CN112625673A - Amphiphilic host-guest fluorescent material capable of rapidly identifying potential fingerprints and preparation method and application thereof - Google Patents
Amphiphilic host-guest fluorescent material capable of rapidly identifying potential fingerprints and preparation method and application thereof Download PDFInfo
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Abstract
The invention relates to the technical field of amphiphilic host-guest fluorescent materials, and provides a preparation method of an amphiphilic host-guest fluorescent material for rapidly identifying potential fingerprints. The hydrophobic hemicyanine fluorescent dye has the characteristic of low toxicity, and can reduce the toxicity harm of the operation of displaying potential fingerprints; the amphiphilic host-guest fluorescent material can be completely dissolved in deionized water, and the prepared aqueous solution is used, so that grease in fingerprints can be quickly combined, the amphiphilic host-guest fluorescent material can be suitable for displaying potential fingerprints on different carriers, and has high selectivity; and the host-guest fluorescent material and the grease can be combined for color development on the premise of not damaging the grease traces in the fingerprints, and the sensitivity is higher.
Description
Technical Field
The invention relates to the technical field of amphiphilic host-guest fluorescent materials, in particular to an amphiphilic host-guest fluorescent material capable of rapidly identifying potential fingerprints and a preparation method and application thereof.
Background
The fingerprint refers to mastoid pattern on the surface of human hand skin, and is typical genetic character. Therefore, fingerprints are the most useful type of physical evidence, are known as the "first evidence" as a physical evidence, and are widely applied to case pursuit and criminal authentication. How to find, display and collect fingerprints on various objects in a crime scene is a key problem of fingerprint utilization.
Currently, a number of approaches have been developed to improve the potential sweat fingerprint. The traditional powder spraying method, starting at the end of the 19 th century, is a very old method for identifying potential fingerprints. In the powder spray method, powder particles are mechanically or physically attached to the aqueous or oily components in the latent fingerprint residue, thereby achieving the purpose of fingerprint identification. The powder in the powder spray process is often composed of resin powder, metal powder and fluorescent powder, and its use method is very simple — the powder is carefully painted on a latent fingerprint to quickly obtain the fingerprint profile on a smooth substrate. Although this method is highly efficient and inexpensive, it has disadvantages such as high toxicity and contamination of DNA. Cyanoacrylate fuming, which originated at the end of the 20 th century, is commonly used to identify potential fingerprints on non-porous substrates. The identification mechanism is that vaporized cyanoacrylate monomer and residues in the fingerprint are rapidly polymerized, and then the polymerized monomer and unreacted monomer form white polymer to cover the protrusions in the fingerprint to achieve the effect of fingerprint color development. However, such a method also has disadvantages of high biotoxicity, long development time, low contrast, and the like. Therefore, it is necessary to develop a fluorescent material having low toxicity and rapidly recognizing a latent fingerprint.
In recent years, a variety of fluorescent materials, such as fluorescent quantum dots, rare earth up-conversion materials, and aggregation-induced emission materials, have low toxicity characteristics and have been used for identifying potential fingerprints. However, the conventional fluorescent materials have the disadvantages of low sensitivity, poor selectivity, slow development time, and the like. Moreover, because human fingerprints are usually composed of substances such as grease, inorganic salts, proteins and the like, the original appearance of the fingerprints may be damaged by the organic solvent for dissolving the lipophilic fluorescent material, so that the fingerprints cannot be distinguished or the identification degree is low, and the like. Therefore, it is necessary to develop a fluorescent material which has low toxicity, high sensitivity, good selectivity and fast color development time, and does not damage the original appearance of the fingerprint.
Disclosure of Invention
The invention aims to provide an amphiphilic host-guest fluorescent material for rapidly identifying potential fingerprints and a preparation method and application thereof.
In order to achieve the above object, the present invention provides the following technical solutions:
the invention provides a preparation method of an amphiphilic host-guest fluorescent material for rapidly identifying potential fingerprints, which comprises the following steps:
(1) dissolving 4-methylpyridine and 1-iodododecane in an organic solvent, and reacting at 55-90 ℃ for 1-36 h to obtain an intermediate;
(2) mixing the intermediate obtained in the step (1) with 4-dimethylaminobenzaldehyde, an alkaline reagent and ethanol, and carrying out hydroxy acid condensation reaction to obtain a hydrophobic hemicyanine fluorescent dye;
(3) and (3) mixing the hydrophobic hemicyanine fluorescent dye obtained in the step (2) with acetonitrile, beta-cyclodextrin and water, and reacting for 1-24 hours at 25-80 ℃ to obtain the amphiphilic host-guest fluorescent material.
Preferably, the ratio of the amount of 4-methylpyridine to 1-iodododecane in step (1) is (0.6-1.2): (0.8 to 1.4).
Preferably, the organic solvent in step (1) comprises acetonitrile, methanol or ethanol.
Preferably, the mass ratio of the intermediate, the 4-dimethylaminobenzaldehyde, the alkaline reagent and the ethanol in the step (2) is (0.6-1.4): (0.6-1.6): (0.006-1.6): (3-200).
