Application of star-shaped oligomer in photochromic anti-counterfeiting

Abstract

The invention discloses an application of a star-shaped oligomer in photochromic anti-counterfeiting, and belongs to the technical field of anti-counterfeiting. The star-shaped oligomer disclosed by the invention has a double-peak fluorescence spectrum, and the triphenylamine core structure and the DASA photoresponse unit are subjected to reversible photoisomerization reaction under light stimulation, so that the absorption peak of the star-shaped oligomer in a visible light region is changed, and the displacement and the intensity of a fluorescence emission spectrum are changed, and therefore, dual-mode response of color and fluorescence is realized. And after being dissolved in a polymer solution and poured into a film, the film can be used for constructing an anti-counterfeiting product with a multi-information encryption function. The anti-counterfeiting material provided by the invention is simple and convenient to prepare, quick in response, good in repeatability and suitable for high-security anti-counterfeiting labels and information encryption systems.

Description

Technical Field

[0001] This application belongs to the field of encryption and anti-counterfeiting technology, and in particular relates to the application of a star-shaped oligomer in photochromic anti-counterfeiting. Background Technology

[0002] DASA compounds are nonlinear, including dendritic, star-shaped, and multi-branched DASA molecules. Star oligomers are macromolecules composed of several linear oligomers or arms linked together by a central structure (core). Due to their highly branched structure and unique molecular conformation, star polymers exhibit properties and functions significantly different from linear polymers. In recent years, researchers have made significant progress in controlled synthesis, precise control of arm number, and functionalization. Most star oligomers possess excellent optical properties, including high photoluminescence quantum yield in their solid-state films and very low optical loss. Furthermore, their physicochemical properties can be tuned by changing the arm length, making star oligomers highly tunable. Due to their enormous application potential in multiple disciplines, star polymers have become a research frontier in interdisciplinary fields such as materials science, chemistry, and biomedicine.

[0003] The prior art discloses a photochromic encryption system, including a carrier and an encryption information layer disposed on the carrier. The encryption information layer is formed by a combination of coating areas of four different encryption inks. However, the encryption information layer needs to be mixed and coated, the manufacturing process is complicated and difficult to industrialize, and it only reflects the color change after light exposure, and the encryption performance needs to be improved.

[0004] Therefore, applying star-shaped oligomers to photochromic anti-counterfeiting is simple to produce and achieves dual-mode anti-counterfeiting using both color and fluorescence signals, resulting in stronger encryption. This has significant research and application value. Summary of the Invention

[0005] To address the technical problems of complex processes and insufficient anti-counterfeiting capabilities in existing anti-counterfeiting systems, the primary objective of this invention is to provide an application of star-shaped oligomers in photochromic anti-counterfeiting, which is simple to manufacture and achieves dual-mode anti-counterfeiting using both color and fluorescence signals, resulting in stronger encryption.

[0006] Another object of the present invention is to provide an anti-counterfeiting product prepared from the above-mentioned star-shaped oligomer.

[0007] To achieve the above-mentioned objectives, the present invention adopts the following technical solution: This invention protects the application of a star-shaped oligomer in photochromic anti-counterfeiting, wherein the star-shaped oligomer has the following structural formula: ; Where n = 1, 2, 3, in, It can be any of the following: .

