Aromatic polymer material, preparation method thereof and application of aromatic polymer material as fluorescence sensor in active carbonyl compound detection

Abstract

The invention relates to an aromatic polymer material, a preparation method thereof and application of the aromatic polymer material as a fluorescence sensor in active carbonyl compound detection, and belongs to the field of fluorescence sensing. The preparation method comprises the following steps: by taking squaric acid (SA) and 1, 3, 5-tri (4-aminophenyl) benzene (TAPB) as monomers, carrying out solvothermal condensation reaction in a water-phase solvent to prepare the aromatic polymer material SA-TAPB. The polymer material presents a regular microsphere morphology and has good fluorescence performance, the invention also discloses application of the material in the field of fluorescence sensing, especially detection of active carbonyl compounds, and the material has high specific recognition capability on active carbonyl compounds such as formaldehyde (FA), glyoxal (Gly), acrolein (MGO) and the like in various analytes, and has good application prospects. High-selectivity and high-sensitivity fluorescent sensing of the compounds can be realized, and the preparation method is simple, convenient and efficient and has extremely high practicability.

Description

Technical Field

[0001] This invention belongs to the field of analytical detection technology, and relates to the preparation methods and applications of three aromatic polymer materials, especially the highly selective fluorescence detection of active carbonyl compounds by polymer materials. Background Technology

[0002] Reactive carbonyl species (RCS) are a class of highly reactive electrophilic molecules that can be generated in vivo through metabolism or ingested exogenously, participating in regulatory processes such as cell signal transduction under physiological conditions. However, when endogenous metabolic disorders or excessive exogenous input cause abnormally high concentrations of RCS (such as formaldehyde, glyoxal, and acetone aldehyde), carbonyl stress is triggered, which in turn modifies biomolecules such as proteins and nucleic acids, damaging their structure and function, and ultimately promoting the development of diseases such as diabetes, neurodegenerative diseases, cardiovascular diseases, and cancer. Therefore, developing efficient detection technologies that can accurately monitor the dynamic changes in RCS is of vital importance for elucidating related pathological mechanisms and disease prevention and treatment.

[0003] Traditional RCS detection methods, including gas chromatography (GC), radiometric methods, high-performance liquid chromatography (HPLC), colorimetric detection, Raman spectroscopy, and electrophoresis, offer high sensitivity and selectivity. However, these methods involve complex sample preparation processes that can cause irreparable damage to the sample, making real-time tracking of RCS concentrations in vivo impossible. Fluorescent probe technologies developed for detecting bioactive substances in organisms offer advantages such as simplicity, high sensitivity and selectivity, rapid identification, minimal sample damage, and real-time monitoring of the organism.

[0004] Aromatic polymers, due to the aromatic ring structures in their main or side chains, can form delocalized π-electron systems, exhibiting both excellent photoelectric properties and molecular chain "signal amplification" effects. In the field of fluorescence sensing, they demonstrate advantages such as high sensitivity, structural designability, and ease of device fabrication. Based on this, this invention combines the aforementioned properties of aromatic polymers with the specific recognition of active carbonyl compounds to construct a high-performance fluorescence sensing platform for detecting active carbonyl compounds.