Preferably, the temperature of the condensation reaction of the hydroxy acid in the step (2) is 50-90 ℃.
Preferably, the time of the condensation reaction of the hydroxy acid in the step (2) is 1-36 h.
Preferably, the alkaline agent in step (2) comprises piperidine, N-methylpiperidine or potassium carbonate.
Preferably, the mass ratio of the hydrophobic hemicyanine fluorescent dye, the acetonitrile, the beta-cyclodextrin and the water in the step (3) is (1-50): (1-3000): (1-10000): (100 to 600000).
The invention also provides an amphiphilic host-guest fluorescent material prepared by the preparation method of the technical scheme, which comprises beta-cyclodextrin serving as a host and hydrophobic hemicyanine fluorescent dye serving as a guest molecule, wherein the beta-cyclodextrin wraps the hydrophobic hemicyanine fluorescent dye to form an inclusion compound.
The invention also provides application of the amphiphilic host-guest fluorescent material in the technical scheme in rapid identification of potential fingerprints.
The invention provides a preparation method of an amphiphilic host-guest fluorescent material for rapidly identifying potential fingerprints, which comprises the following steps: dissolving 4-methylpyridine and 1-iodododecane in an organic solvent, and reacting at 55-90 ℃ for 1-36 h to obtain an intermediate; mixing the obtained intermediate with 4-dimethylaminobenzaldehyde, an alkaline reagent and ethanol, and carrying out hydroxy acid condensation reaction to obtain a hydrophobic hemicyanine fluorescent dye; and mixing the obtained hydrophobic hemicyanine fluorescent dye with acetonitrile, beta-cyclodextrin and water, and reacting for 1-24 h at 25-80 ℃ to obtain the amphiphilic host-guest fluorescent material. The method comprises the steps of firstly preparing a hydrophobic hemicyanine fluorescent dye, then mixing the obtained hydrophobic hemicyanine fluorescent dye with acetonitrile, beta-cyclodextrin and water, and carrying out host-guest inclusion on the hydrophobic hemicyanine fluorescent dye and the beta-cyclodextrin to obtain the hydrophobic hemicyanine fluorescent dye comprising the beta-cyclodextrin serving as a host and guest molecules. In the invention, the hydrophobic hemicyanine fluorescent dye has the characteristic of low toxicity, so that the toxicity hazard of the operation of displaying potential fingerprints can be reduced; the hydrophobic fluorescent dye is easily wrapped by the beta-cyclodextrin with the outer edge hydrophilic inner cavity hydrophobic, so that the amphiphilic host-guest fluorescent material can be completely dissolved in deionized water, and the aqueous solution prepared from the host-guest fluorescent material can be quickly combined with grease in fingerprints, can be suitable for displaying potential fingerprints on different carriers, and has higher selectivity; and because the aqueous solution prepared from the host-guest fluorescent material is used, no organic solvent exists, the host-guest fluorescent material and the grease can be combined for color development on the premise of not damaging the grease traces in the fingerprint, and the sensitivity is higher. Experimental results show that the amphiphilic host-guest fluorescent material prepared by the invention is dissolved in deionized water, and the glass sheet printed with the fingerprint is soaked in the aqueous solution of the amphiphilic host-guest fluorescent material for 10s and then taken out, so that the potential fingerprint can be displayed within 5s, the sensitivity is high, and the display time is short; when the fingerprints are printed on different substrates and detected by adopting the method, the potential fingerprints can still be quickly displayed, and the selectivity for displaying the potential fingerprints is high.
Drawings
FIG. 1 is a schematic diagram illustrating the principle of preparing an amphiphilic host-guest fluorescent material in embodiments 1 to 9 of the present invention;
FIG. 2 is a nuclear magnetic hydrogen spectrum of the hydrophobic hemicyanine fluorescent dye prepared in example 1;
FIG. 3 is an SEM photograph of an amphiphilic host-guest fluorescent material prepared in example 1;
FIG. 4 is XRD patterns of β -cyclodextrin, the hydrophobic hemicyanine fluorescent dye prepared in example 1, and the amphiphilic host-guest fluorescent material;
FIG. 5 is a FT-IR chart of β -cyclodextrin, the hydrophobic hemicyanine fluorescent dye prepared in example 1, and the amphiphilic host-guest fluorescent material;
FIG. 6 is a photograph showing the time at which fingerprints appear in application example 1;
FIG. 7 is a photograph of fingerprints on different substrates in application example 2;
FIG. 8 is a photograph showing the effect of fingerprint effect by comparing the amounts of substances of I and beta-CD in application example 3.
