A cumin aldehyde-based rhodotypos molecule top and its preparation method and application in decolorized asphalt slurry

Abstract

The application provides a cumin aldehyde-based rhodotoxin molecular top and a preparation method and application in decolorized asphalt slurry, and belongs to the technical field of industrial analysis and detection. The cumin aldehyde-based rhodotoxin molecular top is prepared from cumin aldehyde and rhodotoxin through directional coupling reaction, and the unique structure endows the cumin aldehyde-based rhodotoxin molecular top with excellent detection advantages: taking the flavone nucleus of rhodotoxin as a'stator', a stable molecular skeleton is provided, the cumin aldehyde side chain and the active functional group constitute a freely rotatable 'rotor' unit, the rotation freedom of the rotor can directly respond to the change of the micro-region viscosity, and the pi-conjugated network formed by the coupling of the two can realize the efficient conversion of micro-resistance to identifiable light signals. The cumin aldehyde-based rhodotoxin molecular top has the advantages of good natural product-based compatibility, in-situ non-disturbance and small sample consumption, can accurately quantify the micro-region viscosity heterogeneity of the decolorized asphalt slurry, and provides molecular-level basis for product grade definition and formula optimization of the decolorized asphalt slurry.

Description

Technical Field

[0001] This invention relates to the field of industrial analysis and testing technology, and in particular to a cuminyl rhododendron molecular gyroscope, its preparation method, and its application in decolorized asphalt slurry. Background Technology

[0002] Decolorized asphalt slurry is a type of light-colored slurry material composed primarily of decolorized asphalt or light-colored hydrogenated resin as the main binder, supplemented with water / environmentally friendly solvents, light-colored emulsifiers, tackifying resins, and anti-yellowing additives. It is mainly used in colored road paving, municipal landscape walkways, bridge deck waterproofing bonding layers, colored maintenance of old road surfaces, and colored road repair. It combines adhesion, waterproofing, and aesthetics. Its application performance, construction adaptability, and product durability all directly depend on the system's micro-area viscosity characteristics. Different application scenarios have significantly different viscosity requirements. For example, low viscosity is needed for colored road spraying to ensure leveling, while medium to high viscosity is required for bridge deck waterproofing bonding layers to improve bonding strength. This specific scenario-based requirement necessitates precise molecular-level monitoring of the micro-area viscosity of decolorized asphalt slurry.

[0003] Precise control and accurate characterization of the micro-area viscosity of decolorized asphalt slurry are key to driving the industry towards refinement and high value. Currently, commercially available decolorized asphalt slurry exhibits significant heterogeneity in micro-area viscosity due to variations in refining processes and component ratios, resulting in differences in the dispersion states of light-colored binders, emulsifiers, and additives within the system. Existing viscosity measurement tools (such as rotational viscometers and falling ball viscometers) can only characterize the average viscosity of the bulk system. This requires large sample volumes, easily disturbs the microscopic dispersion structure of the slurry during measurement, and fails to capture micro-area viscosity differences caused by uneven component distribution. Furthermore, they lack sensitivity in the low viscosity range and are prone to detection errors caused by the shear thinning effect of pseudoplastic fluids during measurement. Consequently, they cannot achieve precise in-situ characterization at the molecular level, failing to meet the practical needs of refined quality control and scenario-specific adaptation for decolorized asphalt slurry.

[0004] Currently, there are few functional molecular detection tools based on the reconstruction of natural products that can be adapted to the composite system of decolorized asphalt slurry. There is an urgent need to develop a molecular-level detection tool that combines compatibility and accuracy to help the high-quality development of the decolorized asphalt slurry industry. Summary of the Invention

[0005] The purpose of this invention is to provide a cumin-based rhododendron molecular gyroscope, its preparation method, and its application in decolorized asphalt slurry. The cumin-based rhododendron molecular gyroscope can accurately quantify the differences in micro-area fluid resistance of slurries of different viscosity grades through the difference in light signal intensity, thereby achieving rapid qualitative screening and grade differentiation of product consistency.

[0006] To achieve the above-mentioned objectives, the present invention provides the following technical solution: This invention provides a cucurbitacin-based azadirachtin molecular gyroscope having the structure shown in Formula I: Formula I.

[0007] This invention provides a method for preparing the above-mentioned cuminyl rhodopsin molecular gyroscope, comprising the following steps: A solution of calciferaldehyde, an organic base solution, and azadirachtin solution were mixed and subjected to a dehydration coupling reaction to obtain a calciferaldehyde-based azadirachtin molecular gyroscope.

[0008] Preferably, the cuminaldehyde in the cuminaldehyde solution is 4-isopropylbenzaldehyde, and the solvent in the cuminaldehyde solution includes one or more of ethanol, methanol, dimethyl sulfoxide, acetonitrile, acetone and N,N-dimethylformamide; The concentration of the calciform solution is 1~5 mol / L.

[0009] Preferably, the organic base in the organic base solution includes one or more of trimethylamine, N,N-diisopropylethylamine, pyridine, 4-diethylaminopyridine, imidazole, 4-dimethylaminopyridine, N,N,N',N'-tetramethylethylenediamine, and triethylamine. The solvent in the organic base solution is a mixed solution of an alcohol solvent and an organic solvent in a volume ratio of 1 to 5:1. The alcohol solvent includes methanol or ethanol, and the organic solvent includes one or more of acetone, acetonitrile, tetrahydrofuran, N,N-dimethylformamide, dimethyl sulfoxide, and ethyl acetate. The concentration of the organic base solution is 1~8 mol / L.

[0010] Preferably, the rhododendronin in the rhododendronin solution is 5,7-dihydroxy-2-(4-hydroxyphenyl)-6,8-dimethyl-2,3-dihydrobenzopyran-4-one, and the solvent in the rhododendronin solution includes one or more of ethanol, methanol, ethylene glycol, 1,2-propanediol and 1,3-propanediol; During the preparation of the rhododendron solution, continuous nitrogen blowing is carried out at a rate of 1-3 L / min, the mixing temperature is 30-50℃, the stirring rate is 500-1200 rpm, and the time is 0.6-1.5 h. The concentration of the rhododendron extract solution is 1~3 mol / L.

[0011] Preferably, the molar ratio of the cuminaldehyde, the rhododendronin and the organic base is 1~5:1:1~8.

[0012] Preferably, the temperature of the dehydration coupling reaction is 80~120℃, the stirring rate is 1500~2500 rpm, the nitrogen blowing rate is 3~6 L / min, and the time is 2~6 h.

[0013] This invention provides the application of the above-mentioned cumin-based rhododendron molecular gyroscope or the cumin-based rhododendron molecular gyroscope prepared by the above preparation method in decolorized asphalt slurry. The application method includes the following steps: mixing the cumin-based rhododendron molecular gyroscope with an organic solvent, mixing the resulting cumin-based rhododendron molecular gyroscope solution with decolorized asphalt slurry, measuring the light signal intensity, and obtaining the viscosity of the decolorized asphalt slurry based on the correspondence between light signal intensity and viscosity.

[0014] Preferably, the organic solvent includes ethanol, toluene, cyclohexane, N-methylpyrrolidone, or ethyl acetate.

[0015] Preferably, the concentration of the cucurbitacin molecular gyroscope solution is 10~100 μmol / L; The excitation wavelength for the optical signal intensity measurement is 300~500 nm.