[0005] Wang et al. (FoodChemistry, 2024) designed a hydrophilic-modified "on-type" fluorescent probe, Nap-FA, which uses a hydrazine group as the FA recognition site. It blocks photoinduced electron transfer and activates the fluorescence signal through a specific condensation reaction. The probe has excellent water solubility, rapid response (20s), high selectivity, 62-fold increase in fluorescence intensity, and a detection limit of 3.9μM. It also has a large Stokes shift (~120nm) and good photostability, enabling fluorescence imaging of exogenous FA in live cells, zebrafish, and plant root tissues, as well as rapid visual detection of FA in real food. Ye et al. (Chinese Chemical Letters, 2025) developed a fluorescent probe based on 8-hydrazino-boron dipyrrole methylene (OPTY). This probe generates a strong blue fluorescent hydrazone product (emission wavelength 465 nm) through a specific aldehyde-amine condensation reaction with fatty acids (FA), achieving highly selective and sensitive detection of FA (detection limit 26.5 nM). The probe was integrated into a portable sensor chip and combined with a smartphone to build an analysis platform, which was successfully applied to the rapid on-site quantitative analysis of FA in foods such as squid and tripe. El-Maghrabey et al. (Microchemical Journal, 2025) established a superselective fluorescent microplate detection method for glyoxal. The method involves the trimeric cyclization reaction of glyoxal with ammonium acetate at 75 °C to generate the fluorescent product 2,2'-biimidazole (excitation wavelength 270 nm, emission wavelength 335 nm). This method exhibits good linearity in the range of 0.05–10.0 μM, with a detection limit of 0.015 μM. It demonstrates excellent selectivity and is environmentally friendly. When applied to river water samples, the recovery rate reached 90.6%–103.8%, providing a new pathway for the rapid and accurate detection of glyoxal.

[0006] This invention provides a method for preparing an aromatic polymer material and its application in the detection of reactive carbonyl compounds. Specifically, this invention successfully prepares an aromatic polymer material, SA-TAPB, which possesses both fluorescence properties and reactive carbonyl compound responsiveness, using squaric acid and 1,3,5-tris(4-aminophenyl)benzene as raw materials. The fluorescence property of this material originates from the conjugated system in its molecular structure. Its inherent emission peak is located at 427 nm, and after the addition of formaldehyde, the emission peak blue-shifts to 400 nm. This characteristic allows it to be used to construct a ratiometric fluorescence sensing system for the accurate detection of formaldehyde. In addition, SA-TAPB also exhibits responsiveness to various reactive carbonyl compounds such as glyoxal and acrolein, enabling the detection of multiple target analytes. Summary of the Invention

[0007] To address the shortcomings of existing technologies, this invention provides an aromatic polymer material, its preparation method, and its applications. In particular, it provides a method for preparing the aromatic polymer material and its application in testing reactive carbonyl compounds. This aromatic polymer material exhibits good selectivity for reactive carbonyl compounds.

[0008] To achieve this objective, the present invention employs the following technical solution:

[0009] This invention provides an aromatic polymer material, which is a polymer formed by covalently linking squaric acid structural units and 1,3,5-tris(4-aminophenyl)benzene structural units through squaric acid amide bonds;

[0010] ;

[0011] In a first aspect, the present invention provides a method for preparing an aromatic polymer material, the method comprising:

[0012] Three aromatic polymer materials were prepared by adding squaric acid and different aromatic monomers to a solvent and then using a solvothermal method.

[0013] The material obtained in step (1) is washed with organic solvent, centrifuged, and vacuum dried to obtain the aromatic polymer material described above;

[0014] Preferably, the aromatic monomer is selected from 1,3,5-tris(4-aminophenyl)benzene;

[0015] Preferably, the molar ratio of aromatic monomer to squaric acid is (2-4):(1-3); for example, it can be 2:1, 3:2 or 1:3, etc., but it is not limited to the listed values. Other unlisted values ​​within this range are also applicable, with the optimal molar ratio being 2:3.

[0016] Preferably, the reaction in step (1) is carried out in a solvent. The solvent is deionized water;

[0017] Preferably, the monomer concentration ranges from 3.0 mg / mL to 7.0 mg / mL.

[0018] Preferably, the reaction in step (1) is carried out at 120-180°C for 24-74 hours; wherein the optimal reaction condition is 72 hours at 180°C.

[0019] Preferably, the aromatic polymer material obtained in step (1) is washed with an organic solvent and centrifuged.

[0020] Preferably, the organic washing method involves sequentially washing with N,N-dimethylformamide and ethanol.

