [0002] Efficient design and synthesis of new macrocycles is one of the most important research aspects in supramolecular chemistry. Many macrocyclic hosts with unique structures and functionalizations have been reported in recent years, such as crown ethers, cucurbiturils, cyclodextrins, calixarenes, pillararenes, and bowtie arenes, etc. From a synthetic point of view, most supramolecular macrocycles are formed by condensation of monomers with paraformaldehyde or aliphatic aldehydes under Lewis acid-catalyzed conditions. However, paraformaldehyde, as an important reactant for the formation of methylene bridges, has low solubility and reactivity in organic media, which g...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C43/21C07C41/30C07C41/40C09K11/06B01J20/22
CPCC07C43/21C09K11/06B01J20/22C07C2603/92C07B2200/13C09K2211/1011
Inventor 唐浩黄振腾
Owner SOUTH CHINA UNIV OF TECH
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