CN-122011368-A - Aromatic polymer material, preparation method thereof and application of aromatic polymer material serving as fluorescent sensor in detection of active carbonyl compounds

Abstract

The invention relates to an aromatic polymer material, a preparation method thereof and application of the aromatic polymer material serving as a fluorescence sensor in detection of active carbonyl compounds, and belongs to the field of fluorescence sensing. The preparation method comprises the steps of taking Squaric Acid (SA) and 1,3, 5-tri (4-aminophenyl) benzene (TAPB) as monomers, and carrying out solvolysis reaction in an aqueous phase solvent to obtain the aromatic polymer material SA-TAPB. The polymer material presents regular microsphere morphology and has good fluorescence performance, the invention also discloses application of the material in the field of fluorescence sensing, in particular to detection of active carbonyl compounds, and in various analytes, the polymer material has high specific recognition capability on the active carbonyl compounds such as Formaldehyde (FA), glyoxal (Gly), acrolein (MGO) and the like, can realize high-selectivity and high-sensitivity fluorescence sensing of the compounds, and has simple, convenient and efficient preparation method and extremely strong practicability.

Inventors

• WANG JINMIN
• ZHENG QIAN
• QIN YONG
• TAO YONGXIN
• LI SHAN
• WANG YUAN

Assignees

• 常州大学

Dates

Publication Date

20260512

Application Date

20260325

Claims (7)

1. 1. An aromatic polymer material is characterized by being a polymer formed by covalently connecting a squaric acid structural unit and a1, 3, 5-tri (4-aminophenyl) benzene structural unit through a squaric acid amide bond.
2. 2. The aromatic polymer material according to claim 1, wherein the aromatic polymer material is composed of the structural units shown in: 。
3. 3. the method for preparing an aromatic polymer material according to claim 1, comprising the steps of: (1) Adding squaric acid and 1,3, 5-tri (4-aminophenyl) benzene into a solvent, and uniformly mixing to obtain a precursor suspension; (2) Placing the suspension in a closed container, performing solvothermal reaction under a heating condition, and cooling to room temperature after the reaction is finished; (3) And washing and drying the obtained product to obtain the aromatic polymer material.
4. 4. The method of producing an aromatic polymer material according to claim 3, wherein the solvent in the step (1) is deionized water, and the molar ratio of the squaraine to 1,3, 5-tris (4-aminophenyl) benzene is (2-4): 1-3.
5. 5. The method of producing an aromatic polymer material according to claim 3, wherein the reaction temperature under the heating condition in the step (2) is 120 to 180 ℃ and the reaction time is 24 to 74 hours.
6. 6. Use of an aromatic polymeric material according to claim 1 for detecting reactive carbonyl compounds.
7. 7. The use according to claim 6, wherein the reactive carbonyl compound is selected from formaldehyde, glyoxal, benzaldehyde, methylglyoxal or acrolein.

Description

Aromatic polymer material, preparation method thereof and application of aromatic polymer material serving as fluorescent sensor in detection of active carbonyl compounds Technical Field The invention belongs to the technical field of analysis and detection, relates to a preparation method and application of three aromatic polymer materials, and particularly relates to high-selectivity fluorescence detection of a polymer material on an active carbonyl compound. Background The active carbonyl compounds (ReactiveCarbonylSpecies, RCS) are high-activity electrophilic molecules which can be metabolized in vivo or taken in through exogenous routes and participate in the regulation and control processes of cell signal transduction and the like under physiological conditions. However, when the concentration of RCS (such as formaldehyde, glyoxal, methylglyoxal) is abnormally increased due to endogenous metabolic disorder or exogenous input, carbonyl stress is triggered, so that biological macromolecules such as protein, nucleic acid and the like are modified, the structure and the function of the biological macromolecules are damaged, and diseases such as diabetes, neurodegenerative diseases, cardiovascular diseases, cancers and the like are finally promoted. Therefore, the development of a high-efficiency detection technology capable of accurately monitoring the dynamic change of RCS has important significance for elucidating relevant pathological mechanisms and preventing and treating diseases. Traditional RCS detection methods, including Gas Chromatography (GC), radiation method, high Performance Liquid Chromatography (HPLC), colorimetric detection, raman spectroscopy and electrophoresis, can provide higher sensitivity and selectivity, but the production process of the sample is complex, and irreparable damage is caused to the sample in the sample preparation process, so that real-time tracking of the in-vivo RCS concentration cannot be realized. The fluorescent probe technology developed for detecting the active substances in the organisms has the advantages of simplicity, high sensitivity and selectivity, high recognition speed, minimum damage to the samples, real-time monitoring of the organisms and the like. The aromatic polymer can form a delocalized pi electron system due to the aromatic ring structure in the main chain or the side chain of the aromatic polymer, has excellent photoelectric characteristics and a molecular chain signal amplification effect, and has the advantages of high sensitivity, designable structure, easiness in device formation and the like in the field of fluorescence sensing. Based on this, the present invention constructs a high performance fluorescent sensing platform for detecting reactive carbonyl compounds by combining the above-described characteristics of aromatic polymers with specific recognition of reactive carbonyl compounds. Wang et al (FoodChemistry, 2024) designed an open-type fluorescent probe Nap-FA modified by hydrophilic groups, and the hydrazine groups are taken as FA recognition sites, and the photo-induced electron transfer is blocked and fluorescent signals are activated by specific condensation reaction, so that the probe has the advantages of excellent water solubility, quick response (20 s), high selectivity, 62 times of fluorescence intensity enhancement, 3.9 mu M detection limit, large Stokes displacement (120 nm) and good light stability, and can realize fluorescent imaging of exogenous FAs in living cells, zebra fish and plant root tissues and quick visual detection of FAs in real foods. Ye et al (CHINESECHEMICALLETTERS, 2025) develop a fluorescent probe based on 8-hydrazino-boron dipyrromethene (OPTY), and generate a strong blue fluorescent hydrazone product (emission wavelength 465 nM) through a specific aldoamine condensation reaction with FA, so that high-selectivity and high-sensitivity detection (detection limit 26.5 nM) of the FA is realized, the fluorescent probe is integrated into a portable sensing chip and combined with a smart phone to construct an analysis platform, and the fluorescent probe is successfully applied to on-site rapid quantitative analysis of the FA in squid, cattle tripe and other foods. The super-selective fluorescence microplate detection method of glyoxal is established by El-Maghrabey et al (MicrochemicalJournal, 2025), and fluorescent product 2,2' -biimidazole (excitation wavelength 270nm, emission wavelength 335 nm) is generated by trimerization cyclization reaction of glyoxal and ammonium acetate at 75 ℃, and the method has good linearity within the range of 0.05-10.0 mu M, has a detection limit of 0.015 mu M, has excellent selectivity and is environment-friendly, is applied to river water sample detection recovery rate of 90.6-103.8%, and provides a new path for rapid and accurate detection of glyoxal. The invention provides a preparation method of an aromatic polymer material and application thereof in detection of acti