[0016] The beneficial effects of this invention are: This invention, a cucurbitacin-based molecular gyroscope, utilizes a unique stator-rotor synergistic molecular configuration and a continuously extending π-conjugated framework to form a freely rotating, dynamically responsive structure. It can accurately sense changes in microfluidic resistance caused by colloidal components and thickening fillers within decolorized asphalt slurry, exhibiting a clear structure-activity relationship and strong sensing specificity. The stable polycyclic aromatic ring structure within the molecular framework endows it with excellent environmental adaptability, allowing it to remain stably present in the complex polar system of decolorized asphalt slurry for extended periods. Its chemical structure demonstrates outstanding resistance to matrix interference. This molecular gyroscope combines a large Stokes shift, high fluorescence signal-to-noise ratio, strong visual recognition effect, and long-term photostability. It effectively shields the background signal interference from the asphalt slurry's own color, emulsifiers, and organic additives. Simultaneously, it possesses ultra-high viscosity response sensitivity and an extremely low detection limit, accurately distinguishing subtle viscosity differences between different grades of decolorized asphalt slurry within the 300-900 cP range. The spectral signal is stable, the response pattern is clear, and its comprehensive photochemical performance and environmental stability are significant advantages.

[0017] DHBIC serves as an in-situ, non-destructive molecular detection tool, perfectly solving the challenge of detecting pseudoplastic fluids in decolorized asphalt slurry. Due to the unique microscopic network structure formed by the interweaving of colloidal particles and functional additives, traditional rotational viscosity testing methods easily disrupt the original microstructure of the system, leading to data bias and failing to accurately reflect the micro-region viscosity distribution characteristics. This molecular gyroscope, requiring no external shearing or system disturbance, enables in-situ real-time monitoring under static conditions, completely preserving the original microstructure of the decolorized asphalt slurry. It accurately quantifies the micro-region viscosity heterogeneity of slurries with different refining processes and formulation ratios, providing reliable molecular-level data support for product grading, production process optimization, and storage stability evaluation. This detection technology is simple to operate and widely applicable, comprehensively serving the quality control of decolorized asphalt slurry in various scenarios such as colored pavement paving, bridge deck waterproofing bonding, and road maintenance. It effectively fills the technological gap in molecular detection of micro-region viscosity in asphalt slurry, and has significant practical implications for promoting the refined control and high-value upgrading of decolorized asphalt materials, with broad prospects for industrial application. Attached Figure Description

[0018] Figure 1 This is a schematic diagram illustrating the mechanism of the calcinyl argentin molecular gyroscope in this invention for detecting the micro-area viscosity of decolorized asphalt slurry; Figure 2 This is the high-resolution mass spectrum of the cyclohexane alkyl cyclohexane molecular gyroscope in Example 1; Figure 3 The nuclear magnetic resonance spectrum of the calcinyl rhododendron molecular gyroscope of Example 1 is shown below. Figure 4 The spectra of the cucurbitacin molecular gyroscope of Example 1 in glycerol solutions with volume fractions of 0%, 10%, 30%, 50%, 70%, and 99% are shown. Figure 5 This is a linear fitting graph showing the relationship between fluorescence intensity and viscosity of the cucurbitacin molecular gyroscope from Example 1. Figure 6 The image shows the Stokes displacement test diagram of the calciferol-based rhododendronin molecular gyroscope from Example 1. Figure 7 The photostability test results of the cucurbitacin molecular gyroscope in Example 1 in 99% glycerol solution and purified water are shown. Figure 8 The absorption spectra of the cucurbitacin molecular gyroscope in different solvents are shown in Example 1. Figure 9 The detection limit diagram of the molecular gyroscope for cucurbitacin in Example 1 is shown. Figure 10 The emission spectra of the cucurbitacin molecular gyroscope in different decolorized asphalt slurries are shown in Example 1. Detailed Implementation

[0019] This invention provides a cucurbitacin-based azadirachtin molecular gyroscope having the structure shown in Formula I: Formula I.

[0020] This invention provides a method for preparing the above-mentioned cuminyl rhodopsin molecular gyroscope, comprising the following steps: A solution of calciferaldehyde, an organic base solution, and azadirachtin solution were mixed and subjected to a dehydration coupling reaction to obtain a calciferaldehyde-based azadirachtin molecular gyroscope.

[0021] In this invention, unless otherwise specified, all raw materials required for preparation are commercially available products well known to those skilled in the art.

[0022] In this invention, cucurbital is preferably weighed and added to a first solvent for a first mixing to prepare a cucurbital solution. The cucurbital-based rhododendronin molecular gyroscope DHBIC prepared by this invention uses natural and renewable cucurbital and rhododendronin as core functional units, and achieves functional modification of natural molecules through directional coupling and conjugated reconstruction. These natural raw materials are widely available, have good biocompatibility, and are highly compatible with decolorized asphalt slurry composite matrices. They do not introduce harmful impurities during application and can effectively avoid secondary pollution to the slurry system, which is in line with the green development concept of building materials. At the same time, a one-step synthesis route is adopted, which has a simple reaction process, convenient separation and purification, and high synthesis efficiency, greatly simplifying the preparation process and reducing energy consumption and emissions.

[0023] In this invention, the cuminaldehyde is preferably 4-isopropylbenzaldehyde; the first solvent is preferably one or more of ethanol, methanol, dimethyl sulfoxide, acetonitrile, acetone and N,N-dimethylformamide, and is more preferably ethanol.

[0024] In this invention, the first mixing preferably includes two processes: dissolution and stirring performed sequentially. The dissolution temperature is preferably 25°C, and dissolution is mainly carried out by mechanical stirring. The stirring rate during dissolution is preferably 1000~2000 rpm, more preferably 1500 rpm, and the time is preferably 0.3~1.2 h, more preferably 0.75 h. After dissolution, the mixture is placed on a circular shaker and kept in a stirring state. The stirring temperature is preferably 25°C, the stirring speed is preferably 50~300 rpm, more preferably 175 rpm, and the time is preferably 0.5~2.0 h, more preferably 1.25 h.

[0025] In this invention, the concentration of the cuminaldehyde solution is preferably 1-5 mol / L, and more preferably 3 mol / L.

[0026] In this invention, an organic base is weighed, added to a second solvent, and mixed a second time. After mixing, the container is sealed with plastic wrap to prepare an organic base solution.

[0027] In this invention, the organic base preferably includes one or more of trimethylamine, N,N-diisopropylethylamine, pyridine, 4-diethylaminopyridine, imidazole, 4-dimethylaminopyridine, N,N,N',N'-tetramethylethylenediamine, and triethylamine, more preferably triethylamine; the second solvent is preferably a mixed solution of an alcohol solvent and an organic solvent, wherein the volume ratio of the alcohol solvent to the organic solvent is preferably 1 to 5:1, more preferably 3:1; the alcohol solvent preferably includes methanol or ethanol, more preferably ethanol; the organic solvent includes one or more of acetone, acetonitrile, tetrahydrofuran, N,N-dimethylformamide, dimethyl sulfoxide, and ethyl acetate, more preferably acetone.

[0028] In this invention, the second mixing is preferably carried out by direct mixing, the temperature of the second mixing is preferably 10~20℃, more preferably 15℃, the stirring rate is preferably 600~1600 rpm, more preferably 1500 rpm, and the time is preferably 0.1~1.0 h, more preferably 0.55 h.

[0029] In this invention, the concentration of the organic base solution is preferably 1 to 8 mol / L, and more preferably 4 mol / L.

[0030] In this invention, rhododendron extract is preferably weighed, added to a third solvent, and mixed in a third manner to prepare a rhododendron extract solution.