[0021] This invention successfully prepared an aromatic polymer material, SA-TAPB, exhibiting fluorescence and responsiveness to reactive carbonyl compounds via a squaric acid and 1,3,5-tris(4-aminophenyl)benzene amidation reaction. Results showed that the fluorescence of SA-TAPB originates from the conjugated structure of the polymer material. Furthermore, as a squaric acid amidation product, the amide bonds in the SA-TAPB structure specifically bind to reactive carbonyl compounds through multiple interactions, including hydrogen bonding and nucleophilic addition. This core mechanism not only triggers molecular conformation optimization and conjugated system regulation but also directly endows SA-TAPB with a significant fluorescence response to reactive carbonyl compounds. This polymer can achieve highly sensitive detection of reactive carbonyl compounds and exhibits a low detection limit.

[0022] In a second aspect, the present invention provides the application of an aromatic polymer material according to the first aspect in fluorescence sensing.

[0023] A series of polymer materials were prepared by adjusting the synthesis conditions of the acid monomer and aromatic ligand. According to the SEM test results, when the reaction temperature is 180℃, the obtained polymer material exhibits a regular spherical shape. This means that the uniformly exposed recognition sites and high structural uniformity of SA-TAPB have higher sensitivity when applied to fluorescence sensing. The concentration and incubation time of SA-TAPB were optimized to obtain SA-TAPB with better fluorescence properties for the detection of active carbonyl compounds.

[0024] A method for detecting formaldehyde in aromatic polymer materials includes the following steps:

[0025] The sample to be tested is brought into contact with a suspension in which the aromatic polymer material is dispersed, and its fluorescence spectrum is measured at the excitation wavelength; the concentration of formaldehyde is qualitatively or quantitatively determined based on the blue shift of the fluorescence emission peak or the change in fluorescence intensity.

[0026] Preferably, the excitation wavelength is 290~305 nm; the formaldehyde causes the fluorescence emission peak of the polymer material to shift blue from around 427 nm to around 400 nm, and the fluorescence intensity is enhanced.

[0027] Compared with the prior art, the present invention has the following beneficial effects:

[0028] The aromatic polymer SA-TAPB described in this invention is suitable for the selective detection of reactive carbonyl compounds in real samples such as food. It can achieve responses to analytes such as formaldehyde, glyoxal, and acrolein, especially exhibiting rapid response and specificity for formaldehyde. The preparation method is simple, easy to implement, and highly efficient. This fluorescence detection method not only has high specificity for reactive carbonyl compounds but also demonstrates excellent anti-interference performance against other coexisting interfering substances, and has a low detection limit. Attached Figure Description

[0029] Figure 1 The fluorescence excitation and emission spectra of SA-TAPB prepared in Example 1 are shown.

[0030] Figure 2 The fluorescence emission spectra of SA-TAPB and its organic ligands (λ) ex =298nm);

[0031] Figure 3 SEM images of SA-TAPB under different synthetic conditions;

[0032] Figure 4 The fluorescence emission spectra (λ) of SA-TAPB, SA-TAPT, and SA-TAPA ex =298nm);

[0033] Figure 5 Fluorescence intensities at different concentrations of SA-TAPB;

[0034] Figure 6 The graph shows the changes in fluorescence intensity of SA-TAPB after the addition of FA at different times;

[0035] Figure 7 For SA-TAPB in 10 -2 Fluorescence intensity of M in the presence of different analytes;

[0036] Figure 8 Ratio fluorescence I of SA-TAPB 400 / I 427 Linear relationship with FA concentration;

[0037] Figure 9 Fluorescence emission spectra of SA-TAPB with different concentrations of FA added

[0038] Figure 10 The fluorescence emission spectra of SA-TAPB in response to other active carbonyl compounds;

[0039] Figure 11 PXRD pattern of SA-TAPB;

[0040] Figure 12 The FI-IR spectrum of SA-TAPB;

[0041] Figure 13 XPS spectra of SA-TAPB before and after adding FA;

[0042] Figure 14 Excitation spectra of SA-TAPB before and after the addition of FA;

[0043] Figure 15This is a schematic diagram of the synthesized SA-TAPB structure.