[0008] The inventors discovered that star-shaped oligomers can be used for photochromic anti-counterfeiting, achieving a dual-mode anti-counterfeiting approach involving both color and fluorescence signals. This stems from their bimodal fluorescence properties, which simultaneously undergo absorption and fluorescence signal changes under light stimulation. Specifically, when exposed to light of a specific wavelength, the conjugated triene in the DASA moiety transforms into a cyclic structure, resulting in a reversible photoisomerization reaction. This directly leads to a significant reduction in the absorption peak at approximately 590 nm in the visible light region, causing a macroscopically visible color fading or change in the material—the first, intuitive color-based anti-counterfeiting mode. Simultaneously, the star-shaped oligomers of this invention possess a core triphenylamine structure. This molecular configuration change profoundly affects the microenvironment of its luminescent cluster, altering its inherent bimodal fluorescence emission spectrum. This is typically manifested as a shift in the emission peak (e.g., from the orange-red region to the blue region) and an overall decrease in fluorescence intensity. This constitutes a second, more concealed and precise anti-counterfeiting mode that requires verification using tools such as ultraviolet lamps. These two modes, with their visible color changes and measurable fluorescence conversions, are both triggered by the same light source and do not interfere with each other. Together, they form a dual-mode anti-counterfeiting system that is highly information-dense, difficult to replicate, and easy to verify.

[0009] Preferably, n = 2 or 3.

[0010] Preferably, the star-shaped oligomer is any one of the following compounds: Formula 1 Formula 2 Formula 3 Formula 4 Formula 5 Formula 6 Formula 7.

[0011] Specifically, the star-shaped oligomer is prepared according to existing technology.

[0012] Preferably, the star-shaped oligomer is prepared by the following steps: Donor and acceptor molecules are mixed and dissolved in a dichloromethane / hexafluoroisopropanol mixed solvent. The mixture is then reacted in the dark and purified to obtain a star-shaped oligomer, wherein the molar ratio of donor to acceptor molecules is ≤1:3.

[0013] This invention also protects an anti-counterfeiting product prepared from the above-mentioned star-shaped oligomer.

[0014] This invention also protects a method for preparing the above-mentioned anti-counterfeiting product, comprising the following steps: S1. Dissolve the above-mentioned star-shaped oligomer and polymer in an organic solvent to obtain a mixed solution; S2. Pour the mixture into a polytetrafluoroethylene template to form an anti-counterfeiting product.

[0015] Preferably, the organic solvent in step S1 is tetrahydrofuran.

[0016] Preferably, the concentration of star-shaped oligomers in the mixed solution in step S1 is 1~5 g / L.

[0017] Preferably, the polymer in step S1 is selected from at least one of thermoplastic polyurethane, polycaprolactone, polymethyl methacrylate, polystyrene, SBS, and SEBS.

[0018] Preferably, the mass concentration of the polymer in the mixed solution in step S1 is 0.1~0.3 g / mL.

[0019] Compared with the prior art, the present invention has the following beneficial effects: This invention discloses the application of a star-shaped oligomer in photochromic anti-counterfeiting. The star-shaped oligomer of this invention exhibits a bimodal fluorescence spectrum. Under light stimulation, the triphenylamine core structure undergoes a reversible photoisomerization reaction with the DASA photoresponse unit, leading to changes in its absorption peak in the visible light region and shifts and intensities in its fluorescence emission spectrum, thereby achieving a dual-mode response of color and fluorescence. Dissolving it in a polymer solution and casting it into a film can be used to construct anti-counterfeiting products with multiple information encryption functions. The anti-counterfeiting material provided by this invention is simple to prepare, has a rapid response, and good repeatability, making it suitable for high-security anti-counterfeiting labels and information encryption systems. Attached Figure Description

[0020] Figure 1 The UV-Vis absorption spectrum of the star-shaped oligomer DASA under illumination; Figure 2 The fluorescence spectra of star-shaped oligomer DASA before and after irradiation; Figure 3 Images show the color and fluorescence changes of the star-shaped oligomer DASA before and after photochromic changes. Figure 4 (a) Changes in fluorescence spectrum of star-shaped oligomer DASA before and after photochromism; (b) Multiple encryption design scheme of star-shaped oligomer DASA; (c) Example diagram of multiple encryption design of star-shaped oligomer DASA. Figure 5 The 1H NMR spectrum of DASA-2 in Example 1; Figure 6 The 1H NMR spectrum of DASA-1 in Example 3; Figure 7 The 1H NMR spectrum of Example 4; Figure 8 This is the proton NMR spectrum of Comparative Example 1. Detailed Implementation

[0021] The present invention is further illustrated below with reference to specific embodiments. These embodiments are for illustrative purposes only and are not intended to limit the scope of the invention. Experimental methods in the following embodiments that do not specify specific conditions are generally performed under conventional conditions in the art or as recommended by the manufacturer; the raw materials and reagents used, unless otherwise specified, are all commercially available from the conventional market. Any non-substantial changes and substitutions made by those skilled in the art based on the present invention are within the scope of protection claimed by the present invention.