[0031] In this invention, the rhododendronin is preferably 5,7-dihydroxy-2-(4-hydroxyphenyl)-6,8-dimethyl-2,3-dihydrobenzopyran-4-one; the third solvent preferably includes one or more of ethanol, methanol, ethylene glycol, 1,2-propanediol and 1,3-propanediol, and is more preferably ethanol.

[0032] In this invention, the third mixing is carried out by direct mixing, accompanied by continuous nitrogen blowing: the temperature of the third mixing is preferably 30~50℃, more preferably 40℃, the stirring rate is preferably 500~1200 rpm, more preferably 850 rpm, the time is preferably 0.6~1.5 h, more preferably 1.05 h, and the nitrogen blowing rate is preferably 1~3 L / min, more preferably 2 L / min.

[0033] In this invention, the concentration of the rhododendron extract solution is preferably 1-3 mol / L, and more preferably 1 mol / L.

[0034] In this invention, after the azadirachtin solution is mixed and clarified, the cuminaldehyde solution is added dropwise to the azadirachtin solution until the addition is complete. After the addition is complete, the original stirring and nitrogen blowing conditions are maintained for 0.1 to 0.5 h to obtain a premixed solution. Then, the above organic base solution is added to the premixed solution by spraying. After the spraying is completed, the mixture is stirred continuously for 0.1 to 0.3 h. The temperature and nitrogen blowing rate are adjusted to carry out a dehydration coupling reaction to obtain a cuminaldehyde-based azadirachtin molecular gyroscope.

[0035] In this invention, the molar ratio of the cuminaldehyde, the rhododendronin and the organic base is preferably 1~5:1:1~8, and more preferably 2:1:8.

[0036] In this invention, the rate of drop-by-drop addition is preferably controlled to be 1 to 3 drops / s, and more preferably 2 drops / s.

[0037] In this invention, the original stirring and nitrogen blowing conditions are specifically as follows: the stirring rate is preferably 500~1200 rpm, more preferably 850 rpm; the nitrogen blowing rate is preferably 1~3 L / min, more preferably 2 L / min.

[0038] In this invention, the spray rate is preferably 5 mL / min to 15 mL / min, more preferably 10 mL / min, and the stirring rate during the spraying process is preferably increased to 1500 to 2500 rpm, more preferably 2000 rpm.

[0039] In this invention, the temperature of the dehydration coupling reaction is preferably 80~120℃, more preferably 100℃, the stirring rate is preferably 1500~2500 rpm, more preferably 2000 rpm, the time is preferably 2~6 h, more preferably 4 h, and the nitrogen blowing rate is preferably 3~6 L / min, more preferably 4.5 L / min.

[0040] After the dehydration coupling reaction is completed, the present invention preferably performs distillation extraction, purification and cold precipitation, and nitrogen blowing drying on the crude reaction solution to obtain the cuminyl rhododendron molecular gyroscope.

[0041] In this invention, the specific operation of the distillation extraction preferably includes the following steps: transferring the crude reaction solution obtained from the above dehydration coupling reaction to a rotary evaporator for vacuum distillation to remove the solvent from the system; after the first vacuum distillation, adding a mixed solution of ethanol and tetrahydrofuran to redisperse the product, and performing vacuum distillation again, repeating 1 to 3 times; then placing the vacuum distillation product in a mixed system of ethyl acetate and purified water, thoroughly shaking and mixing, allowing it to stand and separate into layers, collecting the organic phase and performing vacuum distillation, and repeatedly extracting 1 to 4 times to enrich the target product; the pressure of the vacuum distillation is preferably -0.09 MPa to -0.07 MPa, the rotation speed is preferably 100 to 300 rpm, and the distillation temperature is preferably 30 to 50°C; the volume ratio of ethanol to tetrahydrofuran is preferably 1 to 5:1.

[0042] In this invention, the specific operation of the purification and cold precipitation preferably includes the following steps: purifying the crude product obtained from the above distillation extraction using a chromatographic solvent via plate chromatography, collecting the eluent corresponding to the target component, diluting it with ethanol, then concentrating it under reduced pressure by distillation, dispersing it by adding a mixed solution of ethanol and purified water, adjusting the solid content of the system to 2-10 mg / mL, and then performing cold precipitation; the chromatographic solvent is preferably a mixed solution of methanol and dichloromethane, and the volume ratio of methanol to dichloromethane is preferably 1:1-10; the volume ratio of dilution is preferably 1-3:1; the pressure of the reduced pressure distillation concentration is preferably -0.09 MPa to -0.07 MPa, the rotation speed is controlled at 100-400 rpm, and the distillation temperature is 30-60℃; the volume ratio of ethanol to purified water is preferably 1:1-6; the temperature of the cold precipitation is preferably 1-10℃, and the time is preferably 12-24 h.

[0043] In this invention, the specific operation of nitrogen blowing drying preferably includes the following steps: dispersing the above-mentioned purified and precipitated solid product in purified water, adjusting the solid content to 1~5 mg / mL, transferring it to a multi-tube vortex mixer, and continuously blowing nitrogen until the solvent is completely removed. Then, the product is placed in a freeze dryer for freeze drying. After drying, a high-purity cucurbitacin molecular gyroscope is obtained, denoted as DHBIC. The nitrogen blowing temperature is preferably 30~50℃, and the nitrogen flow rate is preferably 3~8L / min. The freeze drying temperature is preferably -30℃~-10℃, and the time is preferably 3~8 h.

[0044] This invention provides the application of the above-mentioned cumin-based rhododendron molecular gyroscope or the cumin-based rhododendron molecular gyroscope prepared by the above preparation method in decolorized asphalt slurry. The application method includes the following steps: mixing the cumin-based rhododendron molecular gyroscope with an organic solvent, mixing the resulting cumin-based rhododendron molecular gyroscope solution with decolorized asphalt slurry, measuring the light signal intensity, and obtaining the viscosity of the decolorized asphalt slurry based on the correspondence between light signal intensity and viscosity.

[0045] In this invention, the organic solvent preferably includes ethanol, toluene, cyclohexane, N-methylpyrrolidone or ethyl acetate, and more preferably ethanol.

[0046] In this invention, the concentration of the cucurbitacin molecular gyroscope solution is preferably 10~100 μmol / L; in actual detection, DHBIC only requires milligram-level dosage for accurate sensing and analysis, which is low in cost and suitable for large-scale production and batch quality control testing needs.

[0047] In this invention, the excitation wavelength for measuring the optical signal intensity is preferably 300~500 nm.

[0048] This invention relates to a molecular gyroscope based on cuminaldehyde and azadirachtin, prepared by the directional coupling of cuminaldehyde and azadirachtin, providing a molecular-level tool for precise monitoring of the viscosity of micro-regions in decolorized asphalt slurry. Firstly, this molecular gyroscope forms a π-conjugated system with the directional coupling of cuminaldehyde and azadirachtin as its core. The polycyclic aromatic ring skeleton of azadirachtin acts as a "stator" providing stable support, while the cuminaldehyde-derived side chains containing flexible connecting units act as a "rotor." Relying on the electron delocalization effect, it possesses dynamic rotatability, achieving a synergy between the conjugated structure and rotatable characteristics, ensuring the integrity of the molecular structure and endowing it with sensitivity to micro-environmental changes. Secondly, the rotational freedom of the "rotor" responds to changes in the viscosity of micro-regions in the decolorized asphalt slurry, thereby regulating the electronic transition efficiency of the π-conjugated network, causing a regular shift in the molecular luminescence intensity and emission wavelength, achieving visualized monitoring of micro-region viscosity changes and capturing the viscosity heterogeneity of micro-regions. Third, the polycyclic aromatic ring skeleton structure of rhododendron is stable, avoiding molecular degradation and ensuring the stability and continuity of the light signal; the phenolic hydroxyl functional groups in the molecular structure are stable in an acidic atmosphere, do not affect the acid-base balance of the system, are not affected by impurities, and ensure accurate and reliable monitoring signals.