[0044] Specific Implementation Scheme

[0045] Example 1:

[0046] This embodiment provides a method for preparing an aromatic polymer material, as follows:

[0047] Accurately weigh 34 mg of squaric acid and 70 mg of 1,3,5-tris(4-aminophenyl)benzene in a molar ratio of 3:2 and disperse them in 20 mL of deionized water to form a suspension. Then, transfer the suspension to a 25 mL stainless steel autoclave lined with polytetrafluoroethylene (PTFE), seal it, and heat it in an oven at 180 °C for 72 h. After the product has cooled naturally to room temperature, it is removed for further processing. The sample after the reaction is a yellow precipitate; it is washed sequentially with N,N-dimethylformamide and ethanol until the filtrate is colorless. Then, it is dried in a vacuum oven at 70 °C for 24 h. The obtained product is an SA-TAPB polymer.

[0048] Excitation and emission spectra:

[0049] The excitation and emission spectra of the COF material prepared in Example 1 are as follows: Figure 1 As shown in the figure, the optimal excitation wavelength for this COF material is 298 nm, and 298 nm was selected as the excitation wavelength in subsequent tests.

[0050] The powder X-ray diffraction pattern of the aromatic polymer material prepared in Example 1 is as follows: Figure 11 As shown, the XRD pattern of SA-TAPB exhibits typical amorphous characteristics—diffraction peaks are concentrated at 2θ≈20° and show a broadened and diffuse morphology, which is directly related to the structural characteristics of this polymer with random stacking of molecular chains and lack of long-range order.

[0051] The Fourier transform infrared spectrum of the aromatic polymer material prepared in Example 1 is as follows: Figure 12 As shown. The FT-IR spectra of SA and TAPB monomers show a peak at 1500 cm⁻¹. -1 The C=O stretching vibration peak at 3500 cm⁻¹ is similar to that at 3500 cm⁻¹. -1 The -NH2 bending vibration peak at 1500 cm⁻¹. After the reaction, the -NH2 peak of TAPB in the SA-TAPB spectrum completely disappeared, and the peak disappeared at 1500 cm⁻¹. -1 The characteristic CN absorption peak of the squaric acid amide structure appeared nearby, and the C=O peak shape of SA was reconstructed. The rise and fall of the above functional group signals and the formation of CN confirm that the carbonyl group of SA and the amino group of TAPB underwent a squaric acid amidation reaction, and SA-TAPB was successfully prepared.

[0052] Example 2:

[0053] This embodiment provides a method for preparing an aromatic polymer material, as follows:

[0054] Accurately weigh 34 mg of squaric acid and 70 mg of 1,3,5-tris(4-aminophenyl)benzene in a molar ratio of 3:2 and disperse them in 20 mL of deionized water to form a suspension. Then, transfer the suspension to a 25 mL stainless steel autoclave lined with polytetrafluoroethylene (PTFE), seal it, and heat it in an oven at 160 °C for 72 h. After the product has cooled naturally to room temperature, it is removed for further processing. The sample after the reaction is a yellow precipitate; it is washed sequentially with N,N-dimethylformamide and ethanol until the filtrate is colorless and almost neutral. Then, it is dried in a vacuum oven at 70 °C for one day. The resulting product is an SA-TAPB polymer.

[0055] Example 3:

[0056] This embodiment provides a method for preparing an aromatic polymer material, as follows:

[0057] Accurately weigh 34 mg of squaric acid and 70 mg of 1,3,5-tris(4-aminophenyl)benzene in a molar ratio of 3:2 and disperse them in 20 mL of deionized water to form a suspension. Then, transfer the suspension to a 25 mL stainless steel autoclave lined with polytetrafluoroethylene (PTFE), seal it, and heat it in an oven at 140 °C for 72 h. After the product has cooled naturally to room temperature, it is removed for further processing. The sample after the reaction is a yellow precipitate; it is washed sequentially with N,N-dimethylformamide and ethanol until the filtrate is colorless and almost neutral. Then, it is dried in a vacuum oven at 70 °C for one day. The resulting product is an SA-TAPB polymer.