[0022] I. Experimental Methods Example 1 Synthesis of DASA-2 star oligomers:

[0023]

[0024] p-Bromoaniline (1.00 g, 5.85 mmol, 1.00 eq.) was dissolved in 50 mL of methanol solution. Subsequently, decarbonyl di-tert-butyl ester (2.60 g, 11.9 mmol, 2.03 eq.) was added and dispersed by ultrasonication. The mixture was stirred at room temperature for about 3 h to obtain an intermediate product. After rotary evaporation and washing with a large amount of n-hexane, a white powder compound 1 (1.51 g, 95.0%) was obtained.

[0025] The obtained white powder compound 2-1 (1.50 g, 5.51 mmol) was dissolved in 100 ml of tetrahydrofuran solution. Then, sodium tert-butoxide (1.24 g, 11.7 mmol, 2.12 eq.) and methyl iodide (4.00 g, 17.61 mmol, 3.20 eq.) were added to the system. After stirring the mixture at room temperature for 12 hours, the solvent was removed by rotary evaporation to obtain yellow precipitate compound 2 (1.52 g, 96.6%).

[0026] In a dry Schiller flask, the above-mentioned compound 2-2 (1.00 g, 3.51 mmol), tris(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborhexacyclopentan-2-yl)phenyl)amine (0.62 g, 0.99 mmol, 0.28 eq.), K2CO3 (9.66 g, 7.00 mmol, 2 eq.), and Pd(PPh3)4 (11.5 mg, 0.010 mmol) were added sequentially. After evacuation and argon purging three times, 10.0 mL of degassed tetrahydrofuran was injected, and the mixture was stirred at 100 °C for 8 h. Cool to room temperature, add saturated NH4Cl (5 mL), extract with EtOAc (3 × 5 mL), combine organic phases, wash with saturated brine, dry with anhydrous Na2SO4, concentrate under reduced pressure, and purify the residue by silica gel column chromatography (petroleum ether / ethyl acetate = 5:1) to give white solid 3 (0.95 g, 1.10 mmol, 31.3%).

[0027]

[0028] Compound 2-3 (0.5 g, 0.58 mmol) was dissolved in DCM, treated with excess trifluoroacetic acid, and then extracted with DCM and saturated brine. The organic layer was evaporated to dryness to give brown solid 2-4 (0.31 g, 95.4%).

[0029]

[0030] In a 10 mL flask, compounds 2-4 (100 mg, 0.18 mmol, 1.0 eq.) and S1 (110.3 mg, 0.36 mmol, 2.0 eq.) were added to 4 mL of dichloromethane (DCM). Subsequently, 1 mL of hexafluoroisopropanol (HFIP) was added and the mixture was stirred in the dark for 24 hours. After removing the solvent by rotary evaporation, the remaining solid was dissolved in 2 mL of THF and poured into 250 mL of n-hexane. The suspension was then filtered through a vacuum filter, the filtrate was removed, and the residue was washed several times with a mixture of tetrahydrofuran / n-hexane (approximately 1:60) to give a blue solid, DASA-2 (149 mg, 56.00%).