Detailed Description
The invention provides a preparation method of an amphiphilic host-guest fluorescent material for rapidly identifying potential fingerprints, which comprises the following steps:
(1) dissolving 4-methylpyridine and 1-iodododecane in an organic solvent, and reacting at 55-90 ℃ for 1-36 h to obtain an intermediate;
(2) mixing the intermediate obtained in the step (1) with 4-dimethylaminobenzaldehyde, an alkaline reagent and ethanol, and carrying out hydroxy acid condensation reaction to obtain a hydrophobic hemicyanine fluorescent dye;
(3) and (3) mixing the hydrophobic hemicyanine fluorescent dye obtained in the step (2) with acetonitrile, beta-cyclodextrin and water, and reacting for 1-24 hours at 25-80 ℃ to obtain the amphiphilic host-guest fluorescent material.
The method comprises the steps of dissolving 4-methylpyridine and 1-iodododecane in an organic solvent, and reacting for 1-36 hours at 55-90 ℃ to obtain an intermediate.
In the present invention, the ratio of the amounts of the 4-methylpyridine and 1-iodododecane is preferably (0.6 to 1.2): (0.8 to 1.4), more preferably (0.8 to 1.0): (1.0-1.2). The sources of the 4-methylpyridine and the 1-iodododecane are not particularly limited in the present invention, and commercially available products known to those skilled in the art may be used. In the present invention, the 4-picolination reaction between the 4-picoline and 1-iodododecane takes place, and when the ratio of the amounts of the 4-picoline to 1-iodododecane is in the above range, the 4-picolination reaction is facilitated.
In the present invention, the organic solvent preferably includes acetonitrile, methanol or ethanol. The source of the organic solvent is not particularly limited in the present invention, and a commercially available product known to those skilled in the art may be used. In the present invention, the volume ratio of the amount of the substance of 4-methylpyridine to the organic solvent is preferably (0.6 to 1.2) mol: (30-60) mL.
The operation mode of dissolving the 4-methylpyridine and the 1-iodododecane in the organic solvent is not particularly limited in the present invention, and the operation mode known to those skilled in the art can be adopted.
In the invention, the reaction temperature of the 4-methylpyridine and the 1-iodododecane in the organic solvent is preferably 60-85 ℃, and more preferably 70-80 ℃; the reaction time of the 4-methylpyridine and the 1-iodododecane in the organic solvent is preferably 5-30 hours, and more preferably 10-24 hours. In the present invention, when the temperature and time of the reaction are within the above ranges, it is more advantageous to promote the progress of the 4-picolination reaction.
In the present invention, the reaction of 4-methylpyridine with 1-iodododecane in an organic solvent is preferably carried out under reflux with stirring. The present invention does not specifically limit the speed of the reflux stirring, and the components can be sufficiently mixed. In the present invention, the reflux stirring can prevent escape of reactant or solvent vapor due to the long reaction time.
After the reaction of 4-methylpyridine with 1-iodododecane in an organic solvent is completed, the present invention preferably removes the solvent from the product obtained by the reaction to obtain an intermediate. The solvent removal operation is not particularly limited in the present invention, and a solvent removal method known to those skilled in the art may be used. In the present invention, the solvent is preferably removed by heating evaporation. In the invention, the heating and evaporating temperature is preferably 25-100 ℃, and more preferably 50-80 ℃. The time for heating and evaporating is not particularly limited, and the solvent in the product obtained by the reaction can be removed by adjusting the amount of the solvent in the product obtained by the reaction. In the invention, the heating and evaporating time is preferably 2-8 h, and more preferably 4-6 h.
After the intermediate is obtained, the intermediate is mixed with 4-dimethylaminobenzaldehyde, an alkaline reagent and ethanol to carry out hydroxy acid condensation reaction, and the hydrophobic hemicyanine fluorescent dye is obtained. The present invention is not particularly limited to the manner of mixing the intermediate with 4-dimethylaminobenzaldehyde, an alkaline agent and ethanol, and the mixing of the intermediate with the agent known to those skilled in the art may be carried out.
In the present invention, the alkali agent preferably includes piperidine, N-methylpiperidine or potassium carbonate, more preferably N-methylpiperidine. In the present invention, the alkaline reagent provides a weakly alkaline environment for the hydroxy acid condensation reaction, catalyzing the hydroxy acid condensation reaction. The source of the alkaline agent is not particularly limited in the present invention, and commercially available products known to those skilled in the art may be used.
In the invention, the amount ratio of the intermediate to the substances of 4-dimethylaminobenzaldehyde, the alkaline reagent and ethanol is preferably (0.6-1.4): (0.6-1.6): (0.006-1.6): (3-200), more preferably (0.8-1.2): (0.8-1.4): (0.01-1.0): (10-100). In the present invention, when the ratio of the amount of the intermediate to the substances of 4-dimethylaminobenzaldehyde, the basic agent and ethanol is in the above range, the progress of the hydroxy acid condensation reaction is more facilitated. The sources of the 4-dimethylaminobenzaldehyde and ethanol are not particularly limited in the present invention, and commercially available products known to those skilled in the art may be used.
In the invention, the temperature of the hydroxy acid condensation reaction is preferably 50-90 ℃, and more preferably 60-80 ℃; the time of the condensation reaction of the hydroxy acid is preferably 1 to 36 hours, and more preferably 10 to 24 hours. In the present invention, when the temperature and time of the hydroxy acid condensation reaction are within the above ranges, the progress of the hydroxy acid condensation reaction is more favorably accelerated.