[0058] Comparative Example 1:

[0059] This comparative example provides a method for preparing an aromatic polymer material, as follows:

[0060] Accurately weigh 34 mg of squaric acid and 70.5 mg of 2,4,6-tris(4-aminophenyl)-1,3,5-triazine in a molar ratio of 3:2 and disperse them in 20 mL of deionized water to form a suspension. Then, transfer the suspension to a 25 mL stainless steel autoclave lined with polytetrafluoroethylene (PTFE), seal it, and heat it in an oven at 180 °C for 72 h. After the product cools naturally to room temperature, it is removed for further processing. The sample after the reaction is a yellow precipitate; it is washed sequentially with N,N-dimethylformamide and ethanol until the filtrate is colorless and almost neutral. Then, it is dried in a vacuum oven at 70 °C for one day. The resulting product is the SA-TAPT polymer.

[0061] Comparative Example 2:

[0062] This comparative example provides a method for preparing an aromatic polymer material, as follows:

[0063] Accurately weigh 34 mg of squaric acid and 73 mg of tris(4-aminophenyl)amine in a molar ratio of 3:2 and disperse them in 20 mL of deionized water to form a suspension. Then, transfer the suspension to a 25 mL stainless steel autoclave lined with polytetrafluoroethylene (PTFE), seal it, and heat it in an oven at 180 °C for 72 h. After the product has cooled naturally to room temperature, it is removed for further processing. The sample after the reaction is a yellow precipitate; it is washed sequentially with N,N-dimethylformamide and ethanol until the filtrate is colorless and almost neutral. Then, it is dried in a vacuum oven at 70 °C for one day. The resulting product is an SA-TAPA polymer.

[0064] Comparative Example 3:

[0065] This comparative example provides a method for preparing an aromatic polymer material, as follows:

[0066] Accurately weigh 34 mg of squaric acid and 70 mg of 1,3,5-tris(4-aminophenyl)benzene in a molar ratio of 3:2 and disperse them in 20 mL of toluene / n-butanol to form a suspension. The suspension is then transferred to a 25 mL stainless steel autoclave lined with polytetrafluoroethylene (PTFE), sealed, and heated in an oven at 180 °C for 72 h. The product is allowed to cool naturally to room temperature before further processing. The resulting sample is a yellow precipitate; it is washed sequentially with N,N-dimethylformamide and ethanol until the filtrate is colorless and almost neutral. It is then dried in a vacuum oven at 70 °C for one day. The obtained product is an SA-TAPB polymer.

[0067] The products obtained under different reaction temperatures and solvent systems were characterized using scanning electron microscopy (SEM), and the results are as follows: Figure 3 As shown. Figure 3 As can be seen, in Example 3, well-dispersed and smooth-surfaced regular microspheres were obtained in water. Comparing the morphology of other regular microspheres prepared in an aqueous system at 140°C in toluene / n-butanol with Comparative Example 3, it can be seen that the products obtained in organic solvents have disordered and irregular morphologies, containing a mixture of fibrous and irregular aggregates.

[0068] Example 4:

[0069] Fluorescence detection of different polymers:

[0070] Figure 4The fluorescence emission spectra of Example 1 SA-TAPB, Comparative Example 1 SA-TAPA, and Comparative Example 2 SA-TAPA are shown. The excitation wavelength for all three polymers was 298 nm. As can be seen from the figure, SA-TAPB exhibited the strongest fluorescence intensity at 298 nm excitation. The optimal fluorescence intensity of SA-TAPB is likely due to its highly rigid and symmetrical pure hydrocarbon structure, which effectively suppresses non-radiative transitions. In contrast, SA-TAPA and SA-TAPT, due to the presence of nitrogen atoms, are prone to intramolecular charge transfer or promote intersystem crossing, leading to fluorescence quenching. Only SA-TAPB showed a fluorescence response to formaldehyde (FA). This is primarily due to the tridentate rigid benzene ring structure of the TAPB monomer, which ensures stable and uniform NH sites on the polymer amide bond and a complete conjugated system, enabling a strong and specific interaction with formaldehyde and triggering fluorescence changes. Conversely, the non-planar structure of SA-TAPA has significant steric hindrance, and the strongly electron-withdrawing triazine ring of SA-TAPT weakens NH activity. Both of these factors result in the failure of binding with formaldehyde and the inability of the conjugated system to produce a response, thus resulting in no fluorescence signal.