[0031] Example 2 Synthesis of DASA-3 star oligomers, n=3:

[0032]

[0033] In a dry Schiller flask, tert-butyl(4'-bromo-[1,1'-biphenyl]-4-yl)(methyl)carbamate (1.00 g, 2.75 mmol), tris(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborhexacyclopentan-2-yl)phenyl)amine (0.48 g, 0.77 mmol, 0.28 eq.), K₂CO₃ (7.59 g, 5.50 mmol, 2 eq.), and Pd(PPh₃)₄ (11.5 mg, 0.010 mmol) were added sequentially. After evacuation and purging with argon three times, 10.0 mL of degassed tetrahydrofuran was injected, and the mixture was stirred at 100 °C for 8 h. Cool to room temperature, add saturated NH4Cl (5 mL), extract with EtOAc (3 × 5 mL), combine organic phases, wash with saturated brine, dry with anhydrous Na2SO4, concentrate under reduced pressure, and purify the residue by silica gel column chromatography (petroleum ether / ethyl acetate = 5:1) to give a white solid 3-3 (0.57 g, 0.52 mmol, 68.03%).

[0034]

[0035] Compound 3-3 (0.5 g, 0.46 mmol) was dissolved in DCM, treated with excess trifluoroacetic acid, and then extracted with DCM and saturated brine. The organic layer was evaporated to dryness to give brown solid 3-4 (0.36 g, 99.3%).

[0036]

[0037] In a 10 mL flask, compounds 3-4 (100 mg, 0.13 mmol, 1.0 eq.) and S1 (79.7 mg, 0.26 mmol, 2.0 eq.) were added to 4 mL of DCM. Subsequently, 1 mL of HFIP was added and the mixture was stirred in the dark for 24 hours. After removing the solvent by rotary evaporation, the remaining solid was dissolved in 2 mL of THF and poured into 250 mL of n-hexane. The suspension was then filtered through a vacuum filter, the filtrate was removed, and the residue was washed several times with a mixture of tetrahydrofuran / n-hexane (approximately 1:60) to give a blue solid, DASA-3 (112 mg, 50.50%).

[0038] Example 3 Synthesis of DASA-1 star oligomers, n=1:

[0039]

[0040] In a 10 mL flask, compounds 1-4 (100 mg, 0.30 mmol, 1.0 eq.) and S1 (183.92 mg, 0.60 mmol, 2.0 eq.) were added to 4 mL of DCM. Subsequently, 1 mL of HFIP was added and the mixture was stirred in the dark for 24 hours. After removing the solvent by rotary evaporation, the remaining solid was dissolved in 2 mL of THF and poured into 250 mL of n-hexane. The suspension was then filtered through a vacuum filter, the filtrate was removed, and the residue was washed several times with a mixture of tetrahydrofuran / n-hexane (approximately 1:80) to give a blue solid, DASA-1 (183 mg, 48.80%).

[0041] Example 4 A DASA compound, .

[0042] The preparation method is as follows:

[0043] Step 1: The donor molecule 1,3,5-tris(4-N-methylaminophenyl)amine (25 mg, 0.076 mmol, 1 eq) and the acceptor molecule 2,2-diethyl-5-(2-furanylmethylene)-1,3-dioxane-4,6-dione (95 mg, 0.38 mmol, 5 eq) were dissolved in a mixed solvent of 3 mL dichloromethane and 0.75 mL hexafluoroisopropanol. The mixture was stirred in the dark at a certain temperature for 24 hours to obtain a crude product solution of the novel DASA compound No. 10. The molar ratio of donor molecules to acceptor molecules is 1:5; Step 2: After removing the solvent from the crude product solution of the new DASA compound No. 10 obtained in Step 1 by vacuum distillation, 20 ml of anhydrous diethyl ether was added, and the mixture was stirred for 1 hour at room temperature in the dark to obtain a purplish-black suspension. The suspension was filtered and the precipitate was collected. The precipitate was washed with diethyl ether to obtain 72 mg of black powder, which is the new DASA compound No. 10, with a yield of 88%.

[0044]

[0045] The structure of the product is obtained from the proton NMR spectrum, such as Figure 7 .