After completion of the hydroxy acid condensation reaction, the present invention preferably recrystallizes the product of the hydroxy acid condensation reaction to yield the hydrophobic hemicyanine fluorescent dye. The present invention is not particularly limited in the manner of recrystallization of the product of the hydroxy acid condensation reaction, and a recrystallization method known to those skilled in the art may be used. In the present invention, the reagent used for recrystallization preferably includes a mixed solution of ethanol and water, a mixed solution of methanol and water, or dimethyl sulfoxide. In the present invention, the volume ratio of ethanol to water in the mixed solution of ethanol and water is preferably 10: 1; the volume ratio of methanol to water in the mixed liquid of methanol and water is preferably 10: 1. in the present invention, the recrystallization enables purification of the product of the hydroxy acid condensation reaction to give hydrophobic hemicyanine fluorescent dyes.
In the present invention, the reaction for preparing the hydrophobic hemicyanine fluorescent dye is preferably as shown in formula I:
according to the formula I, 4-methylpyridine and 1-iodododecane are dissolved in an organic solvent acetonitrile and react for 1-36 h at 55-90 ℃ to obtain an intermediate; mixing the intermediate with 4-dimethylaminobenzaldehyde, an alkaline reagent N-methylpiperidine and ethanol, and carrying out hydroxy acid condensation reaction to obtain the hydrophobic hemicyanine fluorescent dye.
After the hydrophobic hemicyanine fluorescent dye is obtained, the hydrophobic hemicyanine fluorescent dye is mixed with acetonitrile, beta-cyclodextrin and water, and reacts for 1-24 hours at the temperature of 25-80 ℃ to obtain the amphiphilic host-guest fluorescent material.
In the invention, the mass ratio of the hydrophobic hemicyanine fluorescent dye to the acetonitrile to the beta-cyclodextrin to the water is preferably (1-50): (1-3000): (1-10000): (100 to 600000), more preferably (1 to 10): (2-400): (2-5000): (200-40000). In the invention, when the mass ratio of the hydrophobic hemicyanine fluorescent dye to the acetonitrile to the beta-cyclodextrin to the water is in the above range, the hydrophobic hemicyanine fluorescent dye is favorable for performing host-guest inclusion with a mixed solution obtained from the acetonitrile to the beta-cyclodextrin to wrap the hydrophobic hemicyanine fluorescent dye with the beta-cyclodextrin, the outer edge of which is hydrophilic and the inner cavity of which is hydrophobic.
The method for mixing the hydrophobic hemicyanine fluorescent dye with acetonitrile, beta-cyclodextrin and water is not particularly limited, and the hydrophobic hemicyanine fluorescent dye and the beta-cyclodextrin can be dissolved in water and acetonitrile by adopting a solid-liquid mixing method well known to those skilled in the art.
In the invention, the reaction temperature of the hydrophobic hemicyanine fluorescent dye, acetonitrile, beta-cyclodextrin and water is preferably 30-70 ℃, and more preferably 40-60 ℃; the reaction time of the hydrophobic hemicyanine fluorescent dye, acetonitrile, beta-cyclodextrin and water is preferably 5-20 h, and more preferably 15-20 h. In the present invention, when the temperature and time of the reaction are within the above ranges, the inclusion of the host and guest is facilitated.
After the reaction of the hydrophobic hemicyanine fluorescent dye, acetonitrile, beta-cyclodextrin and water is finished, the invention preferably cools, filters and dries the reacted system in sequence to obtain the amphiphilic host-guest fluorescent material.
In the invention, the final temperature of the temperature reduction is preferably 1-10 ℃, and more preferably 4-8 ℃. The operation of cooling is not particularly limited, and the temperature of the system after the mixed solution reacts at 25-80 ℃ can be cooled to 1-10 ℃. In the invention, the temperature of the system after the mixed solution reacts at 25-80 ℃ is reduced, so that crystals formed by inclusion of the host and the guest can be separated out, and separation of the beta-cyclodextrin-coated hydrophobic fluorescent dye, namely the amphiphilic host and guest fluorescent material, is facilitated.
The operation method of the invention is not specially limited, and the crystal formed by the inclusion of the host and the guest can be separated from the system after the temperature is reduced.
In the invention, the drying temperature is preferably 25-100 ℃, and more preferably 50-80 ℃; the drying time is preferably 2-8 h, and more preferably 4-6 h. In the present invention, the drying can remove the solvent in the amphiphilic host-guest fluorescent material.
In the present invention, a schematic diagram of a principle of preparing the amphiphilic host-guest fluorescent material is shown in fig. 1. As can be seen from fig. 1, the hydrophobic fluorescent dye can be encapsulated by the β -cyclodextrin, so as to obtain the amphiphilic host-guest fluorescent material.
The invention provides a preparation method of an amphiphilic host-guest fluorescent material for rapidly identifying potential fingerprints.