[0049] For details on the specific sensing and color-generating mechanism of the calcinyl argentin molecular gyroscope in decolorized asphalt slurry, please refer to [link to relevant documentation]. Figure 1DHBIC, with its unique stator-rotor configuration and π-conjugated framework, constructs a controllable molecular chromogenic and viscosity response mechanism, which can be used as an optical signal switch to achieve real-time, dynamic, and visual monitoring of the viscosity of micro-regions in decolorized asphalt slurry. Addressing the issue of micro-region viscosity heterogeneity caused by the uneven distribution of thickening components such as tar colloids and lignin pyrolysis fragments within the system, DHBIC senses changes in fluid micro-resistance through the dynamic rotational degrees of freedom of the molecular rotor, converting differences in the mechanical environment into a quantifiable fluorescence signal, thus achieving precise quantitative characterization of micro-region viscosity. From the perspective of the chromogenic mechanism, this molecular gyroscope possesses specific photoresponse characteristics adapted to the decolorized asphalt slurry matrix, generating stable characteristic fluorescence emission under optimized excitation conditions. With its large Stokes shift and excellent spectral anti-interference capability, it avoids background fluorescence and scattering interference, ensuring the stability and recognizability of the optical signal output, achieving highly sensitive and accurate viscosity sensing and detection. Meanwhile, the fluorescence emission intensity of DHBIC is positively correlated with the consistency of the decolorized asphalt slurry. Its weak light signal intensity is suitable for low-viscosity decolorized asphalt slurry applications, while its strong light signal intensity can distinguish viscosity gradients of different grades of slurry, meeting the needs of medium- and high-viscosity engineering applications. Furthermore, DHBIC possesses excellent chemical stability and environmental resistance. The rigid framework of the azadirachtin polycyclic aromatic rings ensures its stable coexistence in the composite polar system, and the phenolic hydroxyl functional groups are stable in a weakly acidic environment, without side reactions or disruption of the system's acid-base balance, thus guaranteeing accurate and reliable long-term detection signals from a structural perspective.

[0050] The technical solutions provided by the present invention will be described in detail below with reference to the embodiments, but they should not be construed as limiting the scope of protection of the present invention.

[0051] Example 1

[0052] 300.3 g of cuminaldehyde was added to ethanol and stirred at 1500 rpm for 0.75 h at 25 °C. After the cuminaldehyde was dissolved and mixed evenly, the system was transferred to a circular shaker and stirred at 175 rpm for 1.25 h to obtain a cuminaldehyde solution with a concentration of 3 mol / L. 300.31 g of rhododendron extract was added to ethanol and stirred at 850 rpm for 1.05 h at 40 °C, with nitrogen blowing during the process at a rate of 2 L / min, to obtain a rhododendron extract solution with a concentration of 1 mol / L. Add a mixture of ethanol and acetone in a volume ratio of 3:1 to a container containing 404.8 g of triethylamine. Stir at 1500 rpm for 0.55 h at 15 °C. After mixing, seal the container with plastic wrap to obtain a triethylamine organic base solution with a concentration of 4 mol / L. After the rhododendron solution became clear, cuminaldehyde solution was added to the rhododendron solution at a rate of 2 drops / s. The mixture was stirred at 850 rpm for 0.3 h at 40 °C, accompanied by nitrogen blowing at a rate of 2 L / min, to obtain a premix. Triethylamine organic base solution was added to the premix via spray at a rate of 10 mL / min. During the spraying process, the stirring rate was increased to 2000 rpm, and stirring was continued for 0.2 h after the spraying was completed. The mixture was then stirred at 2000 rpm for 4.0 h at 100 °C, accompanied by nitrogen blowing at a rate of 4.5 L / min, until the directional coupling reaction between cuminaldehyde and rhododendron was completed. After the reaction was completed, the crude reaction solution was sequentially subjected to distillation extraction, purification and cold precipitation, and nitrogen blowing drying to obtain a high-purity product. (1) Distillation extraction: The crude reaction solution was transferred to a rotary evaporator and the pressure of vacuum distillation was controlled at -0.08 MPa, the rotation speed at 200 rpm and the distillation temperature at 40℃. After the first distillation, a mixed solution of ethanol and tetrahydrofuran in a volume ratio of 3:1 was added to redisperse the product. The product was then distilled again under vacuum under the same conditions. This operation was repeated twice. The distilled product was then placed in a mixed system of ethyl acetate and purified water in a volume ratio of 2:1. After thorough shaking and mixing, the mixture was allowed to stand and separate into layers. The organic phase was collected and the solvent was removed by vacuum distillation under the conditions described above. The extraction was repeated twice to enrich the target product. (2) Purification and cold precipitation: The crude product obtained by distillation extraction was purified by plate chromatography. The chromatographic solution was a mixture of methanol and dichloromethane in a volume ratio of 1:5. The eluent corresponding to the target component was collected and diluted with ethanol in a volume ratio of 2:1. The solution was concentrated by vacuum distillation at -0.08 MPa, with the rotation speed controlled at 300 rpm and the distillation temperature at 50℃. After concentration, a mixture of ethanol and purified water in a volume ratio of 1:3 was added for dispersion. The solid content of the system was adjusted to 6 mg / mL. The system was placed in a cold precipitation environment at 5℃ for 18 h to precipitate solid product. (3) Nitrogen blowing drying: The solid product obtained by cold precipitation was dispersed in purified water, the solid content was adjusted to 3 mg / mL, and transferred to a multi-tube vortex mixer. The temperature was set at 40℃ and the nitrogen flow rate was 5.5 L / min. Nitrogen blowing was continued until the solvent was completely removed. Then the product was placed in a freeze dryer and the drying temperature was controlled at -20℃ and the drying time was 5.5 h. After drying, a high-purity cucurbitacin molecular gyroscope was obtained, denoted as DHBIC.

[0053] The DHBIC prepared in this embodiment was weighed, and the yield of DHBIC in this embodiment was 520.32 g. The yield was calculated, and the yield of DHBIC in this embodiment was 92.8%.

[0054] The relative molecular mass and chemical structure of the DHBIC prepared in this embodiment were analyzed, and the high-resolution mass spectrum and nuclear magnetic resonance spectrum of the DHBIC in this embodiment were obtained, as shown in the figures below. Figures 2-3 ;Depend on Figure 2 It is known that the relative molecular mass of the tanshinone-conjugated chromophore DHBIC is 560.69200 [M]. + The molecular formula of formula I is C 37 H 36 O5, with a theoretical relative mass estimate of 560.69000, shows that the product obtained in Example 1 is consistent with the target product in terms of relative molecular mass; from Figure 3 From this, we can know that 13 C NMR (101 MHz, DMSO-d6) δ 197.85, 164.71, 164.13, 162.22, 158.52, 148.51, 134.25, 133.11, 130.12, 129.53, 128.28, 127.48, 126.45, 117.04, 104.28, 103.55, 99.02, 84.05, 43.75, 37.15, 24.98. The carbon skeleton shift in its molecular structure was confirmed, and it can be identified as the target product, cucurbital-based rhododendronin molecular gyroscope DHBIC.