[0071] Example 5:

[0072] Optimal concentration detection:

[0073] Figure 5 The fluorescence intensity of SA-TAPB at different concentrations is shown in Example 1. A 1 mg / mL SA-TAPB suspension was first prepared, and then diluted to prepare SA-TAPB suspensions ranging from 0.2 to 0.8 mg / mL. Based on the fluorescence emission spectra of SA-TAPB at different concentrations, it was found that the fluorescence intensity first increased and then decreased with increasing concentration. This result may be due to the concentration quenching effect caused by increasing the concentration of the polymer material. Therefore, the fluorescence intensity was optimal at an SA-TAPB concentration of 0.3 mg / mL, and subsequent experiments were conducted at this concentration.

[0074] Example 6:

[0075] Time stability test:

[0076] The polymer material obtained in Example 1 was incubated for different time periods, specifically: first, a 0.3 mg / mL SA-TAPB suspension was prepared, and then 10 mg / mL of the solution was added. -2 After MFA, allow it to stand to allow the FA reaction to complete.

[0077] The fluorescence stability of the polymer material prepared in Example 1 at different incubation times is as follows: Figure 6 As shown in the figure. It can be seen from the figure that adding 10... -2 After MFA, the fluorescence intensity tended to stabilize after 10 minutes of incubation, and remained essentially unchanged between 10 and 60 minutes. Therefore, subsequent experiments will perform fluorescence intensity detection after 10 minutes of incubation.

[0078] Example 7:

[0079] Selectivity and anti-interference testing: The specific methods for selectivity and anti-interference testing are as follows:

[0080] Preparation of SA-TAPB suspension: First, prepare a 1 mg / mL SA-TAPB suspension, and then dilute it to prepare a 0.3 mg / mL SA-TAPB suspension.

[0081] Selectivity assay: A series of analytes, including toluene (ToL), xylene (XyL), formaldehyde (FA), acetaldehyde (ACE), ammonia (AW), triethylamine (TEA), methanol (MeOH), acetone (AcE), and formic acid (HCOOH), were added to a 0.3 mg / mL SA-TAPB suspension to bring the analyte concentration in the suspension to 10. -2 M.

[0082] Anti-interference test: Add a FA-containing solution to a 0.3 mg / mL SA-TAPB suspension to make the FA concentration in the suspension 10. -2 M, then add ToL, XyL, ACE, AW, TEA, MeOH, AcE, and HCOOH respectively, keeping the concentration at 10. -2 M.

[0083] The SA-TAPB material prepared in Example 1 was subjected to 10 -2 Fluorescence intensity of M in the presence of different analytes, such as Figure 7 As shown. A series of 10 ppm were added to the SA-TAPB suspension. -2 The analytes for M included ToL, XyL, FA, ACE, AW, TEA, MeOH, AcE, and HCOOH. Experimental results showed that only FA exhibited ratiometric fluorescence enhancement, while the effects of other analytes on SA-TAPB fluorescence were negligible. The addition of FA did not affect the fluorescence enhancement effect, confirming its excellent detection selectivity and anti-interference capability.

[0084] Example 8:

[0085] Detection limit and linear range test:

[0086] A 0.3 mg / mL SA-TAPB suspension was prepared, and the fluorescence intensity of the SA-TAPB blank was measured. The instrument signal-to-noise ratio was calculated for LOD calculation. A series of FA solutions of different concentrations were added to the SA-TAPB suspension to maintain the FA concentration at 10. -6 ~10 -2 Fluorescence testing was performed within the M range.