The invention also provides the amphiphilic host-guest fluorescent material prepared by the preparation method in the technical scheme, which comprises beta-cyclodextrin serving as a host and hydrophobic hemicyanine fluorescent dye serving as a guest molecule, wherein the beta-cyclodextrin wraps the hydrophobic hemicyanine fluorescent dye to form an inclusion compound.
In the present invention, the ratio of the amounts of the beta-cyclodextrin and the hydrophobic hemicyanine fluorescent dye is preferably (1 to 4000): (1-10), more preferably (1-10): (1-5). In the invention, when the mass ratio of the beta-cyclodextrin to the hydrophobic hemicyanine fluorescent dye is in the above range, the amphiphilic host-guest fluorescent material is favorably combined with the grease in the fingerprint, and the fingerprint is more favorably displayed.
In the invention, the amphiphilic host-guest fluorescent material comprises beta-cyclodextrin of a host and hydrophobic hemicyanine fluorescent dye as a guest molecule. The beta-cyclodextrin used as the main material has the characteristic that the outer cavity is hydrophilic and the inner cavity is hydrophobic, and after the beta-cyclodextrin and the outer cavity are included, the characteristic of amphiphilicity can be shown, namely, the beta-cyclodextrin is hydrophilic and oleophilic. The hydrophobic hemicyanine fluorescent dye has the characteristic of low toxicity; the hydrophobic fluorescent dye is easily wrapped by the beta-cyclodextrin with the hydrophilic outer edge and the hydrophobic inner cavity, so that the amphiphilic host-guest fluorescent material can be completely dissolved in deionized water.
The invention also provides application of the amphiphilic host-guest fluorescent material in the technical scheme in rapid identification of potential fingerprints.
In the present invention, the application preferably includes: preparing an aqueous solution of the amphiphilic host-guest fluorescent material, soaking the substrate printed with the fingerprint in the aqueous solution of the amphiphilic host-guest fluorescent material, taking out the substrate, and shooting the fingerprint by using a camera under the irradiation of an ultraviolet flashlight.
In the present invention, the ratio of the mass of the amphiphilic host-guest fluorescent material to the volume of water in the aqueous solution of the amphiphilic host-guest fluorescent material is preferably (1 to 200) mg: (2-200) mL, more preferably (50-100) mg: (50-100) mL. In the present invention, when the concentration of the aqueous solution of the amphiphilic host-guest fluorescent material is in the above range, it is more advantageous to display fingerprints.
The source of the substrate on which the fingerprint is printed is not particularly limited in the present invention, and a flat or rough flat surface may be used. In the present invention, the fingerprint-printed substrate preferably includes one or more of a glass sheet, an aluminum foil, a tin foil, a copper foil, a plastic, a brick, and a leaf. In the invention, the aqueous solution of the amphiphilic host-guest fluorescent material has excellent sensitivity on fingerprint display, so that the fluorescent material can be suitable for various types of substrates.
The present invention is not particularly limited to the operation of printing a fingerprint on the substrate, and may be performed in a manner known to those skilled in the art. In the present invention, the operation of printing a fingerprint on the substrate preferably includes: the index finger of the experimenter dips a small amount of a mixture of lauric triglyceride and oleic acid, which is then printed on a glass plate to obtain a substrate printed with the experimenter's fingerprint.
In the invention, the time for soaking the substrate printed with the fingerprint in the aqueous solution of the amphiphilic host-guest fluorescent material is preferably (1-60) s, and more preferably (1-10) s. In the invention, since the aqueous solution of the amphiphilic host-guest fluorescent material has excellent sensitivity to fingerprint development, the amphiphilic host-guest fluorescent material can be combined with the grease on the fingerprint only by soaking the substrate printed with the fingerprint in the aqueous solution of the amphiphilic host-guest fluorescent material for the time within the above range.
In the invention, the wavelength of the ultraviolet flashlight is preferably 365-450 nm, and more preferably (365-395) nm. In the invention, when the wavelength of the ultraviolet flashlight is within the range, the amphiphilic host-guest fluorescent material has a more obvious color development effect, and is beneficial to observing the appearance of fingerprints.
The amphiphilic host-guest fluorescent material provided by the invention has the characteristic of low toxicity, and can reduce the toxicity hazard of displaying potential fingerprint operation; the amphiphilic host-guest fluorescent material provided by the invention has the property of being completely dissolved in deionized water, and an aqueous solution prepared from the host-guest fluorescent material can be quickly combined with grease in fingerprints, can be suitable for displaying potential fingerprints on different carriers, and has high selectivity; and because the aqueous solution prepared from the host-guest fluorescent material is used, no organic solvent exists, the host-guest fluorescent material and the grease can be combined for color development on the premise of not damaging the grease traces in the fingerprint, and the sensitivity is higher.