[0055] Example 2

[0056] 148.2 g of cuminaldehyde was added to ethanol and stirred at 1000 rpm for 1.2 h at 25 °C. After the cuminaldehyde was dissolved and mixed evenly, the system was transferred to a circular shaker and stirred at 300 rpm for 0.5 h to obtain a cuminaldehyde solution with a concentration of 1 mol / L. 300.31 g of rhododendron extract was added to ethanol and stirred at 500 rpm for 1.5 h at 30 °C, with nitrogen blowing at a rate of 1 L / min, to obtain a rhododendron extract solution with a concentration of 1 mol / L. Add a mixture of ethanol and acetone in a volume ratio of 1:1 to a container containing 101.20 g of triethylamine. Stir at 600 rpm for 1.0 h at 10 °C. After mixing, seal the container with plastic wrap to obtain a triethylamine organic base solution with a concentration of 1 mol / L. After the rhododendron solution was clarified, the cumin solution was added to the rhododendron solution at a rate of 1 drop / s, and stirred at 500 rpm for 0.5 h at 30℃, accompanied by nitrogen blowing at a rate of 1 L / min, to obtain the premixed solution. The triethylamine organic base solution was added to the premixed solution by spraying at a rate of 5 mL / min. During the spraying process, the stirring rate was increased to 1500 rpm. After the spraying was completed, the stirring was continued for 0.3 h. The mixture was stirred at 1500 rpm at 80℃ for 6.0 h, accompanied by nitrogen blowing at a rate of 3 L / min, until the directional coupling reaction of cuminaldehyde and azadirachtin was completed. After the reaction was completed, the crude reaction solution was sequentially subjected to distillation extraction, purification and cold precipitation, and nitrogen blowing drying to obtain a high-purity product. (1) Distillation extraction: The crude reaction solution was transferred to a rotary evaporator and the pressure of vacuum distillation was controlled at -0.07 MPa, the rotation speed at 100 rpm and the distillation temperature at 30℃. After the first distillation, a mixed solution of ethanol and tetrahydrofuran in a volume ratio of 1:1 was added to redisperse the product. The product was then distilled again under vacuum under the same conditions. This operation was repeated once. The distilled product was then placed in a mixed system of ethyl acetate and purified water in a volume ratio of 1:1. After thorough shaking and mixing, the mixture was allowed to stand and separate into layers. The organic phase was collected and the solvent was removed by vacuum distillation under the conditions described above. The extraction was repeated once to enrich the target product. (2) Purification and cold precipitation: The crude product obtained by distillation extraction was purified by plate chromatography. The chromatographic solution was a mixture of methanol and dichloromethane in a volume ratio of 1:10. The eluent corresponding to the target component was collected and diluted with ethanol in a volume ratio of 1:1. The solution was concentrated by vacuum distillation at -0.09 MPa, with the rotation speed controlled at 100 rpm and the distillation temperature at 60℃. After concentration, a mixture of ethanol and purified water in a volume ratio of 1:1 was added for dispersion. The solid content of the system was adjusted to 2 mg / mL. The system was placed at 1℃ for cold precipitation for 12 h to precipitate the solid product. (3) Nitrogen blowing drying: The solid product obtained by cold precipitation was dispersed in purified water, the solid content was adjusted to 1 mg / mL, and transferred to a multi-tube vortex mixer. The temperature was set to 30℃ and the nitrogen flow rate was 3 L / min. Nitrogen blowing was continued until the solvent was completely removed. Then the product was placed in a freeze dryer and the drying temperature was controlled at -30℃ and the drying time was 3 h. After drying, a high-purity cucurbitacin molecular gyroscope was obtained, denoted as DHBIC.

[0057] The DHBIC prepared in this embodiment was weighed, and the yield of DHBIC in this embodiment was 505.18 g. The yield was calculated, and the yield of DHBIC in this embodiment was 90.1%.

[0058] The relative molecular mass and chemical structure of the DHBIC prepared in this embodiment were analyzed. The relative molecular mass of the DHBIC in this embodiment was also 560.69200, and its nuclear magnetic resonance spectrum was consistent with that of Example 1.

[0059] Example 3

[0060] 741.0 g of cuminaldehyde was added to ethanol and stirred at 2000 rpm for 0.3 h at 25 °C. After the cuminaldehyde was dissolved and mixed evenly, the system was transferred to a circular shaker and stirred at 300 rpm for 0.5 h to obtain a cuminaldehyde solution with a concentration of 5 mol / L. 300.31 g of rhododendron extract was added to ethanol and stirred at 1200 rpm for 0.6 h at 50 °C, with nitrogen blowing at a rate of 3 L / min, to obtain a rhododendron extract solution with a concentration of 3 mol / L. Add a mixture of ethanol and acetone in a volume ratio of 5:1 to a container containing 809.52 g of triethylamine. Stir at 1600 rpm for 0.1 h at 20 °C. After mixing, seal the container with plastic wrap to obtain a triethylamine organic base solution with a concentration of 8 mol / L. After the rhododendron solution became clear, cuminaldehyde solution was added to the rhododendron solution at a rate of 3 drops / s. The mixture was stirred at 1200 rpm for 0.1 h at 50 °C, accompanied by nitrogen blowing at a rate of 3 L / min, to obtain a premix. Triethylamine organic base solution was added to the premix via spray at a rate of 15 mL / min. During the spraying process, the stirring rate was increased to 2500 rpm, and stirring was continued for 0.1 h after the spraying was completed. The mixture was then stirred at 2500 rpm for 2.0 h at 120 °C, accompanied by nitrogen blowing at a rate of 6 L / min, until the directional coupling reaction between cuminaldehyde and rhododendron was completed. After the reaction was completed, the crude reaction solution was sequentially subjected to distillation extraction, purification and cold precipitation, and nitrogen blowing drying to obtain a high-purity product. (1) Distillation extraction: The crude reaction solution was transferred to a rotary evaporator and the pressure was controlled at -0.07 MPa, the rotation speed at 300 rpm and the distillation temperature at 50℃. After the first distillation, a mixed solution of ethanol and tetrahydrofuran in a volume ratio of 5:1 was added to redisperse the product. The product was then distilled again under the same conditions. This operation was repeated 3 times. The distilled product was then placed in a mixed system of ethyl acetate and purified water in a volume ratio of 3:1. After thorough shaking and mixing, the mixture was allowed to stand and separate into layers. The organic phase was collected and the solvent was removed by vacuum distillation under the same conditions. The extraction was repeated 4 times to enrich the target product. (2) Purification and cold precipitation: The crude product obtained by distillation extraction was purified by plate chromatography. The chromatographic solution was a mixture of methanol and dichloromethane in a volume ratio of 1:1. The eluent corresponding to the target component was collected and diluted with ethanol in a volume ratio of 3:1. The eluent was concentrated by vacuum distillation at -0.07 MPa, with the rotation speed controlled at 400 rpm and the distillation temperature at 30℃. After concentration, a mixture of ethanol and purified water in a volume ratio of 1:6 was added for dispersion. The solid content of the system was adjusted to 10 mg / mL. The system was placed at 10℃ for cold precipitation for 24 h to precipitate solid product. (3) Nitrogen blowing drying: The solid product obtained by cold precipitation was dispersed in purified water, the solid content was adjusted to 5 mg / mL, and transferred to a multi-tube vortex mixer. The temperature was set to 50℃ and the nitrogen flow rate was 5 L / min. Nitrogen blowing was continued until the solvent was completely removed. Then the product was placed in a freeze dryer, and the drying temperature was controlled at -10℃ and the drying time was 3 h. After drying, a high-purity cucurbitacin molecular gyroscope was obtained, denoted as DHBIC.