[0087] The fluorescence enhancement factor I of the SA-TAPB material prepared in Example 1 400 / I 427 The linear relationship with FA concentration is as follows: Figure 8 As shown. Figure 9 The results showed that as the FA concentration increased, the fluorescence of SA-TAPB gradually increased, and the emission peak gradually blue-shifted from the original 427 nm to 400 nm. Figure 8 It can be seen that the fluorescence enhancement factor I 400 / I 427 With FA concentration at 10 -2 ~10 -6 The LOD showed a linear relationship within the M range, with a value of 1.58 μM, indicating that SA-TAPB can detect FA rapidly, sensitively, and selectively.

[0088] Example 9:

[0089] Detection of different reactive carbonyl compounds:

[0090] Prepare a 0.3 mg / mL SA-TAPB suspension, then add benzaldehyde (BzH), glyoxal (Gly), acetone aldehyde (MGO), and acrolein (ACR) separately for fluorescence detection, ensuring the concentration after addition is 10. -2 M.

[0091] The fluorescence detection of SA-TAPB material prepared in Example 1 for different carbonyl active compounds is as follows: Figure 10 As shown in the figure, SA-TAPB exhibits enhanced fluorescence for glyoxal and quenched fluorescence for benzaldehyde, acetone aldehyde, and acrolein. This indicates that SA-TAPB can be used for the detection of various reactive carbonyl compounds.

[0092] Example 10:

[0093] X-ray photoelectron spectroscopy:

[0094] The X-ray photoelectron spectrum of the SA-TAPB material prepared in Example 1 is as follows: Figure 13 As shown in the figure, a comparison of the XPS spectra of SA-TAPB before and after the detection of FA revealed significant changes in the binding energies of both O1s and N1s. Specifically, the O1s binding energy shifted from 531.5 eV and 533.6 eV to 531.9 eV and 533.7 eV, respectively, while the N1s binding energy decreased from 400.5 eV to 400.27 eV. This result indicates an interaction between FA and SA-TAPB, suggesting that FA may perturb the excited-state energy levels by altering the local microenvironment or electronic structure of the polymer chromophores. Further comparison of the excitation spectra of SA-TAPB before and after the addition of FA... Figure 14The observation of a redshift of approximately 10 nm in the excitation wavelength confirmed the above inference, indicating that the introduction of FA does indeed affect the electronic structure and optical properties of SA-TAPB.

[0095] The above description is only a preferred embodiment of the present invention. It should be noted that several improvements and extensions can be made without departing from the principle of the present invention, and these improvements and extensions should also be considered within the scope of protection of the present invention.

Claims

1. An aromatic polymer material, characterized in that: The aromatic polymer material is a polymer formed by covalently linking squaric acid structural units and 1,3,5-tris(4-aminophenyl)benzene structural units through squaric acid amide bonds.

2. The aromatic polymer material according to claim 1, characterized in that: The aromatic polymer material is composed of the structural units shown: 。 3. The method for preparing the aromatic polymer material according to claim 1, comprising the following steps: (1) Add squaric acid and 1,3,5-tris(4-aminophenyl)benzene to a solvent and mix well to obtain a precursor suspension; (2) Place the suspension in a sealed container and carry out a solvothermal reaction under heating conditions. After the reaction is completed, cool it to room temperature. (3) The obtained product is washed and dried to obtain the aromatic polymer material.

4. The method for preparing the aromatic polymer material according to claim 3, characterized in that, The solvent in step (1) is deionized water; the molar ratio of the squaric acid to 1,3,5-tris(4-aminophenyl)benzene is (2-4):(1-3).

5. The method for preparing the aromatic polymer material according to claim 3, characterized in that, The reaction temperature in step (2) is 120~180℃ and the reaction time is 24~74h.

6. The application of the aromatic polymer material according to claim 1 in the detection of active carbonyl compounds.

7. The application according to claim 6, characterized in that, The active carbonyl compound is selected from formaldehyde, glyoxal, benzaldehyde, acetone aldehyde, or acrolein.

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