[0046] Example 5

[0047] In a 10 mL flask, compounds 2-4 (100 mg, 0.18 mmol, 1.0 eq.) and S3 (83.16 mg, 0.36 mmol, 2.0 eq.) were added to 4 mL of dichloromethane (DCM). Subsequently, 1 mL of hexafluoroisopropanol (HFIP) was added and the mixture was stirred in the dark for 24 hours. After removing the solvent by rotary evaporation, the remaining solid was dissolved in 2 mL of THF and poured into 250 mL of n-hexane. The suspension was then filtered through a vacuum filter, the filtrate was removed, and the residue was washed several times with a mixture of tetrahydrofuran / n-hexane (approximately 1:80) to give a blue solid (82.10 mg, 36.23%).

[0048] Example 6

[0049] In a 10 mL flask, compounds 2-4 (100 mg, 0.18 mmol, 1.0 eq.) and S4 (118.08 mg, 0.36 mmol, 2.0 eq.) were added to 5 mL of dichloromethane (DCM). Subsequently, 1 mL of hexafluoroisopropanol (HFIP) was added and the mixture was stirred in the dark for 24 hours. After removing the solvent by rotary evaporation, the remaining solid was dissolved in 2 mL of THF and poured into 250 mL of n-hexane. The suspension was then filtered through a vacuum filter, the filtrate was removed, and the residue was washed several times with a mixture of tetrahydrofuran / n-hexane (approximately 1:80) to give a blue solid (127 mg, 45.52%).

[0050] Example 7

[0051] In a 10 mL flask, compounds 2-4 (100 mg, 0.18 mmol, 1.0 eq.) and S4 (80.64 mg, 0.36 mmol, 2.0 eq.) were added to 5 mL of dichloromethane (DCM). Subsequently, 1 mL of hexafluoroisopropanol (HFIP) was added and the mixture was stirred in the dark for 24 hours. After removing the solvent by rotary evaporation, the remaining solid was dissolved in 2 mL of THF and poured into 250 mL of n-hexane. The suspension was then filtered through a vacuum filter, the filtrate was removed, and the residue was washed several times with a mixture of tetrahydrofuran / n-hexane (approximately 1:80) to give a brown solid (93.2 mg, 47.05%).

[0052] Example 8 - Fluorescence Experiment A solution was prepared by dissolving star-shaped oligomers and polyurethane polymers in tetrahydrofuran (THF) at a concentration of 2 g / L. The mixture was then poured into a polytetrafluoroethylene (PTFE) template. After the THF solvent evaporated, the pattern appeared bluish-purple, exhibiting bright pink fluorescence under UV light in the dark. Under white light, the pattern faded from bluish-purple to colorless, and the fluorescence intensity significantly decreased under UV light in the dark. Multiple information encryption designs were then implemented to address this issue. Comparative Example 1 A DASA compound,

[0053] The preparation method is as follows: Step 1: The donor molecule 1,3,5-tris(4-N-methylaminophenyl)benzene (30 mg, 0.076 mmol, 1 eq) and the acceptor molecule 2,2-diethyl-5-(2-furanylmethylene)-1,3-dioxane-4,6-dione (95 mg, 0.38 mmol, 5 eq) were dissolved in a mixed solvent of 3 mL dichloromethane and 0.75 mL hexafluoroisopropanol. The mixed solution was stirred in the dark at a certain temperature for 24 hours to obtain a crude product solution of the first new DASA compound. The molar ratio of donor molecules to acceptor molecules is 1:5. Step 2: After removing the solvent from the crude product solution of the new DASA compound obtained in Step 1 by vacuum distillation, 20 ml of anhydrous diethyl ether was added, and the mixture was stirred for 1 hour at room temperature in the dark to obtain a purple-red suspension. The suspension was filtered and the precipitate was collected. The precipitate was washed with diethyl ether to obtain 79 mg of purple powder, which is the new DASA compound with the first structure, with a yield of 91%.