[0061] The DHBIC prepared in this embodiment was weighed, and the yield of DHBIC in this embodiment was 511.91 g. The yield was calculated, and the yield of DHBIC in this embodiment was 91.3%.

[0062] The relative molecular mass and chemical structure of the DHBIC prepared in this embodiment were analyzed. The relative molecular mass of the DHBIC in this embodiment was also 560.69200, and its nuclear magnetic resonance spectrum was consistent with that of Example 1.

[0063] Performance testing

[0064] 1. The DHBIC prepared in Example 1 was subjected to viscosity sensitivity testing, Stokes displacement testing, light stability testing, polarity tolerance testing, and detection limit testing: (1) Viscosity sensitivity test: ① Qualitative analysis: By adjusting the proportions of glycerol and water (the volume fractions of glycerol in the glycerol solutions were 0%, 10%, 30%, 50%, 70%, and 99%, and their viscosity values ​​are shown in Table 1), glycerol solutions ranging from 1.0 to 956.0 cP were obtained. DHBIC was added to each solution, and the concentration of DHBIC in the solutions was adjusted to 10 μmol / L. Fluorescence spectroscopy was performed at room temperature using a characteristic excitation wavelength of 420 nm. The spectral response results are shown in Table 1. Figure 4 ; Table 1. Correspondence between glycerol solutions of different volume fractions and viscosity values

[0065] Depend on Figure 4It is evident that DHBIC exhibits extremely high sensitivity to changes in system viscosity: as the simulated system viscosity increases from 1.0 cP to 956.0 cP, the fluorescence emission peak intensity of DHBIC shows a significant gradient enhancement trend with increasing viscosity. The fluorescence signal is weak in the low-viscosity system, while the fluorescence intensity increases significantly in the high-viscosity system, and the emission peak position (543 nm) shows no significant shift, indicating a stable signal response. This characteristic can intuitively distinguish the signal differences of different viscosity grades of decolorized asphalt slurry, clearly corresponding to the performance differences from low-viscosity sprayable, medium-viscosity general-purpose to high-viscosity adhesive products, providing direct support for rapid and visual screening of decolorized asphalt slurry of different specifications.

[0066] ② Quantitative analysis: To quantify the monitoring effectiveness of DHBIC on the micro-region viscosity of decolorized asphalt slurry, the logarithms of fluorescence intensity and viscosity values ​​within the range of 1.0–956.0 cP were used for linear fitting (see Table 2). The results are shown in [Table 2]. Figure 5 ; Table 2. Logarithmic function values ​​of fluorescence intensity and viscosity of DHBIC obtained in Example 1

[0067] like Figure 5 As shown, the fitting results strictly follow the Förster-Hoffmann relation, log(I 543 The linear correlation coefficient R between ) and log(η) 2 With a viscosity sensitivity coefficient (slope) of 0.55, the two have an excellent linear correlation, enabling precise quantitative characterization of viscosity changes in decolorized asphalt slurry. It can capture the subtle viscosity fluctuations in micro-regions caused by uneven distribution of thickening components in the system, breaking through the limitation of traditional macroviscometers in detecting micro-region heterogeneity.

[0068] Therefore, DHBIC possesses the core advantages of high viscosity sensitivity, good linear response, excellent visualization, wide measurement range, and in-situ undisturbed operation. Furthermore, it does not damage the microstructure and component integrity of the decolorized asphalt slurry. It can capture the micro-region viscosity changes of decolorized asphalt slurry with different refining levels and different batches in real time in situ. The viscosity of the system can be intuitively determined by the intensity of the fluorescence signal. It can achieve precise control of thickening components, rapid identification of product grades, and optimization of batch stability during the decolorized asphalt slurry processing. It shows broad application prospects and great engineering value in the quality control, scenario adaptation, and high-value upgrading of commercially available decolorized asphalt slurry.

[0069] (2) Stokes shift test: DHBIC was prepared into a 10 μmol / L ethanol solution, and its UV-Vis absorption spectrum and fluorescence emission spectrum were measured at room temperature. The Stokes shift was calculated, and the results are shown in the figure. Figure 6 ; Depend on Figure 6 It is known that DHBIC exhibits a Stokes shift of 117.7 nm. This large Stokes shift effectively reduces the spectral overlap between the excitation and emission wavelengths, significantly reducing background interference from excitation and scattered light on the emission signal and substantially improving the signal-to-noise ratio. Simultaneously, this characteristic avoids the influence of scattered light from light-colored resins, emulsifiers, and additives in the decolorized asphalt slurry system, as well as the background fluorescence of the solvent. This overcomes background interference, prevents signal distortion, and ensures high contrast and accuracy of the detection signal, achieving in-situ, high-contrast, and high-signal-noise ratio light signal release, thus achieving excellent visualization and characterization effects. This characteristic makes it highly promising for micro-area viscosity monitoring of decolorized asphalt slurry. It can effectively overcome background interference in complex slurry systems, achieving in-situ, high-contrast, and high-signal-noise ratio light signal release, ensuring the stability and accuracy of detection results. It provides crucial spectroscopic support for formula optimization, process control, and batch quality control of decolorized asphalt slurry in colored pavement paving, bridge deck waterproofing bonding layer construction, and old road maintenance, demonstrating significant application value.

[0070] (3) Photostability test: 3.36 mg of DHBIC was weighed and dissolved in ethanol to prepare a stock solution with a concentration of 6 mmol / L. This stock solution was then added to purified water (low viscosity, simulating a refined decolorized asphalt slurry base system) and a 99% glycerol solution (high viscosity, simulating a concentrated decolorized asphalt slurry finished product system), respectively, with the concentration of DHBIC in both solutions adjusted to 10 μmol / L. The system was continuously irradiated with a characteristic excitation wavelength of 420 nm, and the change in fluorescence signal intensity within 60 min was monitored to verify the photostability of DHBIC in low-viscosity and high-viscosity decolorized asphalt slurry scenarios. The test results are shown in […]. Figure 7 ; Depend on Figure 7It is evident that DHBIC exhibits excellent photostability in both extreme viscosity simulated decolorized asphalt slurry systems: under 60 minutes of continuous excitation irradiation, the fluorescence signal intensity showed no significant attenuation in either the low-viscosity refined decolorized asphalt slurry simulation system or the high-viscosity concentrated simulation system. The signal in the low-viscosity system remained at a low response level, while the signal in the high-viscosity system remained stably at a high response level, unaffected by both viscosity differences and long-term light exposure. This characteristic is of core value for the application of DHBIC in micro-area viscosity monitoring of decolorized asphalt slurry: during outdoor colored pavement construction, bridge deck waterproofing bonding layer curing, and long-term storage, decolorized asphalt slurry is easily exposed to long-term natural light. Traditional fluorescent probes are prone to signal distortion due to photobleaching, failing to provide reliable data for construction process monitoring and subsequent performance evaluation. High photostability ensures continuous and accurate capture of micro-area viscosity changes during long-term monitoring throughout the entire lifecycle of decolorized asphalt slurry, providing solid data support for the regulation of its thickening components and the stable quality control of different batches. It also meets the monitoring needs of all scenarios, from low-viscosity sprayable products to high-viscosity adhesive products, significantly enhancing its competitiveness and promotion potential in the field of refined quality control and engineering applications of decolorized asphalt slurry.