The technical solution of the present invention will be clearly and completely described below with reference to the embodiments of the present invention. It is to be understood that the described embodiments are merely exemplary of the invention, and not restrictive of the full scope of the invention. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
(1) Dissolving 1mol of 4-methylpyridine and 1mol of 1-iodododecane in 50mL of acetonitrile, and carrying out reflux stirring at 80 ℃ to react for 24h to obtain an intermediate; (wherein the amount ratio of 4-methylpyridine, 1-iodododecane and acetonitrile is 1 mol: 1 mol: 50mL)
(2) Mixing the intermediate obtained in the step (1) with 1mol of 4-dimethylaminobenzaldehyde, 0.002mol of piperidine and 1mol of ethanol, reacting at 80 ℃ for 16h, carrying out hydroxy acid condensation reaction, and recrystallizing by using dimethyl sulfoxide to obtain hydrophobic hemicyanine fluorescent dye (hereinafter referred to as I); (wherein the ratio of the amounts of the intermediate, 4-dimethylaminobenzaldehyde, piperidine and ethanol is 1: 1: 0.5: 50)
(3) And (3) mixing 0.4g of the hydrophobic hemicyanine fluorescent dye obtained in the step (2) with 1g of acetonitrile, 2.4g of beta-cyclodextrin and 100g of water, and reacting at 70 ℃ for 8h to obtain the amphiphilic host-guest fluorescent material (hereinafter referred to as I/beta-CD), wherein the amount of substances of I and beta-CD in the I/beta-CD is 1: 3.
The hydrophobic hemicyanine fluorescent dye I prepared in this example was detected by a nuclear magnetic resonance spectrometer, and the nuclear magnetic hydrogen spectrum obtained is shown in fig. 2. From FIG. 2, it can be seen that the structural formula of the hydrophobic hemicyanine fluorescent dye I is formula (II):
the I/β -CD prepared in this example was observed by a scanning electron microscope to obtain an SEM image as shown in FIG. 3. In FIG. 3, the scale is 200 μm in size. As can be seen from FIG. 3, the I/beta-CD has a rhombic shape and a size of 50-300 μm.
When beta-cyclodextrin (hereinafter referred to as beta-CD) and I, I/beta-CD prepared in this example were observed by X-ray diffraction, XRD patterns were shown in FIG. 4. As can be seen in FIG. 4, the peak positions of I/β -CD are different from those of I and β -CD, demonstrating that the crystal form is changed.
Beta-cyclodextrin (hereinafter referred to as beta-CD) and I, I/beta-CD prepared in this example were observed by Fourier transform infrared spectroscopy, respectively, to obtain FT-IR chart, as shown in FIG. 5. As can be seen from FIG. 5, the peak positions of both I and β -CD can be found in I/β -CD, demonstrating that I/β -CD possesses both I and β -CD species. Fig. 4 and fig. 5 show that the I/β -CD prepared in this example successfully forms an amphiphilic host-guest fluorescent material, which includes β -cyclodextrin as a host and hydrophobic hemicyanine fluorescent dye as a guest molecule, to form an inclusion compound of a host-encapsulated guest.
Example 2
The preparation method of the steps (1) and (2) in the embodiment 1 is adopted to prepare the hydrophobic hemicyanine fluorescent dye (I);
(3) mixing 0.005g of hydrophobic hemicyanine fluorescent dye obtained in the step (2) with 1g of acetonitrile, 0.025g of beta-cyclodextrin and 100g of water, and reacting at 70 ℃ for 8h to obtain the amphiphilic host-guest fluorescent material (hereinafter referred to as I/beta-CD), wherein the amount of substances of I and beta-CD in the I/beta-CD is 2: 5.
Example 3
The preparation method of the steps (1) and (2) in the example 1 is adopted to prepare the hydrophobic hemicyanine fluorescent dye;
(3) mixing 0.005g of hydrophobic hemicyanine fluorescent dye obtained in the step (2) with 1g of acetonitrile, 0.25g of beta-cyclodextrin and 100g of water, and reacting at 70 ℃ for 8h to obtain the amphiphilic host-guest fluorescent material (hereinafter referred to as I/beta-CD), wherein the molar ratio of I to beta-CD in the I/beta-CD is 2: 50.
Example 4
The preparation method of the steps (1) and (2) in the example 1 is adopted to prepare the hydrophobic hemicyanine fluorescent dye;
(3) mixing 0.005g of hydrophobic hemicyanine fluorescent dye obtained in the step (2) with 1g of acetonitrile, 0.45g of beta-cyclodextrin and 100g of water, and reacting at 70 ℃ for 8h to obtain the amphiphilic host-guest fluorescent material (hereinafter referred to as I/beta-CD), wherein the molar ratio of I to beta-CD in the I/beta-CD is 2: 90.
Example 5
The preparation method of the steps (1) and (2) in the example 1 is adopted to prepare the hydrophobic hemicyanine fluorescent dye;
(3) mixing 0.005g of hydrophobic hemicyanine fluorescent dye obtained in the step (2) with 1g of acetonitrile, 1.25g of beta-cyclodextrin and 100g of water, and reacting at 70 ℃ for 8h to obtain the amphiphilic host-guest fluorescent material (hereinafter referred to as I/beta-CD), wherein the molar ratio of I to beta-CD in the I/beta-CD is 2: 250.