[0054]

[0055] The structure of the product is obtained from the proton NMR spectrum, such as Figure 8 .

[0056] II. Test Indicators (1) Fading rate (s): The time it takes for the star-shaped oligomer to fade from blue-purple to colorless under white light.

[0057] III. Test Results The star-shaped oligomers provided in Examples 1-7 were used to make anti-counterfeiting products according to the method in Example 8 and fluorescence experiments were conducted. Examples 1-7 all have excellent bimodal fluorescence characteristics and photochromic behavior, which can realize dual-mode anti-counterfeiting of color and fluorescence.

[0058] Example 1 (n=2, DASA-2): Its UV-Vis absorption spectrum ( Figure 1 ) and fluorescence spectrum ( Figure 2 , Figure 4 a) It is clearly shown that under light stimulation, its absorption peak near 590 nm is significantly reduced, while the fluorescence emission peak shifts and its intensity changes. For example... Figure 3 As shown, anti-counterfeiting products made with DASA-2 exhibit a bluish-purple color and fluoresce bright pink under ultraviolet light in a dark environment. Under white light, the pattern fades from bluish-purple to colorless, and the fluorescence intensity significantly decreases under ultraviolet light in a dark environment. Multiple layers of information encryption are implemented to address this, such as... Figure 4 As shown, the polymer solution was poured into a polytetrafluoroethylene (PTFE) template with the English letter "FACT" and a PTFE template with the number "2607," respectively. After the tetrahydrofuran evaporated, the first two letters and the number were illuminated with white light as input until "FA" and "26" faded (different output signals could be obtained depending on the duration of white light illumination). Information was read using fluorescence spectroscopy. When the input information was a letter, the fluorescence peak at approximately 400-500 nm was used as the output; when the input information was a number, the full width at half maximum (FWHM) of the fluorescence peak at approximately 600-800 nm was used as the output. Figure 4 c. At this point, the correct information output by "FACT" is "(442, 442, 428, 428)", while the correct information output by "2607" is "(78, 78, 92, 92)".

[0059] Example 2 (n=3, DASA-3): The three-armed star structure endows the molecule with a higher density of functional groups and a stronger fluorescence signal. It also exhibits a distinct bimodal fluorescence response; changes in the position and intensity of the two fluorescence emission peaks were observed before and after illumination, ensuring its reliable application in a dual-mode anti-counterfeiting system.

[0060] Example 3 (n=1, DASA-1): It also produced bimodal fluorescence behavior, which can achieve dual changes in color and fluorescence, meeting the basic dual-mode anti-counterfeiting requirements.

[0061] The star-shaped oligomers prepared in Examples 4, 5, and 6 all exhibit significant bimodal fluorescence characteristics. Under light stimulation, the star-shaped oligomers of Examples 4, 5, and 6 not only undergo a visible color change (fading from blue-violet to colorless), but also show two distinct emission peaks in their fluorescence emission spectra, each corresponding to a different fluorescence signal. This bimodal fluorescence behavior enables these materials to simultaneously achieve dual-mode responses in both color and fluorescence, making them suitable for multi-layered information encryption designs.

[0062] The common key to Examples 1-7 lies in the fact that their molecular cores are all triphenylamine structures, combined with DASA photoresponse units. This specific structural design allows them to not only undergo visible color changes under light, but also to provide a second, more covert, and information-dense fluorescent anti-counterfeiting mode due to the shift and intensity changes in their inherent bimodal fluorescence spectra before and after light exposure.

[0063] In contrast, the DASA compound in Comparative Example 1, with triphenylbenzene as its core structure, although successfully synthesized and exhibiting some fluorescence, has a single-peak fluorescence emission spectrum lacking bimodal characteristics. Therefore, it cannot achieve the multi-layered information encryption based on bimodal fluorescence signal interpretation as described in this invention; it can only provide a single color change response, and its anti-counterfeiting capabilities and security are far inferior to the star-shaped oligomer of this invention.