[0071] (4) Polarity tolerance test: 2.80 mg of DHBIC was weighed and dissolved in ethanol to prepare a stock solution with a concentration of 5 mmol / L. This stock solution was added to ethanol, dimethyl sulfoxide, N,N-dimethylformamide, tetrahydrofuran, dichloromethane, methanol, acetonitrile, and ethyl acetate, respectively, and the concentration of DHBIC in the solution was adjusted to 10 μmol / L. The solution was continuously irradiated at room temperature with a characteristic excitation wavelength of 420 nm to investigate the effect of solvent polarity change on its optical signal absorption performance, simulating the interference of the complex polar environment of decolorized asphalt slurry on DHBIC. The results are shown in […]. Figure 8 ; Depend on Figure 8It is evident that DHBIC exhibits highly consistent absorption spectra in solvent systems of varying polarities: the absorption peak is concentrated around 420 nm, and the peak shape, peak position, and absorbance intensity show no significant shifts or fluctuations in different solvents, demonstrating excellent solvent polarity tolerance and insensitivity to changes in solution polarity. This characteristic is crucial for the application of DHBIC in micro-area viscosity monitoring of decolorized asphalt slurry: decolorized asphalt slurry is a multi-component composite system, and its polarity can fluctuate significantly due to the degree of refining, the addition of processing aids, and batch differences. Furthermore, subtle changes in the proportion of polar components within the system can easily trigger overall polarity shifts. If molecular monitoring tools are sensitive to polarity, polarity fluctuations can easily lead to optical signal distortion, failing to accurately reflect the actual micro-area viscosity of the decolorized asphalt slurry, thus affecting the control of thickening components and product quality management. This characteristic ensures that the DHBIC optical signal only responds to changes in micro-area viscosity, unaffected by fluctuations in the polar components of the system, thereby achieving accurate and interference-free viscosity monitoring. This characteristic provides universal support for viscosity monitoring of decolorized asphalt slurry at different processing stages and in different batches. It can be adapted to the quality control needs of the entire process from the initial refining stage to the finished product stage, and shows excellent application adaptability and promotion potential in the quality control of decolorized asphalt slurry in multiple scenarios such as colored pavement paving, bridge deck waterproofing, and landscape walkway maintenance.

[0072] (5) Detection limit test: Weigh 2.24 mg DHBIC, dissolve it in ethanol to prepare a stock solution with a concentration of 4 mmol / L, dilute the stock solution to 10 μmol / L, and then add it to water-glycerol mixed solutions of different proportions to simulate the substrate system with extremely low viscosity gradually increasing in the early stage of decolorized asphalt slurry refining (from coarse filtration to preliminary purification stage). Under room temperature conditions, continuously irradiate with a characteristic excitation wavelength of 420 nm to test its viscosity detection sensitivity, and obtain the viscosity-optical signal linear fitting graph of DHBIC. The results are shown in […]. Figure 9 ; Depend on Figure 9 It can be seen that within the extremely low viscosity range corresponding to the initial stage of refining decolorized asphalt slurry, the viscosity value of DHBIC exhibits an excellent linear relationship with the logarithm of light signal emission intensity, and the coefficient of determination R0 is well-fitted. 2The correlation between the two is as high as 0.98, and the calculated lower limit of detection is 1.016 cP, indicating a very high degree of correlation and reliable test data. This linear relationship directly proves that DHBIC can accurately respond to subtle fluctuations in viscosity in the low-micro range through changes in light signal intensity, demonstrating its ultra-sensitive ability to viscosity changes and a low lower limit of detection. This low lower limit of detection characteristic is of irreplaceable importance for the monitoring and refining control of decolorized asphalt slurry: In the early stage of refining decolorized asphalt slurry (when impurities are not completely removed and the content of thickening components is extremely low), the viscosity of the system is generally at an extremely low level. Traditional macroviscometers are limited by their detection accuracy and find it difficult to capture subtle viscosity fluctuations in this range, which can easily lead to inaccurate control of the degree of refining—over-refining will consume effective binder components, while insufficient refining will result in too many residual impurities, affecting product stability and durability. DHBIC's low detection limit can accurately cover the entire range of decolorized asphalt slurry monitoring from low viscosity in the early stage of refining to medium and high viscosity. In particular, it can effectively capture micro-viscosity disturbances that are difficult to identify by traditional tools, providing molecular-level data support for dynamic adjustment of refining process parameters and precise control of the accumulation of thickening components. This ensures that the quality of decolorized asphalt slurry is within a controllable range from the initial stage, demonstrating great application potential and engineering value in the fine processing, batch quality control and scenario adaptation of decolorized asphalt slurry.

[0073] 2. Weigh 1.68 mg of DHBIC prepared in Example 1, dissolve it in ethanol, and prepare a stock solution with a concentration of 3 mmol / L. Then, add this stock solution to three different brands of commercially available decolorized asphalt slurry (Decolorized asphalt slurry 1 was purchased from Shanghai GoGreen GCA-05, Decolorized asphalt slurry 2 was purchased from Jiangsu Longchishan YOU-60, and Decolorized asphalt slurry 3 was purchased from Zhejiang Luxiang LX-800), adjusting the concentration of DHBIC in each solution to 10 μmol / L. The viscosities of the three commercially available decolorized asphalt slurries were 418.0 cP, 631.0 cP, and 809.0 cP, respectively (all within the core range of 300–900 cP for engineering applications), covering mainstream product specifications from low-viscosity spraying to medium-to-high-viscosity adhesive types. Emission spectra were measured at room temperature using a characteristic excitation wavelength of 420 nm as the external light source. The results are shown in [Figure showing the results]. Figure 10 See Table 1.

[0074] Table 1. Optical signal intensity and viscosity values ​​of different decolorized asphalt slurries

[0075] Combination Figure 10As shown in Table 1, the light signal intensity of the cucurbitacin molecular gyroscope exhibits a clear gradient increase with increasing system viscosity: the light signal intensity of low-viscosity decolorized asphalt slurry (418.0 cP) is 1288.2, corresponding to the system's excellent fluidity and suitability for thin-layer spraying of colored pavements; the light signal intensity of medium-viscosity decolorized asphalt slurry (631.0 cP) increases to 1584.9, reflecting the system's balance between fluidity and adhesion, meeting the performance requirements of landscape walkways and bicycle paths; the light signal intensity of high-viscosity decolorized asphalt slurry (809.0 cP) reaches 1819.7, matching the system's high stability and strong adhesion, making it suitable for scenarios with high adhesion requirements, such as bridge deck waterproofing bonding layers and colored maintenance of old pavements. Notably, this molecular gyroscope exhibits excellent response stability and anti-interference capabilities in the complex system of decolorized asphalt slurry. Its light signal intensity can accurately quantify the differences in micro-area fluid resistance of slurries with different viscosity grades. Without relying on large-scale macroscopic viscosity testing equipment, it can achieve rapid qualitative screening and grade differentiation of product consistency through light intensity differences. It is suitable for batch quality control and rapid product grade determination needs in the production site of commercially available decolorized asphalt slurry, providing a convenient and efficient molecular-level detection solution for the industrialized and refined quality control of this type of material. It shows significant application potential and engineering value in the scenario-based application and high-value upgrading of decolorized asphalt slurry.