Example 6
The preparation method of the steps (1) and (2) in the example 1 is adopted to prepare the hydrophobic hemicyanine fluorescent dye;
(3) mixing 0.005g of hydrophobic hemicyanine fluorescent dye obtained in the step (2) with 1g of acetonitrile, 1.75g of beta-cyclodextrin and 100g of water, and reacting at 70 ℃ for 8h to obtain the amphiphilic host-guest fluorescent material (hereinafter referred to as I/beta-CD), wherein the molar ratio of I to beta-CD in the I/beta-CD is 2: 350.
Example 7
The preparation method of the steps (1) and (2) in the example 1 is adopted to prepare the hydrophobic hemicyanine fluorescent dye;
(3) mixing 0.005g of hydrophobic hemicyanine fluorescent dye obtained in the step (2) with 1g of acetonitrile, 2.0g of beta-cyclodextrin and 100g of water, and reacting at 70 ℃ for 8h to obtain the amphiphilic host-guest fluorescent material (hereinafter referred to as I/beta-CD), wherein the molar ratio of I to beta-CD in the I/beta-CD is 2: 400.
Example 8
The preparation method of the steps (1) and (2) in the example 1 is adopted to prepare the hydrophobic hemicyanine fluorescent dye;
(3) mixing 0.005g of hydrophobic hemicyanine fluorescent dye obtained in the step (2) with 1g of acetonitrile, 5g of beta-cyclodextrin and 100g of water, and reacting at 70 ℃ for 8h to obtain the amphiphilic host-guest fluorescent material (hereinafter referred to as I/beta-CD), wherein the molar ratio of I to beta-CD in the I/beta-CD is 2: 1000.
Example 9
The preparation method of the steps (1) and (2) in the example 1 is adopted to prepare the hydrophobic hemicyanine fluorescent dye;
(3) mixing 0.005g of hydrophobic hemicyanine fluorescent dye obtained in the step (2) with 1g of acetonitrile, 10g of beta-cyclodextrin and 100g of water, and reacting at 70 ℃ for 8h to obtain the amphiphilic host-guest fluorescent material (hereinafter referred to as I/beta-CD), wherein the molar ratio of I to beta-CD in the I/beta-CD is 2: 2000.
Application example 1
(1) Dipping the mixture of lauric triglyceride and oleic acid by the index finger of an experimenter, and then printing the mixture on a glass sheet to obtain the glass sheet printed with the fingerprint of the experimenter;
(2) the I/beta-CD prepared in example 1 was prepared into an aqueous solution having a concentration of 10mg/mL, and the glass plate on which the fingerprint was printed was immersed in the aqueous solution of I/beta-CD for 10 seconds. Then taking out, and taking a fingerprint by using a camera under the irradiation of an ultraviolet flashlight with the wavelength of 395nm, and taking a picture every 2s to obtain a picture of the time for developing the color of the fingerprint as shown in FIG. 6.
As can be seen from FIG. 6, the fingerprint was stained rapidly after being immersed in an aqueous solution of I/β -CD, and reached an optimum brightness at 5 seconds, with a fast development time.
Application example 2
(1) The index finger of the experimenter dips in the mixture of lauric triglyceride and oleic acid, and then prints on different substrates to obtain the fingerprint substrate printed with the experimenter, wherein the substrates are tin foil, copper foil, plastic, leaves, bricks and glass respectively.
(2) The I/beta-CD prepared in example 1 was prepared into an aqueous solution having a concentration of 10mg/mL, and the fingerprint-printed substrate was immersed in the aqueous solution of I/beta-CD for 10 seconds. The film was then removed and a fingerprint was taken with a camera under the 395nm UV flashlight illumination, and the resulting photograph is shown in FIG. 7.
As can be seen from fig. 7, by immersing different substrates printed with fingerprints in an aqueous solution of I/β -CD, we found that the color development effect was the best on smooth substrates, such as glass sheets, aluminum foil and copper foil; but also has a significant color development effect on rough substrates. The result shows that the aqueous solution prepared by the I/beta-CD prepared by the invention not only can be suitable for fingerprint display on a smooth substrate, but also can be suitable for fingerprint display on a rough substrate, and has better selectivity on fingerprints and excellent sensitivity.
Application example 3
(1) The index finger of the experimenter dips in the mixture of the lauric triglyceride and the oleic acid, and then the mixture is printed on 8 glass sheets respectively to obtain the fingerprint glass sheets printed with the experimenter, wherein the fingerprint glass sheets printed with the experimenter are numbered a-h in sequence.
(2) The I/beta-CD prepared in the examples 2 to 9 is prepared into aqueous solution with the concentration of 10mg/mL respectively, and the glass sheet printed with the fingerprint is soaked in the aqueous solution of the I/beta-CD for 10 s. Subsequently, the film was taken out and the fingerprint was photographed by a camera under the irradiation of a torch at 395nm, and a photograph showing the influence of the fingerprint effect by the ratio of the amounts of the substances of I and beta-CD was obtained as shown in FIG. 8. In FIG. 8, the scale is 500 μm, and the glass sheets a to h are sequentially and correspondingly numbered a to h and immersed in the aqueous solution of I/β -CD prepared in examples 2 to 9, and then photographed by a camera with the irradiation of a flashlight of 395 nm.