[0064] Table 1. Decolorization rates of star-shaped oligomers in Examples 1-7

[0065] according to Figure 1 As shown in the absorption spectrum of DASA-2, it completely fades after 180 s. From the data in Table 1, it can be seen that the DASA-2 compound in Example 1 exhibits the fastest fading response, with a fading rate of only 180 seconds; the fading response rate of DASA-3 in Example 2 is slightly slower than that of DASA-2; the fading rate of DASA-1 in Example 3 is relatively slower, possibly due to its relatively simple molecular structure and weaker steric hindrance and synergistic effect of photoisomerization; Example 4, with a substituted group, has a similar fading rate to DASA-1; Examples 5-7, with substituted groups compared to DASA-2, have slightly worse fading rates than DASA-2, but the difference is not significant.

[0066] In this invention, "fading rate" is a key kinetic indicator for measuring the responsiveness of anti-counterfeiting materials. Specifically, it refers to the time required for a material to transition from a colored state (e.g., blue-violet) to a faded state (e.g., colorless) under light triggering. Generally, a faster fading rate (e.g., 180 seconds in Example 1) means a quicker anti-counterfeiting verification process. In scenarios requiring immediate verification, a rapid response can significantly improve anti-counterfeiting efficiency. However, a faster fading rate is not always better; the optimal choice depends on the specific application scenario and functional requirements. Therefore, this invention provides a series of compounds with different fading rates, allowing the selection of the most suitable star-shaped oligomer based on the specific requirements for response speed, information retention time, and operational procedures in actual applications.

[0067] Finally, it should be noted that the above embodiments are only used to illustrate the technical solutions of the present invention and are not intended to limit the scope of protection of the present invention. Although the present invention has been described in detail with reference to preferred embodiments, those skilled in the art should understand that modifications or equivalent substitutions can be made to the technical solutions of the present invention without departing from the essence and scope of the technical solutions of the present invention.

Claims

1. Use of a star oligomer in photochromic anti-counterfeiting, characterized in that, The star-shaped oligomer has a structural formula as shown in the following formula: ； wherein n = 1, 2, or 3. wherein is any one of: 。 2. Use according to claim 1, characterized in that, The n = 2 or 3.

3. Use according to claim 1, characterized in that, The star-shaped oligomer is specifically any one of the following compounds: Formula 1, Formula 2, Formula 3, Formula 4, Formula 5, Formula 6, Formula 7.

4. The use according to any one of claims 1 to 3, characterized in that, The star-shaped oligomer is prepared by the following steps: The donor molecule and the acceptor molecule are mixed and dissolved in a dichloromethane / hexafluoroisopropanol mixed solvent, and reacted in the dark to obtain the star-shaped oligomer, wherein the molar ratio of the donor molecule to the acceptor molecule is ≤ 1:

3.

5. An anti-counterfeit article, characterized by, The star-shaped oligomer is prepared by the following steps:

6. A method of producing the security article of claim 5, characterized in that, The steps include the following steps: S1. dissolving the star-shaped oligomer of any one of claims 1-4 and a polymer in an organic solvent to obtain a mixed solution; S2. pouring into a polytetrafluoroethylene mold to form an anti-counterfeiting product.

7. The method of claim 6, wherein, The organic solvent in step S1. is tetrahydrofuran.

8. The method of claim 6, wherein, The concentration of the star-shaped oligomer in the mixed solution in step S1. is 1-5 g / L.

9. The method of claim 6, wherein, The polymer in step S1. is selected from at least one of thermoplastic polyurethane, polycaprolactone, polymethyl methacrylate, polystyrene, SBS, and SEBS.

10. The method of claim 6, wherein, The mass concentration of the polymer in the mixed solution in step S1. is 0.1-0.3 g / mL.

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