[0076] As can be seen from the above embodiments, the present invention provides a cucurbitacin-based molecular gyroscope. Its unique "stator-rotor" structure and the π-conjugated system running through the molecule endow it with excellent viscosity response characteristics and optical properties. It can efficiently convert the micro-area viscosity signal of decolorized asphalt slurry into a quantifiable optical signal, realizing rapid, in-situ, and visual detection of the micro-area viscosity of commercially available decolorized asphalt slurry. For decolorized asphalt slurry, a pseudoplastic composite system containing thickening components, DHBIC can achieve in-situ, undisturbed detection without relying on traditional rotational shearing operations, effectively avoiding the damage to the micro-network structure of the slurry caused by macroviscometers. It can truly reflect the in-situ micro-area viscosity state, which is particularly crucial for the consistency control and quality management of refined, conventional, and concentrated decolorized asphalt slurries. Performance tests confirm that DHBIC has outstanding viscosity response performance, exhibiting a stable linear response within a wide viscosity range of 1.0~956.0 cP, log(I 543 The coefficient of determination R between ) and log(η) 2With a viscosity sensitivity coefficient as high as 0.96 and 0.55, it can sensitively capture subtle viscosity fluctuations caused by uneven distribution of thickening components in decolorized asphalt slurry, accurately distinguishing grade differences within the core viscosity range of 300-900 cP for commercially available products. Simultaneously, its low detection limit of 1.0 cP covers the entire processing flow of the slurry, from the initial low-viscosity base to the high-viscosity finished product, providing precise data support for dynamic adjustment of process parameters. In terms of optical and chemical stability, DHBIC exhibits multiple advantages in adapting to the complex system of decolorized asphalt slurry: Firstly, the large Stokes shift of 117.7 nm effectively reduces background interference from excitation and scattered light, significantly improving the signal-to-noise ratio and overcoming the background fluorescence effects of light-colored resins, emulsifiers, and other components in the slurry, ensuring high signal contrast and visualization; secondly, at 60... Under continuous illumination, the fluorescence signal shows no significant attenuation, demonstrating excellent photostability and meeting the long-term monitoring needs during slurry storage and construction curing stages. Thirdly, from a molecular structure perspective, the polycyclic aromatic skeleton of azadirachtin exhibits extremely strong structural stability, enabling it to remain stable in the composite polar solvent system of decolorized asphalt slurry, effectively preventing molecular degradation and ensuring the stability and continuity of the light signal release. Furthermore, the phenolic hydroxyl functional groups contained in the molecular structure are not prone to chemical reactions in the solution atmosphere of decolorized asphalt slurry, allowing it to remain stably without affecting the system's acid-base balance. It will not interact with emulsifiers, tackifying resins, or other components in the slurry, nor will it be interfered with by impurities in the system, ensuring the accuracy and reliability of the monitoring signal. Fourthly, in various polar solvents, the absorption spectrum of DHBIC shows no significant shift, indicating insensitivity to changes in solution polarity. It can stably withstand the composite polar environment of decolorized asphalt slurry, avoiding interference from batch-to-batch polarity fluctuations on the detection signal. In summary, this molecular gyroscope requires no complex sample pretreatment and can be directly adapted to commercially available decolorized asphalt slurries with different refining processes and viscosity specifications. It fills the gap in molecular-level viscosity detection technology for commercially available decolorized asphalt slurries. In actual testing, DHBIC only requires milligram-level dosage for accurate sensing and analysis, resulting in low cost. It is suitable for large-scale production and batch quality control testing needs, providing new ideas for the innovative application of natural product derivatives in the field of asphalt-based functional material testing. It also provides key support for multi-scenario quality control and high-value upgrading of decolorized asphalt slurries, and has broad engineering application prospects and promotion potential.

[0077] The above description is only a preferred embodiment of the present invention. It should be noted that for those skilled in the art, several improvements and modifications can be made without departing from the principle of the present invention, and these improvements and modifications should also be considered within the scope of protection of the present invention.

Claims

1. A calcinyl rhododendron molecular gyroscope, characterized in that, It has the structure shown in Equation I: Equation I.

2. The preparation method of the cuminyl rhododendron molecular gyroscope according to claim 1, characterized in that, Includes the following steps: A solution of calciferaldehyde, an organic base solution, and azadirachtin solution were mixed and subjected to a dehydration coupling reaction to obtain a calciferaldehyde-based azadirachtin molecular gyroscope.

3. The preparation method according to claim 2, characterized in that, The cuminaldehyde in the cuminaldehyde solution is 4-isopropylbenzaldehyde, and the solvent in the cuminaldehyde solution includes one or more of ethanol, methanol, dimethyl sulfoxide, acetonitrile, acetone and N,N-dimethylformamide; The concentration of the calciform solution is 1~5 mol / L.

4. The preparation method according to claim 3, characterized in that, The organic base in the organic base solution includes one or more of trimethylamine, N,N-diisopropylethylamine, pyridine, 4-diethylaminopyridine, imidazole, 4-dimethylaminopyridine, N,N,N',N'-tetramethylethylenediamine, and triethylamine. The solvent in the organic base solution is a mixed solution of an alcohol solvent and an organic solvent in a volume ratio of 1 to 5:

1. The alcohol solvent includes methanol or ethanol, and the organic solvent includes one or more of acetone, acetonitrile, tetrahydrofuran, N,N-dimethylformamide, dimethyl sulfoxide, and ethyl acetate. The concentration of the organic base solution is 1~8 mol / L.

5. The preparation method according to claim 4, characterized in that, The rhododendron extract in the rhododendron extract solution is 5,7-dihydroxy-2-(4-hydroxyphenyl)-6,8-dimethyl-2,3-dihydrobenzopyran-4-one, and the solvent in the rhododendron extract solution includes one or more of ethanol, methanol, ethylene glycol, 1,2-propanediol and 1,3-propanediol. During the preparation of the rhododendron solution, continuous nitrogen blowing is carried out at a rate of 1-3 L / min, the mixing temperature is 30-50℃, the stirring rate is 500-1200 rpm, and the time is 0.6-1.5 h. The concentration of the rhododendron extract solution is 1~3 mol / L.

6. The preparation method according to claim 5, characterized in that, The molar ratio of the cumin, the rhododendronin and the organic base is 1~5:1:1~8.

7. The preparation method according to claim 2, characterized in that, The dehydration coupling reaction was carried out at a temperature of 80-120℃, a stirring rate of 1500-2500 rpm, a nitrogen blowing rate of 3-6 L / min, and a time of 2-6 h.

8. The application of the cumin-based rhododendronin molecular gyroscope according to claim 1 or the cumin-based rhododendronin molecular gyroscope prepared by any one of claims 2 to 7 in decolorizing asphalt slurry, characterized in that, The method of application includes the following steps: mixing a calciferol-based rhododendron molecular gyroscope with an organic solvent, mixing the resulting calciferol-based rhododendron molecular gyroscope solution with decolorized asphalt slurry, measuring the light signal intensity, and obtaining the viscosity of the decolorized asphalt slurry based on the correspondence between light signal intensity and viscosity.

9. The application according to claim 8, characterized in that, The organic solvents include ethanol, toluene, cyclohexane, N-methylpyrrolidone, or ethyl acetate.

10. The application according to claim 8, characterized in that, The concentration of the cucurbitacin molecular gyroscope solution is 10~100 μmol / L; The excitation wavelength for the optical signal intensity measurement is 300~500 nm.

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