As can be seen from fig. 8, as the ratio of the amounts of I to β -CD substances in the I/β -CD aqueous solution increases, the liquid formed on the fingerprint gradually changes to crystals, and as is evident from the two last figures, crystals precipitate, and such a solid can better image the fingerprint on a rough surface than a liquid.
The foregoing is only a preferred embodiment of the present invention, and it should be noted that, for those skilled in the art, various modifications and decorations can be made without departing from the principle of the present invention, and these modifications and decorations should also be regarded as the protection scope of the present invention.
Claims (10)
1. A preparation method of an amphiphilic host-guest fluorescent material for rapidly identifying potential fingerprints comprises the following steps:
(1) dissolving 4-methylpyridine and 1-iodododecane in an organic solvent, and reacting at 55-90 ℃ for 1-36 h to obtain an intermediate;
(2) mixing the intermediate obtained in the step (1) with 4-dimethylaminobenzaldehyde, an alkaline reagent and ethanol, and carrying out hydroxy acid condensation reaction to obtain a hydrophobic hemicyanine fluorescent dye;
(3) and (3) mixing the hydrophobic hemicyanine fluorescent dye obtained in the step (2) with acetonitrile, beta-cyclodextrin and water, and reacting for 1-24 hours at 25-80 ℃ to obtain the amphiphilic host-guest fluorescent material.
2. The method according to claim 1, wherein the ratio of the amounts of 4-methylpyridine to 1-iodododecane in step (1) is (0.6 to 1.2): (0.8 to 1.4).
3. The method according to claim 1, wherein the organic solvent in the step (1) comprises acetonitrile, methanol or ethanol.
4. The method according to claim 1, wherein the amount ratio of the intermediate, 4-dimethylaminobenzaldehyde, alkaline agent and ethanol in step (2) is (0.6 to 1.4): (0.6-1.6): (0.006-1.6): (3-200).
5. The method according to claim 1, wherein the temperature of the condensation reaction of the hydroxy acid in the step (2) is 50 to 90 ℃.
6. The method according to claim 1 or 5, wherein the time for the condensation reaction of the hydroxy acid in the step (2) is 1 to 36 hours.
7. The method according to claim 1, wherein the basic agent in the step (2) comprises piperidine, N-methylpiperidine or potassium carbonate.
8. The preparation method according to claim 1, wherein the mass ratio of the hydrophobic hemicyanine fluorescent dye, the acetonitrile, the beta-cyclodextrin and the water in the step (3) is (1-50): (1-3000): (1-10000): (100 to 600000).
9. An amphiphilic host-guest fluorescent material prepared by the preparation method according to any one of claims 1 to 8, which comprises beta-cyclodextrin serving as a host and hydrophobic hemicyanine fluorescent dye serving as a guest molecule, wherein the beta-cyclodextrin wraps the hydrophobic hemicyanine fluorescent dye to form an inclusion compound.
10. Use of the amphiphilic host-guest fluorescent material according to claim 9 for rapid identification of latent fingerprints.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114436948A (en) * | 2022-01-19 | 2022-05-06 | 上海工程技术大学 | Dipyridyl triphenylamine aldehyde fluorescent material with aggregation-induced emission effect and preparation method and application thereof |
| CN116179189A (en) * | 2022-12-30 | 2023-05-30 | 上海宇昂水性新材料科技股份有限公司 | Fluorescent material and preparation method and application thereof |
| CN116179189B (en) * | 2022-12-30 | 2024-05-17 | 上海宇昂水性新材料科技股份有限公司 | Fluorescent material and preparation method and application thereof |
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| US6485981B1 (en) * | 1998-07-29 | 2002-11-26 | Ciencia, Inc. | Method and apparatus for imaging and documenting fingerprints |
| CN111303867A (en) * | 2020-02-21 | 2020-06-19 | 华中科技大学 | Application of diarylethene compounds in fingerprint fluorescence color development |
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| US6485981B1 (en) * | 1998-07-29 | 2002-11-26 | Ciencia, Inc. | Method and apparatus for imaging and documenting fingerprints |
| CN111303867A (en) * | 2020-02-21 | 2020-06-19 | 华中科技大学 | Application of diarylethene compounds in fingerprint fluorescence color development |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114436948A (en) * | 2022-01-19 | 2022-05-06 | 上海工程技术大学 | Dipyridyl triphenylamine aldehyde fluorescent material with aggregation-induced emission effect and preparation method and application thereof |
| CN116179189A (en) * | 2022-12-30 | 2023-05-30 | 上海宇昂水性新材料科技股份有限公司 | Fluorescent material and preparation method and application thereof |
| CN116179189B (en) * | 2022-12-30 | 2024-05-17 | 上海宇昂水性新材料科技股份有限公司 | Fluorescent material and preparation method and application thereof |
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